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INTERBIOSCREEN

..

547.7/.8:615.011
24.23
X=46

, 2 /
.. . .: IBS PRESS

. , ,
, IBS PRESS.
press@ibscreen.chg.ru

ISBN 5-93584-009-

IBS PRESS, 2003

..


Bergman J.
Corey E.J.
Huisgen R.

(Sweden)
(USA)
(Germany)

Katritzky A.R.
Noyori R.
Van der Plas H.C.

(USA)
(Japan)
(Netherlands)


..
..
..
..
..
..
..

()
()
()
()
()
()
()

..
..
..
..
..
..

()
()
()
()
()
()


..
..
..
..
..
..
..

()
()
()
()
()
()
()

..
..
..
..
..
..
..

()
()
()
()
()
()
()

..
..
..

..

..
..
..


-
, , ,
"
" ( , ,
2003 ., : IBS PRESS, 2003).

.

- S-, -, , .
2-
" - "
(, 1417 2003 .) "
",
" ", InterBioScreen,
,
.


. ( 1990 .), ;
. (
2001 .), ; ,
:
. , , ; . , , ; . ,
, ; . , , , , .

.
, , , ,
, , , .

- InterBioScreen

" "

.., ..
C ........................ 7
..

2- ............................................................................................. 25
..
............. 36
..

......................................................................................... 63
.., ..

.................................................................. 75
.., .., .., ..
- ...................... 103
.., ..
- ......................... 113
.., ..

......................................................................... 127
.., .., ..
................................................................. 149
.., .., .., ..
.................................................................................................. 159
.., ..
2- ................................................................... 193
.., .., .., .., ..
......................................... 206
.., ..
-
................................................................................ 241
, 2

..
.
2. , ......................................................................... 258
.., .., ..
- ............... 284
.., .., ..
1,4- ................................................. 305
.., ..
1,3-
-, -
.............................................................................................................. 335
.., ..
4,5-
2,3--2,3- ................................................................................... 361
..
-4,5- ....................................... 396
.., .., ..
- ,
,- ............................ 405
.., .., ..
3-
.................................................................................................................... 437
..
,
[2,3-c] [2,3-c].................................. 444
..

............................................................... 465
.., .., ..
................................. 493
.., ..
3-- 3- ....................................................................... 503
.., .., ..
: .......................................................................... 518
.., a ..
2--4- .............. 534
........................................................................................ 564565
6

InterBioScreen

C

.., ..

470032, , . , 4

[18]
,
[915], [1630], [3135],
[36], [37], [38],
[3940], [41] .
, , - , ,-
[42].

S
H

R
O

S
R

,

,
[4345].
, , , 1, - 2 3 . 1
.
- 2 3 .
O

H
O
O
O
H O
1

O
O

O
2

, 2

-
, ,
4a, b 5,
Eupatorium sachalinense [10] Artemisia
glabella Kar. et Kir [15].

OR
O
AcO

O
O

OH

; 4b R =

4a R =

OH

OH

, . 6,
, -
- - . 7
[1].

O
O

OH

O
H O
6

O
O

HO
7

, . [46]
8 9,
Tanacetum parthenium (L.) Schulz Bip.
1013 .
1112 45 , 13 24 9.
8

InterBioScreen

O O

OH

O
O

OR

10

11 R = H;
12 R = Na;
13 R = K

10, -
, .
,
,
.
, "" . ,
,

, - , ..



"". , , 14,
Ajania fruticulosa (Ldb.) Poljak.
15.
1415 [47].
Na2CO3

AcO

Me2CO H2O 1:1

HO

O
O

O
14

15

, 2

[48].
16 - .

H2

NaOH

A
O

OH

B
H

CO2H

OH

CO2H

O
2

2a

16

,
. [49]
.
1,7,10H--4,11--3- 19 20.

H
Zn,

AcOH, H2O

17

OH

18 (86%)

19

20

OH

. , , 21
22.
-
(5), 22 [50].
10

InterBioScreen

O NO2

NO2

NO2

O NO2

+
H

Py
5

+
PyH

NO2

O NO2

O
O

O
O

OH

21a

21

22

[51].
,

(. 1). 2527
, (+)--
.

O
O
O

H O

O
O

23

24

O
O
25a R = N

26a R = N
;

25b R = N
25c R = N

R
;

27 R = N

26b R = N

26c R = N

, 2

11

1.

2
2
2
23
23
23
24

25
60
60
25
60
60
25

,
%

, %

3.5
36
36
4
36
36
4

100
92
69
100
93
75
100

5.5
7
7
5.5
7
7
5.5

25a
25b
25c
26a
26b
26c
27

78
57
24
78
58
34
65

---
- [52]. , , - 2930. - 2 LDA
78
- 28, 29 ,
[53].
(PhSe)2 , 30.
LDA, 78C
(PhSe)2

SePh

O
O

28

LDA, 78C
CH2=CHCH2Br

H2O2

O
30

O
29

[54] 32. 31 H2O2


32 ,- .
12

InterBioScreen

15

LDA, PhSeCl
H2O2, AcOH,

O
O

O
2

31

O
O

O
O

32

,-
[55].
35
33. ().
,-
35 87%.

TMSO

HO
TMSOTf, Et3N

PTAB

CH2Cl2

O
OTMS

O
33

33a

TMSO

HO
Bu4NF,

Br

O
34

O
35

, 2

13

,- --
,- ,
,
, , . ,
[5657] , 11,13--13-1,10--5,7,6()--3(4)--6,12- 37.
14

Me2NH

HCl

10

2
3

15

8
7

H
11

12

13

HCl
N

37

36

37 , (11) S- [58].
3843 4448,
[59], 4951, 5255, [60]. 53 ,
(11) R-.
OH

OH

O
R

OH

38 R = NMe2;
39 R = NEt2;
40 R = N(CH2CH2OH)2;
41 R = NBu2;

44 R = NMe2;
45 R = NEt2;
44 R = NBu2;

O
R

OH

49 R = NEt2;
50 R = NMe2;
51 R = N
;

47 R = N
48 R = N

14

11

42 R = N
43 R = N

InterBioScreen

O
O
O

57 R = BnNH;
58 R = NMe2HCl

54 R = N
55 R = N

O;

56 R = N

52 R = NEt2;
53 R = NMe2;

, Artemisia
glabella Kar. et Kir., 5658 [61].
59 60, Saussurea radix [62].
OH

NH

EtOH, Et3N

1% HCl

OH
O

O
59

60 (76%)


. , [63] 63,
61 62. 62 Pd/C
63.
H

Pd/C, H2

EtOH

NaHCO3, MeI

O
O
61

Me2NH

HO
Me2N

NMe2

O
O

62

, 2

63

15


.
64, Stizolophus balsamita (Lam.) Cass. ex Takht.,
65 66 [64], = 1011
66.
OH
O

OH
O

K2CO3/MeOH

K2CO3/MeOH
pH = 1011

pH = 89

O
O

64

OH

O
O

65 (60%)

OMe

O
O

OH

OMe

66 (70%)

[65] 6768 . ,

69.
+

Na
O
O

O
S H

Cl

Na O
O S
H

O O
67

S
O
+
Na

O
O O
68

N H

S O

Cl

O
O

Na

H N

69

=, .
, 70 CH2N2
71 [6667].
16

InterBioScreen

CH2N2

N
O
70

O
O

71


, 7274, 7576, 7779. ,
31, 73 .

NaP(O)(OR)2

HP(O)(OR)2

OR
P

OR

O
H
O

O
H

O
OR
P OR
O

OR
P

OR

O O

OR

72 R = Me;
73 R = Et;
74 R = Pr

OR

75 R = Me;
76 R = Et

77 R = Me;
78 R = Et;
79 R = Pr

, .
[68] 80 , . :CF2
8185.
F
F

F
O

O
80

O
81

O
82

, 2

17

F
F

O
F

O
83

O
O
85

84

5 KMnO4 -18--6 11,13- 86,


(, 1, 13).

KMnO4

O
H

18--6,

OH
O
O

OH

86

- -
7.
[6970] (7) 7-,
. 8790, 59, . 7,11- . 98100
- 7- 101103.
R

a, b

O
87 R = H, X = CH2;
88 R = Br, X = CH2;
89 R = OH, X = CH2;
90 R = H, X = -OH, -Me

18

Br

O
9194

O
O

95 R = H, X = CH2;
96 R = OH, X = CH2;
97 R = H, X = -OH, -Me

InterBioScreen

R
e

OH

O
X

X
O

98 R = H, X = CH2;
99 R = OH, X = CH2;
100 R = H, X = -OH, -Me

O
O

101 R = H, X = CH2;
102 R = OH, X = CH2;
103 R = H, X = -OH, -Me

a - (), ;
b - LiBr/Li2CO3; c - n-Bu3SnH; d - H2O2/NaOH; e - t-BuOK,


, . [71] (+)-1,2- 105 104 (DIBALH).

O
H

DIBALH

104

105

-
""
1, 107109 109jm [7275]. 2 .
H

O
O
O

O
O
O

R R'
1 R = R' = O;
106 R = H, R' = OH

107

O
O
O
O
108

H
O
O
O
R"
R'

O
OR

109am

, 2

19

2.

R'

R"

,
%

P2O5, CH2Cl2, 25C


BF3, Et2O, 25C, 24
m-CPBA/KF, CH2Cl2,
0C
m-CPBA, CH2Cl2/EtOH,
25C
"

80
85

[72]
[73]

60

[75]

70

[75]

EtOH/TsOH, 22 , 25C
Ph3PHBr, CH2Cl2, 25C

20
23
29

[75]
[74]
[72]

EtOH/TsOH, 22 , 25C
Ph3PHBr, CH2Cl2, 25C

69
9

[74]
[72]

BF3Et2O/ROH, 25,
24
"
"
"
(1) KOH, (2) AcOH
"
"
"

[73]

[73]
[73]
[73]
[73]
[73]
[73]
[73]

107

108

109a

m-COC6H4Cl

OH

CH3

109b
109c

m-COC6H4Cl
Et

CH3
CH3

OH
H

109d

Et

CH3

109e

(R)-CH2CH(CH3)CO2Me

CH3

109f
109g
109h
109j
109k
109l
109m

(S)-CH2CH(CH3)CO2Me
(S)-CH(CH3)CH2CO2Me
(R)-CH(CH3)CH2CO2Me
(R)-CH2CH(CH3)CO2H
(S)-CH2CH(CH3)-CO2H
(S)-CH(CH3)CH2-CO2H
(R)-CH(CH3)CH2-CO2H

CH3
CH3
CH3
CH3
CH3
CH3
CH3

H
H
H
H
H
H
H

[14] 1
.
110, . 111 , 112,
1. , .

H
H

O
O
O O
O

O
O

H
O

O O
O

O
110

20

111

InterBioScreen

O
O O
O

O O
O

112

- KMnO4
[76]. 113,
4,5---,
4,5- .
113 114.
KMnO4

Pb(OAc)4

OH
OH O

O
O

O
113

114

- (m-CPBA) 115
116, b
117, b. 117 [7778].
H
m-CPBA

CHCl3

O
O
115

O
H

O
O

O
116a 10,14;
116b 10,14

117a 10,14;
117b 10,14

- [79].
[80] - ,
. 118 CH2Cl2 MeOH
78C NaBH4 - 119 95%.
, 2

21

OH
O

OMe

O3/CH2Cl2, MeOH
NaBH4

O
H O

H O
118

119

, , -

.
, , .

1.
2.
3.

15.
16.
17.
18.
19.
20.
21.
22.
23.

.., , M.: M, 1978.


Bohlmann F., Natur. Prod. Chem. 1986 65.
Marco J.A., Barbera O., in Studies in Natural Products Chemistry. Structure and
Chemistry (Natural Products from the Genus Artemisia L. Part A), Rahman A., Ed.,
Amsterdam: Elsevier, 1990, p. 201.
Cane D.E., Chem. Rev. 1990 90 1089.
.., . . . 1995 (1) 29.
Fraga B.M., Natur. Prod. Rep. 1999 16 21.
Fraga B.M., Natur. Prod. Rep. 1999 16 711.
Fraga B.M., Natur. Prod. Rep. 2000 17 483.
Hejchman E., Haugwitz R.D., Cushman M., J. Med. Chem. 1995 38 3407.
Takahashi T., Eto H., Yoshioka O., US Patent 4 215 049; . 1981 5233.
Cho J.Y., Park J., Yoo E.S., Planta Medica 1998 64 594.
Beekman A.C., Wierenga P.K., Woerdenbag H.J., et al., Planta Medica 1998
64 7615.
Beekman A.C., Woerdenbag H.J., Uden W.V., et al., J. Nat. Prod. 1997 60 252.
Beekman A.C., Barentsen A.R.W., Woerdenbag H.J., et al., J. Nat. Prod. 1997
60 325.
Adekenov S.M., PCT Int. Appl. WO 9 848 789; Chem. Abstr. 1999 130 480.
Avery M.A., Mehrota S., Johnson T.L., et al., J. Med. Chem. 1996 39 4149.
O'Neil P.M., Bishop L.P., Storr R.C., et al., J. Med. Chem. 1996 39 4511.
Avery M.A., Fan P., Karle J.M., et al., J. Med. Chem. 1996 39 1885.
Avery M.A., Mehrota S., Bonk J.D., et al., J. Med. Chem. 1996 39 2900.
Torok D.S., Ziffer H., Meshnick S.R., et al., J. Med. Chem. 1995 38 5045.
Avery M.A., Bonk J.D., Chong W.K., et al., J. Med. Chem. 1995 38 5038.
4 952 603; . 1991 13238.
593 259; . 2000 19137.

22

InterBioScreen

4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.

24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
59.
60.
61.

0 974 354; . 2000 19138.


0 974 594; . 2000 19139.
0 974 593; . 2000 19140.
Luo X.-D., Shen Ch.-Ch., Med. Res. Rev. 1987 7 29.
Avery M.A., Gao F., Chong W.K.M., et al., J. Med. Chem. 1993 36 4264.
Butler A.R., Wu Y.-L., Chem. Soc. Rev. 1992 85.
Bhattacharya A.K., Sharma R.P., Heterocycles 2000 51 (7) 1681.
Montanaro S., Bardon A., Catalan C.A.N., Fitoterapia 1996 67 (2) 185.
Zheng W.F., Tan R.X., Yang L., Liu Z.L., Spectrosc. Lett. 1996 29 1589.
Ross G., Prawat H., Walter C.U., et al., Planta Med. 1998 64 673.
Passreiter C.M., Sandoval-Ramirez J., Wright C.W., J. Nat. Prod. 1999 62 1093.
Vajs V., Todorovic N., Ristic M., et al., Phytochemistry 1999 52 383.
Ruengeler P., Lyss G., Castro V., et al., Planta Med. 1998 64 588.
Macias F.A., Torres A., Molinillo J.M.G., et al., Phytochemistry 1996 43 1205.
Perez de Luque A., Galindo J.C.G., Macias F.A., Jorrin J., Phytochemistry 2000
53 45.
Daniewski W.M., Gumulka M., Ptaszynska K., et al., Eur. J. Entomol. 1993 90 65.
Szafranski F., Bloszyk E., Drozdz B., Belg. J. Bot. 1991 124 60.
.., .., .. ., . . . ",
", , 1999, . 3, . 54.
Schmidt T.J., Bioorg. Med. Chem. 1997 5 645.
Lee S.H., Kim M.J., Bok S.H., et al., J. Org. Chem. 1998 63 7111.
Lee S.H., Kang H.M., Song H.-Ch., Lee K.B.-M., Tetrahedron 2000 56 (27) 4711.
Shaikenov T.E., Adekenov S.M., US Patent 29 580 328, 1998.
Hewlett M.J., Begley M.J., Groenewegen W.A., et al., J. Chem. Soc. Perkin
Trans. 1 1996 1979.
.., .., .. ., . . . 1999
(1) 71.
Karube A., Maruyama M., Nippon Kagaku Kaishi 1990 (1) 53.
Blay G., Bargues V., Cardona L., Tetrahedron 2001 (57) 9719.
.., .., .. ., . . . 2001
(3) 197.
Blay G., Cardona L., Garcia B., et al., Tetrahedron 1996 52 (31) 10507.
Grieco P.A., Miyashita M., J. Org. Chem. 1974 39 120.
.., .., . . . 1992 (5) 518.
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.., .., .., ..,
. . . 1982 (5) 655.
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Economy Printing, 1997, p. 1.
.., .., .. ., . . . 1999
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.., .., .., .., . .
. 2000 (3) 233.
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.., .., .., . . . 1999 (2) 188.

, 2

23

62. Yoshikawa M., Hatakeyama S., Inoue Y., Yamahara J., Chem. Pharm. Bull. 1993
41 (1) 214.
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Sect. B 1989 28 (7) 543.
64. .., .., .. ., . . . 1991
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65. Hejchman E., Haugwitz R.D., Cushman M., J. Med. Chem. 1995 38 (17) 3407.
66. .., .., ,
-: , 1990.
67. Singh S., Goyal R., Gupta S.K., et al., Indian J. Chem., Sect. B 1993 32 (12) 1229.
68. Salazar I., Diaz E., Tetrahedron 1979 35 815.
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77. .., .., .., .
, . . 1992 (4) 79.
78. .., .., .., . . . 1991
(5) 648.
79. .., . - . , .: , 1992.
80. Watanabe M., Harada N., J. Org. Chem. 1995 60 (22) 7372.

24

InterBioScreen


2-
..
. ..
119991, , ., 47

2- -,
. , , . - ,
: HF, HFBF3 HFSbF5
[14], [25],
. 1 [1], .
,
,
( 1,2-
),
-- [6].
,
, , HCl
( AlCl3 1a 50%
, ,
- 2a).

R' R"

Cl

R'
AlCl3

S
+

H
R'

AlCl4

COR"
1ac

2ac

a R = R' = H; b R = Me, R' = H; c R = R' = Me


HCl AlCl3 [6]
[710], , 2

25

[1113]. -, 2a, 2-- 2b 2,5- 2, 2-()- (2d, R = MeS, R' = H) 2--5-() (2e, R = MeS, R' = Me),
( 1)
( ) [6].
2,5--2- 2c,
3,5--2-
[7].
-
. ,
[1], HF ,
40, HFBF3 - 20,
2,5--2-, HFSbF5,
60. , ,
2- AlCl4; , -
. ,

, - , [14].

[15].
5--2- (2b, fh) 3--2- (3b, fh), 2- 3-
(. 1). AlCl3
,
, .. "" -,
. , , ,
. , ,
, , AlCl3
, [15].

AlkX
AlCl3

Alk

S
+

H
H

S
+

AlCl4
2

H
H

AlCl4
Alk

Alk = Me (b), Et (f); i-Pr (g), t-Bu (h)

26

InterBioScreen

1. 2- 3-, AlCl3

,
2- 3-

MeBr

EtBr

i-PrCl

t-BuCl

10
73 : 27

20
65 : 35

70
60 : 40

70
83 : 17


: 2,4--()
[8] HCl
SnCl4 [16].


- , , , .
2,5-()-2- 2i [6], , 2-()- 2d 2--5-()-2- 2e , ,
40 MeS (, ), 2d.

+
H

H
S
H MeS+

2i

H
H

2d

HCl
-,
.
,
2,4-- ( 50%),
2,5- 2,4- [8].
2,4-() 4,
.

R
S

R
S

RS

R
S

R
S
S
H R

R
S

R
S

S R

, 2

27

R
S

R
S
+
H
S R

R
S

+
H

H
H

S
+

RS

S R
4

.
- . , ,
-
AlCl3 2- 3- 83 : 17
2--, (3%) 3-,
12
[7].
- 2,4---, , , [17] 2,4- 2,5-, ,
, - SnCl4.
( 80), - [9]. 2-- 2--5--
- ,
2--4-- [18].
, ,
1 30 [19].
2,5--2-
5-- 3,5--2- [19]
50 10 [19]. .
Cl

+
H

Cl

Cl

Cl

H
Cl

H
H

Cl

2j

Cl
Cl

S
6

Cl

Cl

S
7

28

Cl

Cl
HCl
+
H

Cl

S
H Cl

Cl
H
H

InterBioScreen

, 2,4--2- 5

2,5--2- 2j.
2,4- 6 2,5-, 3,5,4'-2,2'- 7, , ,
5 6 [10].


2,4- 6 3,5--2- 5, 7, , 5 .
,
. 1950 .
[20],
,
[21].
2-
[22], 5,5'--2,3-.
. ,
[b] AlCl3 TiCl4, , [23],
-, 2,3-[b]

.
,
(. [24])
, "" . , 2- 2- 8 [13] (. 2).
+
H

Cl

H
H

H
H

Ar
Cl

HCl

ArH
+
H

Cl

Ar

, 2

29

2. 2- 2- AlCl3 ( 1 : 1 : 1)

2-
3-
1,3-
1-
2-


2-(4-)
2-(2--4-)
2-(3--4-)
2-(2,4-)
2-(4--1-)
2-(2--1-)

, %
44
51
53
55
83
59

. ,
2- ,
, 2-, 5--2,2'-, 44% [13],
, 2-
, .
2-, , , 2,4- 1-
2-(2,4-) (8,
Ar = 2,4-(MeO)2C6H3) 2-(4--1-) (8, Ar = -(4-MeOC10H6))
55 83% [13].
2,5-
4--2- 9, 4--2-
62% [25] (. 3).
3. 4--2- 2,5- AlCl3 ( 1 : 3 : 1, )

4--2-
4-(4-)-2-
4-(4-)-2-
4-(2,4-)-2-
4-(3,4-)-2-
4-(2-)-2-

, %
62
54
66
63
63
52

, 4--2- 9 2,4- 10 [26].


30

InterBioScreen

, 3--2- 2,4- 10
[27] (. 4).

Ar

+
H

Cl

Cl

H
Cl

Cl

ArH

Cl

Ar

H
H
HCl Cl
Cl

S
9

Ar'H

H
H

Cl

Ar

Ar

Ar

+
H

Ar'
Cl

H
H

HCl Ar'

S
10

Ar
S

HCl

Ar

+
H
+

Cl

Ar'H

H
Cl

Ar

Ar'
H

H
Cl

4. 2,4- 3--2-
AlCl3 ( 1 : 8 : 1, )
3--2-
3--2-
3-(-)-2-
3-(-)-2-
3-(4-)-2-

, %

2-(4-)4-
2-(4-)4-(-)
2-(4-)4-(-)
2,4-(4-)

56
43
46
45


,
. , - [2831].
+
H

H
R

[H ]

, 2

H
H
R

31


[H ]

+
H

(. 5).
,
, , 2- . ,
[28, 29].
- 2- ,
, . .
, ,
, HSiEt3HCl/AlCl3, ..
, [30, 31].
5. CF3COOHHSiEt3 50

:
HSiEt3 :
CF3COOH

1 : 2 : 10

80

2-

1:2:7

20

2,5
3-

1:2:7

20

1:2:9

80

1 : 5 : 20

50

1:4:8

30

1:3:8

50

1 : 7 : 13

50

1:3:9

125

3,4-
1,6-(2-)
2,5---
2,5-(2-)
[b]

32

2-
2,5-
3-
3,4-
1,6-(2-)-
2,5--
2,5-(2-)
2,3-[b]

,
%

15
30
80
80
60
70
70
15
60
55

InterBioScreen

5.
2-[b]
3-[b]
--2
(2-)

1:1:7

20

90

20

2--2,3[b]
3--2,3-[b]

1:1:7

20

1 : 3 : 10

80

1 : 3 : 10

20

50

-(2)
2-
2-
2-

1 : 3 : 10

20

20
50

1 : 4 : 80

30

1 : 5 : 10
1:5:9

50
30

5-(2-)

1:2:7

30

2-
(2-)
2-
2-
5-(-2-)

70

65
55
75
65

, , , , . ,
, ,

.
CS .

,
2- ,
. , -, -- ,
. ,

[32]
- , 8085%.
, ,

[33]. , ,
, 2

33

2- (, ) [34, 35]

[36]. 8090%.

, 2-

, .
, .
2- , .
( 01-03-33150).

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.

20.
21.

Hogeveen H., Recl. Trav. Chim. 1966 85 1072.


Koster P.B., Janssen M.J., J. Chem. Soc. Perkin Trans. 2 1976 (3) 323.
Hart H., Sasaoka M., J. Am. Chem. Soc. 1978 100 4326.
Forsyth D.A., Vogel D.E., J. Org. Chem. 1979 44 3917.
Hogeveen H., Kellog R.M., Kuindersma K.A., Tetrahedron Lett. 1973 (40) 3229.
.., .., .., 1975 11 424.
Belen'kii L.I., Yakubov A.P., Tetrahedron 1984 40 2471.
.., .., .., 1978 14 641.
Belen'kii L.I., Yakubov A.P., Tetrahedron 1986 42 759.
Belen'kii L.I., Gromova G.P., Krayushkin M.M., Gazz. Chim. Ital. 1990 120 365.
Yokoyama Y., Yamashita Y., Takahashi K., Sone T., Chem. Lett. 1981 (6) 813.
Yokoyama Y., Yamashita Y., Takahashi K., Sone T., Bull. Chem. Soc. Jpn. 1983
56 2208.
Sone T., Yokoyama R., Okuyama Y., Sato K., Bull. Chem. Soc. Jpn. 1986 59 83.
.., .., .., .., . ,
C. . 1982 (1) 85.
.., .., .., 1977 13 364.
.., .., .., .., 1979
15 1289.
.., .., .., 1988 (8) 1034.
.., .., .., 1993 (8) 1040.
Yamashita Y., Yoshino O., Takahashi K., Sone T., Magn. Reson. Chem. 1986
24 699.
Meisel S.L., Johnson G.C., Hartough H.D., J. Am. Chem. Soc. 1950 72 1910.
Curtis R.F., Jones D.M., Ferguson G., et al., Chem. Commun. 1969 (4) 165.

34

InterBioScreen

13.
14.
15.
16.
17.
18.
19.

22. Sone T., Kubo M., Kanno T., Chem. Lett. 1982 (8) 1195.
23. Clark P.D., Clarke K., Ewing D.F., Scrowston R.M., J. Chem. Soc. Perkin
Trans. 1 1980 (3) 677.
24. Sone T., Sato K., Bull. Yamagata Univ. 1999 25 (2) 69.
25. Sone T., Inoue M., Sato K., Bull. Chem. Soc. Jpn. 1988 61 3779.
26. Sone T., Sato K., Abstr. 16th Int. Congress of Heterocyclic Chemistry, Bozman,
Montana (USA), 1997, POII-249.
27. Sone T., Sato K., Umetsu Y., et al., Bull. Chem. Soc. Jpn. 1994 67 2187.
28. .., .., .., .., . ,
. . 1973 (8) 1918.
29. Kursanov D.N., Parnes Z.N., Bolestova G.I., Belen'kii L.I., Tetrahedron 1975
31 311.
30. Parnes Z.N., Lyakhovetsky Yu.I., Kalinkin M.I., et al., Tetrahedron 1978 34 1703.
31. .., .., .., ..,
, : , 1979, . 61.
32. , . 2, .: - ,
1949, . 76.
33. .., .., .., 1970 6 2518.
34. .., .., .. ., 2000 (2) 261;
. 2000 (3) 431.
35. .., .., .. ., 2001 (1) 81.
36. .., .., .. ., . , . .
2002 (8) 1392.

, 2

35



..

414000, , . , 1


,
. N-
.

. N- 1ae 1,3-
[1, 2].
N
R

R"
R'

1ae
a R = R' = R'' = CO2Et; b R = CCl3, R' = H, R'' = CO2Et;
c R = CCl3, R' = H, R'' = CO2Me; d R = R' = H, R'' = CO2Et;
e R = R' = CO2Me, R'' = Boc

1 , , 2,3-,
, 1-,
, [1].
1b 1 1,3-
[2]. N-(2,2,2-)- 1b , , 2,3- 1--2--1,2,3,6-
2ac.
O
R'
N
OEt
R

2ac

CCl3

R = R' = H (a); R = Me, R' = H (b); R = R' = Me (c)

36

InterBioScreen

[3] , 1c
(0, ) ~80% 1--2-1,2- 3.

CCl3

+
OR

OMe

CCl3

CCl3
N

OR

OMe

ROH

OMe
O

1c

3
R = Me (a), Et (b)

[4] , 1d -1,3- 2--2-[2,2,2]-5- 4,


5.

O
N

OEt

H
N
[H]

OEt
4

1b
2 : 1. 6a -
.

O
OEt
N
R'
R
6
R = H, R' = CCl3 (a); R = CCl3, R' = H (b)

[5] [6] .
, , -,
-- 1 , -,
, 2

37

n- ,
- .
1,3-
. , 1
7, ""
8 [1].

1a

Ph

Ph

CO2Et

CO2Et
CO2Et

CO2Et
CO2Et
N
R
N
H

CO2Et

1a

R
N
H
8a, b

R = H (a); R = CO2Et (b)

[1] .

1 1e, -
,
: 9.
CO2Me
CO2Me
N
R
N
H

Boc

CO2Me

MeO2C
1e

CO2Me

N
H
9

1ae
,
. , [711], N,N-- N,N- 10
38

InterBioScreen

, N--1,2,3,6- 11.
[11, 12].
OR'
O

NH
R

OR'

N
H

BF3Et2O

+
N
O

O
OR'

H2N

OR'
11

10

, 12, -,
, -N,O- 13, 14 [12].
O

H
OH

R'

CO2Et

R R'

OEt
NH

O
R'

N
H
OH

O
R

13

OEt

R'
O

R
12

HN
R"CH=CH2

OEt

R'
O
R

R"

14

13

. .
2- 15.
, 2

39

OEt

O
H

Ph

HN
OH

OEt

H2N

15

2- 16.
R
OH
R

N
OEt

O
R
16

3- 17 BF3 18, LiAlH4 d,l- 19 [13].


O
HN

OEt
NH

N
17

OEt

LiAlH4

+
N

O
18

OEt

N
N
19

[14] (. [12]).
N,N- -, -, - [15, 16]
, 20 ,
-1,3-. ,
- .
40

InterBioScreen

OEt
O

BF3

NH

+
H

OEt

N
H

O
OEt

H2N

OEt

+
R

( )n
( )n

( )n

+
H

OEt

NH

20

OEt

[17]

.
[18], N,N-
,
1,2,5,6- 5,6--4-1,3-.

N,N- [10].
1,3-
, ,
[3], d,l- d,l-N- [13].
[19]
. , 21 22 23,

1,3- 24.
OEt

HN
O

MeO

O
OEt

BF3Et2O

NH
OEt

21

22

O
N

O
OEt

N
OEt

MeO

O
23

MeO

24

, 2

41

. 11--14-.
, 1,2,5,6-,
,
, - , , .
N--1,2-, N- [20],
[21], [20, 22].
, .
-N-(n-) 1,3- 2l2
25 1,2- [23].
0
3--6--1-(-)-2 [23, 24].
, , N,N'---
1,3-
[25].

[4,1,0]-3-.
O
CH2N2

N2

OMe

OMe

25

N
O

OMe

OMe

O
OMe

R'

R"

20C, 24

R'

R"
OMe

26ac
R'+R'' = CH=CH-CH2 (a), (CH2)4 (b); R' = Ph, R'' = H (c)

42

InterBioScreen

- in situ l3Et2O 0
25 [27]. ,
, c N,N'---

26 [27, 28].
N- N- -N-(-) (-YC6H4XCH2R,
R = CH=CH2) (
)
1,3- 3,5- 27, 28ah, -N- (-YC6H4XCH2R, R = CCH) 29ah [2932].

O N

HN

OH
N

O
O

R'
Y

R'

27, 28

PhSO2NNaCl

O N

EtOH,

R'
Y

29ah

27 X = NHCO2, Y = H; 28 X = O, Y = NHCO2Me; 29 X = NHCO2, Y = H;


R' = H (a), 4-OMe (b), 3,4-OCH2O (c), 4-Cl (d), 4-Br (e), 3-NO2 (f), 4-NO2 (g), 2-OMe (h)

-N- (-N-)
3,5- 2- 30 [33].

O
HN

Ph
HN

Ph

( )n

N
O

R'

O
O

, 5

O
N
R'

n( ) Ph

30ad
a n = 0, R = R' = i-Pr; b n = 0, R = CH2=CHCH2, R' = 4-MeOC6H4;
c n = 0, R = CH2=CHCH2, R' = -;
d n = 1, R = CH2=CHCH2, R' = -611

, 2

43

[3+2]- -N- N- 4,5-5--3-(2--3,1'-)


2-(N-)-7-4,6,7,11--5-([3,2-a][2]-5,1'-) 31, 32 [33].

O
HN

N
O

105C, 5

+
N

N
O

O
O
31

O
NH
Ph

O
32

NH
Ph

-N-(1-)
3--4-[(1-)] [34].

,

, .
N- .
( )
( ).
, , ,
, [35].
44

InterBioScreen

O
HN

Ph
O
NH2

N=C=O

H
N

NH2

N
H

PhOH

, -, [36].

[37, 38].

EtOH

N
Ph

N Ph
H

Cl

EtOH, EtO

O
O
O

+ Ph

HN

Ph
HN

O
O

PhNH2

Br

-N-(3-) 2--1,3 33 [39].


[10],
N-() BF3.

+
Cl

OEt
O

BF3

N
Ph

33

N- 34
1,3--2,4- 35 [40].
, 2

45

OH

O
R

O
O

34

35

[41], [42] (650) 3--2- 36 6-1,3--6- 37.

O
NH

NCO

H
N

H
O

36

37

N- .
[43, 44] - 38 39 40 41 .

MeBr

R"
R'
O

R'"
N R
O

R'"

O R'

O
Br

R"

39

R'"

R
R"

O
Br

KOH
Et2O

R'

N
R'"
R'

R"
40

38
NaOH
H2OEtOH

46

H
N
R'"
R'

R"
41

InterBioScreen

N,N- N-- N,N- ;


-, [45]
N- .

O
Br

N
R

Br H
H

H H

MeBr

HN

NH
O

42a, b
25
43a 43b [46, 47]. [48] ,
42ad AlCl3
-() 44ad, , ,
25 43ad.
O
R

O
R'

O
O

H2N

AlCl3,

OEt

R'

H2N

42ad

44ad

P2O5,

R
N

R'
N

O
43ad

R = H, R' = Bn (a); R = Me, R' = Bn (b);


R = H, R' = i-Pr (c); R = H, R' = Me (d)

45
46 [49, 50].
[5153], N- 45, 1 ,
.
, 2

47

O
HN

O
O

OH

, .
O
45

46

[54] N- 2- 47,
, , -(). , N- 48af, , ,

, , ,
.

O
R'

OMe
NH

R'

HO

NH
O

OMe

R'

H
N

R'

N
H

R"
N

KOH/K2CO3
R'
TEBAC
R"X

O
N
R"

R'

47

48af

R' = H, R'' = Bn (a); R' = H, R'' = Me (b); R' = H, R'' = Et (c);


R' = H, R'' = sec-Bu (d); R' = Me, R'' = Bn (e); R' = Me, R'' = Bu (f)

[12]
N- , .
[55] [2,2]-4,5,12,13 49 N- ,
50ae.

O
O
O

O
49

48

HN

OEt

2
R

InterBioScreen

O
O
R

O
50ae
a R = MeO; b R = Me; c R = Ph; d R = NO2; e R = Cl

-N-(n-) -N-(2--4-) 6--1--1,2--4H-3,1- 51, 10%


( l ~43% ) 25% ( l ~37%) [56].

O
O

HN

O
N

H2CO + HCl

, 20C
51

[57] -N-[2-(1--2-Y-)] (52, Y = SMe, SOMe, SO2Me)


N- 53, 54.

O
O

NH

Y
OH

Y
K2CO3

Y = SMe

53 H

52
Br2

O
O

NH

Br
HO OH
OH

TsOH

NaH

N
O

OEt

OEt

54

, 2

49

55 -2- 56 [58, 59].

O
O

NH
N

N
HCl

H2N

H2N

R
N

55

56

N-[2-(2-)]- N-[1-(2-)-2-] 3--4--3,4--2-1,3-2- 57ae 2--1--2,3--1-[1,2-e][1,3]-3- 58 [60].

NO2

NO2
R"

N
O

Ar

N
O

Ar
O

R'
58a, b

57ae

57: R' = R'' = H, Ar = Ph (a), R' = R'' = H, Ar = p-ClC6H4 (b),


R' = H, R'' = Cl, Ar = Ph (c), R' = H, R'' = Cl, Ar = p-ClC6H4 (d),
R' = H, R'' = Br, Ar = Ph (e);
58: Ar = Ph (a), p-ClC6H4 (b)

N- - - 59
[12, 6163] 2- 60 N--2--1,3- 61.

O
n=2

O
O

HN
Ar
59

Hal
( )n

N Ar

HO

60

O
n=3

Ar

61
Hal = Cl, Br; Ar = Ph, 3,4-ClC6H3

50

InterBioScreen


Na 6,6- 3--1,3--2- 63,

62 [64].

Ar
N
R

O
R'

H
N
Ar

62a, b

O
O

R R'
63a, b

a R = Me, R' = Et; b R+R' = (CH2)5

, N-
4--3--2- 64 [65].
O
R

Ph

O
R'

N
H

Ph N

O
R'
64

4--2--1-
N- 65ac,
2- , Py, KOH, MeONa
[66]. 65
(. [65]) . , ,

, .
13 65 [66] [67, 68], R'2NCH2 .
66 , (2)
( = 12.6), .
, 66 MeONa 1825
5,5--4-()3--2- 67.
13 , , , [69].
, 2

51

Ph

HN

NH

R'

MeI

R'

Ph

N R'
R'

65ac

66ac

R'
+
R' N

R
O

N
Ph

67c
a R = H, R' = Me; b R = H, R' = Et; c R = R' = Me

[70], 3--1,2- N-(2-)-3--2- 68 N-(3--2-)-2- 69, ..


NH . 69 NaOH 70 [71].

OH
Cl

O
O

Cl

O
NH

OH
O

N
O

68

NaOH

69

O
O

O
O
70

[72] N-(-) 71
70,
6-R- 72 .
52

InterBioScreen

O
NH
N +
N
N

H
N

NaH/

O
N
H

71ac

72ac

a R = H; b R = Cl; c R = Me

. [73] , 2-()-1- 73 1,2,4-[2,3-a]-2- 74.

O
EtO

NH

+ O

N O

74

73

[74] , 2-()1- 1-()-2-


.
N- [75].
- [7678].
N- 75 , 120 4 (-4,4'(1)-)-2,2',5(3) 76 [79, 80],
2-
N-.
H
N

O
O
N
O

OEt

H2N

HN

NH2

O
OH
NH

OEt

75

, 2

53

H
N

O
HN

RNH2
EtOH

O
NR
N
H

76
R = H (59%), NH2 (57%), OH (15%)

1,3--2- 78
N- 77, 1,3--2- [8183].
H
N

NH2
O
NH

NH
O

N
H

OPh
78

77

,
-N-(o-), -
, [84].
-, , -
, - TMSCCH
Pd .

OEt
NH

EtONa

R
N

R
R = SiMe3, Bu, Ph

OEt

H2O

R
N
H
R = H, Bu, Ph

[85] 7- 80
6- --2-() 79 .
54

InterBioScreen

SiMe3

SiMe3

NHBoc

t-BuLi (2.2 .)
Et2O, 20C, 3
E+

NHBoc

t-BuOK
t-BuOH

N
H

E
79

80

E = Br, I, Me2C=CHCH2, PhCO

[8688] , (OMe -O-Si(i-Pr)3)


. , , .

SiMe3
I
NHBoc

SiMe3

RO

Pd(PPh3)2Cl2
CuI, Et3N, 20C

t-BuOK
t-BuOH

NHBoc
RO

RO
N
H

R = 4-Me (70%), 7-Me (70%), 5-Me (79%), 6-Si(i-Pr)3 (67%),


7-Si(i-Pr)3 (10%), 5-Si(i-Pr)3 (70%)


( , , .)
[8991]. , --N 81 , -
82, 83 1,3- 84,
.
, 2

55

H
N

PhCN

O
N

2 , 20C
1 , 20C

Ph
82 (83%)

Li
O

O
N

PhN=C=O

Li

2 , 20C
1 , 20C

H
N

O
N

Ph

81

83 (57%)

H
N

p-ClC6H4CHO

O
O

2.5 , 20C

C6H4Cl- p
84 (35%)

- --N- 81 85 ,
, . 81
85 86 [92].

ClO4
Me2N

R'

NMe2

R
2 t-BuLi

R'

Li

HN

85

R'

N
O

H2O

N
OLi

OLi

O
81

56

InterBioScreen

H
R

O
R'

O
R'

N
Me2NH

NH

NH
Boc

Boc

N
R'

R
N

R'

Boc

+
H

OH

R'
N

OH

Boc

86

R = R' = H (a); R = H, R' = F (b); R = H, R' = Cl (c); R = H, R' = Me (d);


R = H, R' = OMe (e); R = Ph, R' = F (f); R = Ph, R' = Cl (g); R = Ph, R' = Me (h);
R = Ph, R' = OMe (i); R = Me, R' = H (k)

N-, - , --N-. ,
,
.
[93] 3--5---4--2- 88, 89
-N- 1--3,3--2- 87
1--3--3--2- 87b 2.2 . LiN(TMS)2
20. .
O
Br
87a

O
HN
R

N
OEt
LiN(TMS)2

R'

R'
87b

88

O
R'

Br

N
R
89

R'
O

, 2

57

N-(-) N-(-)-1,2,3,4- 90 -
1--3- [94].

Boc
H
N
R

2.5 . t-BuLi,

Cl ,

R
90

4-(-) 1,2,3,4--1,6- 91.

Boc
N
N
91 (28%)

[95] 92a, b -1,3- [1,2-a] 93a, b.


, .

X
O
X

H2/Pd/C

NH

NaH/

OH
N

P2S5
Ni

92a, b

X
N
93a, b
X = HNTs (a), HNSO2NMe2 (b)

58

InterBioScreen

N,N'--- - - 20
MeONa 94,
22%-
95 [96, 97].

O
HN

OMe
O

HCl

R
O

NH

R'

R'

H
N

MeO
O

R
N
O

OMe

OMe
94ag

95ag

R = Me, R' = COMe (a); R = Me, R' = COPh (b); R = R' = CH2Ce2CH2CO (c);
R = Me, R' = CO2Et (d); R = Ph, R' = CO2Et (e); R = Me, R' = Ts (f); R = Ph, R' = Ts (g)

, ,

.

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.

Vor der Brck D., Bhler R., Plieninger H., Tetrahedron 1972 (28) 791.
Imagawa T., Sisido K., Kawanisi M., Bull. Chem. Soc. Jpn. 1973 46 2922.
.., .., .., 1980 (2) 273.
Cava M.P., Wilkins C.K., Chem. Ind. (London) 1964 1422.
.., .., .., .., 1974
10 1164.
Biehler G.-M., Fleury G.-P., Perchai S.I., Regent A., Tetrahedron Lett. 1968 4227.
Merten R., Belg. Patent 618 455; Chem. Abstr. 1963 58 9033g.
Merten R., Belg. Patent 611 643; Chem. Abstr. 1962 57 16373b.
Merten R., Belg. Patent 608 904; Chem. Abstr. 1963 59 2781d.
Merten R., Mller G., Angew. Chem. 1962 74 866.
Merten R., Mller G., Chem. Ber. 1964 97 682.
Adams R., Baron F.A., Chem. Rev. 1965 65 567.
Quan P.M., Kains T.K.B., Quin L.D., Chem. Ind. (London) 1964 1553.
Sen R.N., Mukherji A., J. Indian Chem. Soc. 1930 7 275; Chem. Abstr. 1930
24 4779.
Krow G., Rodebaugh R., Carmosin R., et al., J. Am. Chem. Soc. 1973 95 5273.

, 2

59

16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
49.

60

Krow G., Rodebaugh R., Grippi M., et al., J. Org. Chem. 1973 38 3094.
Sasaki T., Fguchi S., Sugimoto M., Hibi F., J. Org. Chem. 1972 37 2317.
Giordano C., Abis L., Gazz. Chim. Ital. 1974 104 1181.
Huisman H.O., Angew. Chem. 1971 83 511.
Fowler F.W., J. Org. Chem. 1972 37 (9) 1321.
Fraenkel G., Cooper J.W., Fink C.M., Angew. Chem. 1970 82 518.
.., .., 1983 19 123.
.., 2000 36 1242.
Kresze G., Shulz G., Firl F., Angew. Chem. Int. Ed. 1963 2 (5) 263.
.., .., .., ..,
. , . . . 1994 37 (1012) 23.
Hisano T., Yoshikawa S., Muraoka K., Chem. Pharm. Bull. 1974 22 (7) 1611.
Velikorodov A.V., Mochalin V.B., Abstr. 4th Int. Symp. Mod. Probl. of Aliphatic
Diazo Compounds Chemistry, Saint-Petersburg (Russia), 2000, p. 37.
.., .., 2002, .
.., .., 2001 37 (1) 93.
.., .., .
, : . 1 . . ., ,
2001, . 13.
.., .., .., .
, . .., .., .: -,
2001, . 2, . 62.
.., .., .., . , . .
. 2001 44 (6) 22.
.., .., .., . 7 . -.
. " 2001", :
. . -, 2001, c. 112.
.., .., .., .., .-.
. 1998 22 (4) 431.
Hegarty A.F., Frost L.N., J. Chem. Soc. Perkin Trans. 2 1973 (13) 1249.
Carpino L.A., Parameswaran K.N., Kirkley R.K., et al., J. Org. Chem. 1970 35
(10) 3291.
Scott F.L., Fenton D.F., Tetrahedron Lett. 1970 (9) 681.
Farrissey M.J., Nasky A.M., J. Heterocycl. Chem. 1970 7 (2) 331.
Schmidt K., Ger. Patent 1 257 147; Chem. Abstr. 1968 69 10447.
Warrener R.N., Cain F.N., Tetrahedron Lett. 1966 3231.
Meier G., Angew. Chem. Int. Ed. 1974 13 425.
Krantz A., Hoppe B., J. Am. Chem. Soc. 1975 97 6590.
.., .., 1979 (12) 1628.
.., .., 1979 15 (3) 475.
.., . . . . , ., 1979.
Bhattacharya P., Sarkar M., Roychoudhury T., Chakraborty D.P., Chem. Ind.
(London) 1978 532.
Sarkar M., Chakraborty D.P., Phytochemistry 1979 18 694.
Chakraborty P., Mandal A.K., Roy S.K., Synthesis 1981 (12) 977.
.., .., .., . 29.07.80,
4044-80.
InterBioScreen

50. .., .., .., .., . ,


. . . 1978 (8) 1220.
51. .., .., .., .., . .
. 1990 56 (1) 17.
52. .., .., . , . . . 1981 (5) 561.
53. .., .., .., .
, : . . -, 1987, . 60.
54. Julia S., Ginebreda A., Bernabe M.L., Grau M., Afinidad 1982 (39) 275.
55. Nourad A.E., Nour-El-Din A.M., J. Prakt. Chem. 1983 325 (11) 2616.
56. .., . , . . . 1998 41 (2) 98.
57. Garcia Ruano J.L., Pedregal C., Rodrigues J.H., Tetrahedron 1989 45 (3) 203.
58. Slouka J., Nalep K., Z. Chem. 1986 26 (4) 134.
59. Slouka J., Bekrek V., Collect. Czech. Chem. Commun. 1980 45 1379.
60. Latif N., Mishriky N., Assad F.M., Austr. J. Chem. 1982 35 1037.
61. Dox A.W., Yoder L., J. Am. Chem. Soc. 1923 45 723.
62. Pierce J.S., Adams R., J. Am. Chem. Soc. 1923 45 790.
63. Stoffel P.J., Speziale A.J., J. Org. Chem. 1962 27 3079.
64. Shapiro S.L., Bandurco V., Freedman L., J. Org. Chem. 1961 26 3710.
65. Frances T., Thorne M.P., Can. J. Chem. 1976 54 24.
66. .., .., .., ..,
1981 17 (3) 649.
67. Rosenberg D., Drenth W., Tetrahedron 1971 27 3893.
68. .., .., ., 1979 15 254.
69. .., .., .., . .
, , 1978, . 8, 2, . 15.
70. .., .., .., .., 1986
22 (6) 1333.
71. .., .., .. ., 1988 24 (7) 1382.
72. Smalley R.K., Stocker A.W., Tetrahedron Lett. 1984 25 (13) 1389.
73. Katritzky A.R., J. Chem. Soc. 1956 2063.
74. Tanida H., Yakugaku Zasshi 1959 79 (8) 1063.
75. Stoffe P.J., J. Org. Chem. 1964 (28) 2796.
76. Boulton A.G., Ghosh P.B., Katritzky A.R., J. Chem. Soc. B 1966 (11) 1004.
77. Hobin T.P., Tetrahedron 1968 24 6145.
78. .., .., .., .
, .: , 1996.
79. .., .., .., 1998 67 (4) 333.
80. Yamagishi M., Yamada Y., Ozaki K., et al., J. Med. Chem. 1992 35 (11) 2085.
81. Hilse A., Hilse U., Dissertation, Potsdam, 1985.
82. Kempter G., Spindler J., Z. Chem. 1989 29 (8) 276.
83. Kempter G., Ehrlichmann W., Grnert K., et al., Wiss. Z. Pd. Hochschule Potsdam
1980 24 19.
84. Sakamoto T., Kondo Y., Yamanaka H., Heterocycles 1986 (24) 31.
85. Kondo Y., Kojima S., Sakamoto T., eterocycles 1996 43 (12) 2741.
86. Sakamoto T., Kondo Y., Iwashita S., Yamanaka H., Chem. Pharm. Bull. 1987 35
(5) 1823.
87. Sakamoto T., Kondo Y., Iwashita S., et al., Chem. Pharm. Bull. 1988 36 (4) 1305.
, 2

61

88.
89.
90.
91.
92.
93.
94.
95.
96.
97.

62

Kondo Y., Kojima S., Sakamoto T., J. Org. Chem. 1997 62 6507.
Muchowski J.M., Venuti M.C., J. Org. Chem. 1980 45 (23) 4798.
Stanetty P., Koller H., Mihovilovic M., J. Org. Chem. 1992 57 (25) 6833.
Cho I.-S., Grong L., Muchowski J.M., J. Org. Chem. 1991 56 (26) 7288.
Reuter D.C., Flippin L.A., McIntosh J., et al., Tetrahedron Lett. 1994 35
(28) 4899.
Kudo N., Taniguchi M., Sato K., Chem. Pharm. Bull. 1996 44 (4) 699.
Reed J.N., Rotchford J., Strickland D., Tetrahedron Lett. 1988 29 (45) 5725.
Ohnuma T., Sekine Y., Ban Y., Tetrahedron Lett. 1979 27 2533.
.., .., 1998 34 (10) 1555.
.., .., 2001 37 (7) 1100.

InterBioScreen



..
. ..

480100, , , . . , 106

, , , ,
, -,
- ,
[16].
, .. , ,
20 . .

[7] , ,,','-
PdCl2, 1, 2 ( 1).
1

HN

CO

MeOH

H
N

H
N
O

OMe
1

OMe

PdCl2
(/2 = 90 : 10) 1 2 3 4. Pd0/C KI
(/2 = 94 : 6), 5 [8] ( 2).
, 2

63

HN

CO

MeOH

H
N

H
N

MeO

H
N

OMe

O
MeO

OMe

MeO

O O

OMe

PdCl2 -, N-, [8].



/ 4 Pd0/C
KI 3,4-()
6,
7 -3,4- 8 [9] ( 3).
3
R
N
ii

R
N

R
N

R'O

H
N

O
R'O

OR'
6 (1795%)
iv

R = COPh O
(66%)

R = Alk, Ar, AlkOCO, Ts; R' = Alk;


i - CO/, R''OH, Pd/C, KI;
HO
ii - MeCN/Et3N, 2570C, 370 ;
iii - R''OH, Et3N, 2580, 570 ;
iv - (1) Ba(OH)2/H2O, 100C, 15 , (2) H2SO4/H2O;
v - (1) NaOH/H2O, 100C, 3040 , (2) H2SO4/H2O, 0C

64

R'O
iii

OR'
O

7 (1585%)

(27-81%)

OR'
H
N
O

8 (80%)

OH

InterBioScreen

[10], 1,6- 9 Pd0 1012 ( 4).



. 11 10. - (
X = NH, NMe, R = Alk) 10
12.
4

R
R

O
R

R
X R

X
O

+ CO +

11

MeOH
R

R
OR'

R'OH

R
X R

10

R = H, Alk; X = NH, O

12

, "'' 10, 1315 [11] ( 5).


5
Y

R
X R

CO

X
R

13

Q 180250C R
O
X
CO
Z
R

Y
Q
14

Q=H

R
9

R
Y
O
Z

X
R

CO

R
Y

X
R

Z
R

15

X = NH, NCO2Me, NCOPh, O; Y = Ph, CO2Me, H, CN,CH=CH2;


Z = H, Me, CO2Me; Q = H, Me, CO2Me

, 2

65

Pd0/C (10%), Pd0,


Pd2(dba)3 (dba ) Pd,
.
, . 13
15 ( 98%) .
.
Ni Co 9 [12].
,
N,N- PdCl2
CuCl2 AcONa N-
16 -1--5--1,2,5,6--3,4- 17 [13, 14] ( 6).
6

OMe

MeO

xC6H4N

xC6H4N

O
O
xC6H4N

OMe

O
O

OMe
16

OMe
17

17 X = H (11%), p-Cl (36%), m-Cl (40%), m-Br (47%), o-Cl (24%), o-Br (45%)
i - CO, MeOH, 10 . % PdCl2, 4 . CuCl2, 1 . AcONa 1 .

17
16, . 17 16 ( X = p-CH3, p-OCH3 p-Br
17 ) -,
16
PdCl2 [14].
[15, 16], / 18a, b - 19
20, 21 ( 7)
(. 1).
66

InterBioScreen

NTs

NTs

CO
MeOH

M0Ln

AcOH
CH2N2

X
MIILm
18a X = I;
18b X = OAc

O
MeO

NTs

NTs

NTs

MeO
19

20

21

1. (0) (0) / 18a, b

18a
18a
18b


(, )

Ni(CO)3PPh3
Ni(COD)2/dppb
Pd(dba)2/PPh3

, %

A (20)
A (12)
B (2)

19

20

21

69
23
13

57 (20 : 1)
50 (7 : 1)

16

A: 25 . % Ni(0), THF/MeOH 4 : 1, CO (1 ) . .;
B: 10 . % Pd(0), HOAc, CO (1 ), 45


- 22
- 24 -2--3- 23
-2--3- 25 [17] ( 8).

O
i

NH2

22

OMe
Bu

N
H

Bu
23

, 2

67

OMe

Bu
O

Bu

OH
24

25 (66%)
i - CO, MeOH, NaOH, PdCl2, CuCl2

,
Pd, ,
Pd0. Pd0
Pd2+ CuCl2 [17].
, 2- 3- 26. 2- 27 [18] ( 9).
9

CO

MeOH

R
X

XH

26 (1979%)

X = NSO2Me, NH, O;
R = Ph, Bu, CO2Et

R
H
N

OMe

CO

MeOH

R'

OMe
N R'
O

27 (2555%)

R = Ph, Bu; R' = H, Me


i - PdCl2, CuCl2, AcONa ( K2CO3), 3 , 20


--- 28 ,-
, - 29
[19] ( 10).
68

InterBioScreen

10

R'

N
H

N R'
MeO
O

28

OMe

R
N

29

R'

R = Me, Et; R' = Alk, H, COPh, COAlk


i - CO/, Pd0/C, KI, MeOH

, PdI2 Pd0/C KI,



30a, b [20] ( 11).
31 ( 12).
11

R
R'

IPd
R

R'

R'

NH
CO2

R'
R'

PdI2

R
N

R'

HI

CO,
R"OH

R'
R'

HI,
Pd

OR"
O

KI

O
R
R'

R'
R'

O
R'

IPd

PdI

R
N

R
N

CO,
R"OH

HI,
Pd

R'
R'
O

OR"

30a

R
N

O
30b

PdI2
2 HI
Pd

+
+

1/2 O2
I2

H2O

I2

PdI2

, 2

69

12
R'
R'

N
H

R'
R'

PdI2KI

CO2

R
N

O
31

---

, - [21, 22]. , ,
[21],
[22].
,
--- 32 [23] ( 13).
13

O
Ni(CO)4

OH

AcOH/H2O, 80C

32 (23%)

[24, 25] - 33
, ( 14).
14

OH

+
R'

CO

O
R

R'

33 ( 100%)
R, R' = H, (CH2)2Br, (CH2)2CH=CH;
R+R' = (CH2)3, (CH2)4, (CH2)5;
i - PdCl2 (0.07 .), SnCl2 (0.07 .), PPh3 ( PBu3) (0.14 .),
CO ( 7.8 ), MeCN, 6575C

70

InterBioScreen

,
PdCl2, SnCl2 2 .
. - -, - -,
- , (0.11 ), . ,
Pd(II), CO
, -
PdC CC. ,
[25, 26] ( 15).
15

Pd(II)

CO

OH

OPd
Pd(II)
O
O
Pd

+
H

O
O

Pd(II)

O
OH

Pd

OH
- ,
, Pd(II). [26]
SnCl2, .
PdI2/Bu3P/MeCN , ,
, (PdCl2/2Ph3P/SnCl2/MeCN)
( k) , ( 16).
, 2

71

16
+

[PdL2(SnCl3)] Cl

RCCCH2CH2OH
CO

[L2Pd(SnCl3)(RCCCH2CH2OH)] Cl

HCl

[L2Pd(SnCl3)(RCCCH2CH2OH)(CO)] Cl
[L2Pd(SnCl3)(RCCCH2CH2OC(O)]
L2(Cl3Sn)Pd
HCl

[PdL2(SnCl3)] Cl

L = PPh3

, , PdCl2(PPh3)2
(), 2
3(2)- 34.
, CO2 ,
34 [27] ( 17).
17
OH

CO

PhHal

.
CO2,
Et3N

O
OH
R

O
O

R
O
O
O

CO2

O
R

34
R = Ph, 4-MeC6H4, 4-ClC6H4, (E)-PhCH=CH, 1-


5--2(5)- [28, 29].
-2(5)- 35 36 ,
100
100 , [30]
72

InterBioScreen

( 18). 35 36
.
18

O
R

R'

H2O, CO
Rh .,
, Et3N

R'

O
R

35

O
36

R'

, Rh4(CO)12 Rh6(CO)16,
.
,
.
, . , .
.. .

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.

.., ,
.: , 1978.
.., .., , .: , 1987.
Falbe J., New Synthesis with Carbon Monoxide, Berlin: Springer, 1980.
.., .., .., 1988 57 (9) 529.
.., .., 1989 58 (2) 197.
Ojima I., Chem. Rev. 1988 88 1011.
Chiusoli G.P., Costa M., Masarati E., Salerno G., J. Org. Chem. 1983 55 35.
Chiusoli G.P., Costa M., Pergreffi P., et al., Gazz. Chim. Ital. 1985 115 691.
Chiusoli G.P., Costa M., Reverberi S., Synthesis 1989 (4) 262.
Chiusoli G.P., Costa M., Gerbella M., Salerno G.J., Gazz. Chim. Ital. 1985 115 697.
Chiusoli G.P., Costa M., Reverberi S., Salerno G.J., Gazz. Chim. Ital. 1987 117 695.
Chiusoli G.P., Pallini L., Terenghi M.G., Transition Met. Chem. 1983 8 189.
.., .., .., .., 1992
28 (1) 175.
Vizer S.A., Yerzhanov K.B., Manchuk Z.N., Wieser A.G., Eurasian Chem. Tech. J.
1999 1 (1) 1.
Oppolzer W., Bedoya-Zurita M., Switzer C.Y., Tetrahedron Lett. 1988 29 6433.

, 2

73

16. Oppolzer W., Keller T.H., Bedoya-Zurita M., Stone C., Tetrahedron Lett. 1989
30 (43) 5883.
17. Kondo Y., Sakamoto T., Yamanaka M., Heterocycles 1989 29 (6) 1013.
18. Kondo Y., Shiga F., Murata N., et al., Tetrahedron 1994 50 (41) 11803.
19. Bonardi A., Costa M., Gabriele B., et al., Tetrahedron Lett. 1995 36 (41) 7495.
20. Bacchi A., Chiusoli G.P., Costa M., et al., J. Chem. Soc. Chem. Commun. 1997
(13) 1209.
21. Kupehan S.M., Eakin M.A., Thomas A.M., J. Med. Chem. 1971 14 1147.
22. Mc Phail A.T., Onan K.D., Lee K.-H., et al., Tetrahedron Lett. 1974 2739.
23. Jones E.R.H., Shen T.Y., Whiting M.C., J. Chem. Soc. 1950 230.
24. Norton J.R., Shenton K.E., Schwartz J., Tetrahedron Lett. 1975 51.
25. Murray T.F., Samsel E.G., Varma V., Norton J.R., J. Am. Chem. Soc. 1981 103
(25) 7520.
26. Murray T.F., Norton J.R., J. Am. Chem. Soc. 1979 101 4107.
27. Inoue Y., Ohuchi K., Yen I.F., Imaizumi S., Bull. Chem. Soc. Jpn. 1989 62
(11) 3518.
28. Hong P., Mice T., Yamazaki H., Chem. Lett. 1981 989.
29. Mice T., Hong P., Yamazaki H., Chem. Lett. 1981 993.
30. Doyama K., Joh T., Onitzuka K., et al., J. Chem. Soc. Chem. Commun. 1987 649.

74

InterBioScreen




.., ..
. ..

480100, , , . . , 106

, , [14],
[5, 6].
- , 30 , ,
.
1 2
VIII 4 . 3 [7] ( 1).
1
1

R
N

R
6

R
R3

Pd/C, H2

A
R

R1
2
N R 3
R

Pt Ni, H2

HClO4
4

6
R R

2
4

R3

N ( )n N
R R6

R1
2
N R 3
R

R
1

R
R

R3

R3

R4

R6

( )n

3
A =
R1 = H, Alk, AlkO, AlkNR, ; R2, R3, R6, R7 = H, Alk;
R2 +R3 = (CH2)n; R6+R7 = (CH2)n; R4, R5 = H, Alk

, 2

75

4 [8] ( 2).
2

R
R
R

NH

NiL4

HN

R
NH

4 (68%)

5 [9]
( 3).
3

R'
R
R

NH

R''

R''

NiL4

R'''


R'''
MeCN

R'

R'
NH

R'

R = R' = Me; R+R' = (CH2)5; R'' = CMe2NH2, CMe2OH, Ph; R''' = H, Ph;
L = PhP(OPr-i)2, P(OPr-i)3, P(OPh)3

(
) N--- 6ad 7ac,
8, N- - 9ac 10a, b; 11.
- . 8 11
6d 9c [10] ( 4).
R"
i

6ad

N
R'

R'

7ac (4060%)

R"

ii
R = H, R' = Ac,
R" = CH2N

N
Ac

8 (30%)

a R = R" = H, R' = Ac; b R = CO2Et, R' = Ac, R" = H;


c R = H, R' = Ac, R" = Me; d R = H, R' = Ac, R" = CH2N

76

InterBioScreen

R'
i

N
O

10a, b O

N
R'

9ac

ii

N
R = Me, R' = CH2N

11 (33%)
a R = Me, R' = H; b R = Bn, R' = Me; c R = Me, R' = CH2N

i - 10 .% Pd(OAc)2, 20 .% PPh3, MeCN, 4 HN


,
3 HCO2H, 60, 12 ;
ii - 10 .% Pd(OAc)2, 20 .% PPh3, 1 HCO2H, 60, 12

Pd(OAc)2 - 12 15 - 14, 16, 17.


13, -, , .
16 , 17 [11] ( 5).
5

CO2Me

MeO2C
I
N
Ac
12

CO2Me

CO2Me

XPd

MeO2C

CO2Me

N
Ac
13

N
Ac
14 (4065%)

, 2

77

CO2Me

CO2Me

MeO2C

CO2Me

CO2Me

MeO2C
I

ii

N
Ac

N
Ac

17 (6%)

16 (26%)

15

N
Ac

i - 10 .% Pd(OAc)2, 20 .% PPh3, 1 Et4NCl, 1.2 Bu3SnCH=CH2,


MeCN, 25C, 2 , ( HCO2Na, , 70C, 1);
ii - 10 .% Pd(OAc)2, 20 .% PPh3, 1 Et4NCl, MeCN, 70C, 1

--- 18ac N-
CPd Pd(II) : -, [12] ( 6).
6

R'
O
R

PdX2

R"

R'

PdX

O
R

PdX
N

R'

N
R

18a

R" = CHO

R'

O
R

R" = H, Alk, Ar

R"

R"

, -
R" = CH2Y

R'

X
X

R'

H
N

R
18b

18c


()- ()- [12].
78

InterBioScreen

HO

Ph

Ph

N
N

N
N

N
H

()-

()-

3--2,5- 19
.
[13]
( 7).
7

2.5 .% . A

, 80C

19
R = Ph (77%);
R = CH2CHMe2 (65%)

Cl

Ph

PF6

Ru
Ph

CyR

A (Cy = )


-, 20, 21 [14].

20

F3C CO2Me
PG N
21

- 22ac - , -(Cy3P)2Cl2Ru=CHPh [15]


( 8).
, 2

79

X ( )
n

10 .% .

X
( )n

CH2Cl2

22a (70100%)

X = CH2, n = 0, 1;
X = O, n = 1;
X = NTs, n = 1

OSiMe2Bu- t

OSiMe2Bu- t
10 .% .

CH2Cl2

N
R

22b (72100%)

R
R = Me, CH2OSiMe2Bu-t

R
O

10 .% .

CH2Cl2

N
22c (7482%)

R = H, OSiMe2Bu-t

Pd- 23a, b [16] ( 9).


9

Pd(OAc)2/PPh3

N
Ts
R = H, Ph

80

CO2Me

, 70C

R
N
Ts

CO2Me

23a (60%)

InterBioScreen

Pd2(dba)3/PPh3

N
Ts

CO2Me

AcOH, EtSiH
, 100C

N
Ts

CO2Me

23b (50%)

-
. , 3--1- 24
(A) , 25, (B) 26, 25 [17] ( 10).
10
( )5

HO
( )5

A B

HO

( )3 ( )5

25
A: 60%
B:

24

26
30%
>95%

A - PdCl2(PhCN)2 (0.010.03 .), . Et2O, . -, 510 ;


B - PdCl2 (0.010.05 ), . MeCN, 30

27, D [18] ( 11).


11

HO

OTBS

PdCl2(PhCN)2
MeCN, 60C

O
O

O
O

27 (91%)

5--1- 28 29 30 B ( ) [17] ( 12).


, 2

81

12
HO
( )4

A B

( )4

+
( )5

HO

29
A: 50%
B:

28

( )4 ( )5
30
45%
>95%

24 28, 4--1- 31
6-- ,
5-- 1--4- 32 ( 13).
13

HO
( )3

A B

( )5

29

30

HO

( )3 ( )6
32

31
A: 50%
B:

>95%

45%


33, 34
35, 36, -
[17] ( 14).
14
R"

HO
( )n

HO
R'

O
O ( )n+1
R"

R"

R'
33

HO
( )n

OH
( )m

A B

O ( )n+1
O ( )m

O
O ( )n
R'
34

O ( )n
O ( )m+1

35
36
90% (m = 2, n = 3)
A:
95% (m = 2, n = 3)
B:
B: 60% (m = 3, n = 4)
A - PdCl2(PhCN)2 (0.01 .) , ~20, 5;
B - PdCl2 (0.01 .) . MeCN, 1

82

InterBioScreen

- 37 39 :
- 38, -
40 [17] ( 15).
15
R
R

OH

O
37

38 (90%)

OH

O
39

40 (47%)

R = n-Bu

HgCl2, Hg(OAc)2, Hg(OCOCF3)2 - 37


41, - 39 40,
.
N- (NXS), -
42 43 [19] ( 16).
16
O

Hg(II)

37

Et3N
CH2Cl2

Hg(II)
NXS, DMAP
CH2Cl2

X
42 (8793%)

41

X = Br, I, Cl

R = H, n-Bu
Hg(II)

40
(86%)

Et3N

37

(CF3CO2)2Hg
LiI, NXS

Et3N

R
X

43 (7982%)
X = Br, I, Cl

, 2

83

Pd(OAc)2 PdCl2 - 2-HOC6H4CH2C=CH,


HO(CH2)3C=CH , PhI, 2-,
-. , -4-
2- 44 [20] ( 17).
17
Ph

BuLi,
Pd(OAc)2PPh3
PhI

HO

O
44

PdCl2 -
- [17] ( 18).
18
( )5
N
n=2

( )6

H2N
( )n

( )5

N
n=3

(43%)

(63%)

Pd(0) n - - [21] ( 19).


19

Pd(0)

N
Ts

(64%)
R = CO2Me

K2CO3,
<60C
n=1

( )n
HN
Ts

Pd(0)

K2CO3,
60C
n=2

N
Ts

(5887%)
R = CO2Me, CH2OH,
CH2OTBS

Pd(0) -
[22, 23] ( 20).
84

InterBioScreen

20
Pd(PPh3)4
K2CO3, R"X

R' O

Ts

NHTs

TBAC,

N
O

R
R'

R"

(5581%)
R = R' = H, Me; R = Me, R' = Et; R+R' = (CH2)n, n = 4, 5;
R"X = PhI, p-MeOC6H4I, p-NO2C6H4I,
OTf , I

t -Bu

Cl
N

n-BuLi
, Pd(OAc)2, PPh3 3 . (2-) - [24].
-
2,3,4,5- 45 . 5 . %
PdCl2(MeCN)2 (12 ) 45a 70% [25] ( 21).
21

Au(III)
R'
( )3

NH2

R
H 2N
R'

N
H

R'
R

R'

45a, b

a R = n-Hex; R' = H;
b R = n-Pent, R' = Me

i - 5 .% AuCl3 2H2O MeCN ~ 20C

46e
[17, 26] ( 22).
22

R
O
R'

R"

MeNH2

R'

OH
N
H
R"

PdCl2

R"

MeCN

46a, b
a R = n-Hex, R' = H, R" = Me (50%);
b R = Et, R'+R" = (CH2)4 (30%)

, 2

R'

85

R'

LiAlH4

NH2

R'

PdCl2
MeCN

OR"

OR"

H
N

R'

46ce
c R = n-Hex, R' = Et (84%);
d R = n-Hex, R' = t-Bu (84%);
e R = Ph, R' = Et (>90%)

,
,
46.
: H2PtCl3.6H2O, AgOCOCH3, CuCl, RhCl3.H2O, WiCl2, SnCl4
AlCl3 [26].
47 [17]
( 23).
23

H2N

O
OSiMe3

MeSiCN

(CH2)10

OH

LiAlH4

(CH2)10

(CH2)10
H
N

PdCl2
MeCN

(CH2)10
47 (82%)

[27, 28], 2--1,3-


- ,
5060 2-R-3--5- 48. , ,
,
48 ( 24).
24
R
NH4Cl

CuCl, O2
R'OH/H2O
5060C

R
R = Me

86

R
O
R

NH2

N
H
48 (49%)

InterBioScreen

[17, 26] -, - 2--3--1- 49a


( 25).
25

R'
R
R"
O

R'
i

O
HO

R"

49a (6075% (1);


8094% (2), (3))

R'

R"

R = Et, n-Hex; R', R'' = (CH2)4, H, Me;


i - (1) PdCl2 (0.05 .) . MeCN, , 3 ;
(2) PdCl2 (PhCN)2 (0.05 .) . , .., 5 ;
(3) PdCl2 (0.05 .) . MeCN, .., 5

2,3,5- 49b
2- 1,3- -
[29] ( 26).
26

O
O

OMe

49b (56% R = Me)

Pd(II) 2-
,
, - 50 [30] ( 27).
27
R

R"

R'
OLi

R
CO2

R"
R'

O
O
OLi

Pd(II)

Pd(II)

R'
R"

R
Cl

O
O

R'
R"

O
50 (5074%)

R = H, Me, Et, Bu, n-Hex, Ph, SiMe3; R', R" = H, Me;


Pd(II) = PdCl2(MeCN)2, 5 . %

, 2

87

2,3--4-1,4--2- 51 6--2- 52
N--N- ( 28). 100
(, ),
, CHCl3, , . , , . [31].
28

O
OH
R

HgO

, 100

R'
O

R'

R'

+
51 (2740%)

52 (1236%)

R = i-Bu, Bn, H; R' = Me, Ph

2- 53 54
N--2-
CuI . 2-() [32] ( 29).
29

R'
R

R'
N
R"

NH
R"

53
R = R' = H, R" = Bn (73%);
R = F, R' = H, R" = CHMePh (96%);
R = H, R' = n-Bu, R" = Bn (95%)

R' = SiMe3, n-Bu

NH
Ph

Bu- n

Ph

N
Bu- n
54 (84%)

i - CuI (0.5 .), CaCO3 (1 .), , 120C

, [33] [34] 80
2- 55
[3336]. 55 NaAuCl4.2H2O
88

InterBioScreen

510%.
. PdC AuC
55 [34, 35].
(
R'' = COOMe) PdCl2(MeCN)2
N--2--3- 56. ,
, 56 30% [34] ( 30).
30

R4
R2

R4

R1
NH

PdCl2(MeCN)2

Cl

Pd(II)

N
1
56 R

(R' = CO2Me)
ii

NH
R

PdCl(MeCN)2

R
N
R1

HCl

PdCl2(MeCN)2

N
R1
55

R = n-Bu, t-Bu, CH(Me)6H13, Ph; R1 = H, Ac, CO2Me;


R2 = H, Me, CH=CH2; R3 = H, Me, Cl; R4 = H, Me, Et;
i - PdCl2 (5 .%), MeCN NaAuCl42H2O, , ~20, Ar;
ii - PdCl2 (MeCN) (5 . %), (10 .), (10 .),
~20 Ar

5(6)- 2- PdCl2(MeCN)2 57 [35,


36] ( 31).
31

R
PdCl2

R'
NH
R"

MeCN

R'
N
R"

57 (3587%)

R = i-Pr, n-Bu, Ph, (CH2)2OSiMe3, (CH2)4CCSiMe3;


R' = 6-CO2Me, 6-OMe, 5-Me, 5-Cl, 5-OTf; R'' = H, Ac

, 2

89

2- 2-
CH2Cl2HCl Bu4NCl PdCl2 [37].
(-)
[2,3-a] 58 ,
[38] ( 32).
32

Ph

Br

HN

NH

O
Br

CF3

O
O

CF3

Ph
N

N
H

N
H
58

Pd(II) 3--1,2,4-5(2)- 59 -1,2,4-,



60 [39] ( 33).
33
R
O

N
N

NH

i ii

N
N

S
R'

S
R'

+
O

R'
S

O
59 (4370%)

60 (7387%)

R = H, Me, Ph; R' = H, Me;


i - PdCl2(PhCN)2 25 .%, MeCN , ;
ii - NaOH 1050 .%, MeOH,

90

InterBioScreen

4-()-2(1),
-5- 61 [40]
( 34).
34

Cl

Cl

Pd

R"'
R"'

R"
N

Cl

R"

HN

S
R

S
O

R
N

R"'

N
O

R
N

R'

R'

HCl

L R"
S

R"'

PdCl2L2

Pd

R'

R"
S
N

R
N
R'
61 (3593%)

R = H, Me, F, Br; R', R", R'" = H, Me;


i - PdCl2(PhCN)2 (110 .%), ( MeCN, MeOH),

2-()
5 . % Pd(PPh3)4
3--4- 62 4050% 63
2030%. 2-()
63 60%. 62 63

, -Csp2- , [41] ( 35).
, 2

91

35
Ar
R

R = Alk

L
I Pd Ar

N
62

OMe

Ar

R = Ar

MeO

R
N

63

i - ArI, Pd(PPh3)4, NaOMe, MeOH, , 24

OMe

, sp2-sp- , , ,
(I) [4244].
.
[4248].
64, (
65) Pd(OAc)2/TPPTS
(TPPTS ) ,
(I). ,
, .
one pot- sp2-sp-
[49, 50]
( 36).
36

L L
R

R'

+
X

R
X

R'

R'
X
64ae (5799%)

X = NH2, NHC(O)CF3, OH;


R' = n-Bu, CEt2NH2, CH(OH)C6H11, CMe2OH;
R = H, X = NH (a); R = H, X = NC(O)CF3 (b); R = H, X = O (c); R = CHO, X = O (d);
i - Pd(OAc)2/TPPTS (1 : 2) 2.5 .%, Et3N 2.5 ., MeCN/H2O (15 : 1), 2065C

92

InterBioScreen

,
, -
65 [51] ( 37).
37
O

OMe
OH

+
Cl

SiMe3

Pd(0)/Cu(I)

Cl

I
HN

OMe

HN

Ac

Ac

65

,
, -
66, 67 [52] ( 38).
38

I
O

O
66

67 (63%)

i - 3 .% Pd(PPh3)4, 2 . Et3N MeCN, 16

- 80C Pd(OAc)2(PPh3)2, CuI


Et3N 2-- 2-[b] 68
4287%. 2,3- [b] 69, (, Y = H, RX = 5- 69
33%) [53] ( 39). , 68
sp2-sp-, , 69 -Csp2 2-
,
-- L2Pd0 - B.
, 2

93

39
RX
L2Pd(0)

L2Pd(0)

HX

L2XPdR

OH
R
Y

LXPdR

L2XPdR

OH
A

PdL2R

HX

OH

L2Pd(0)

Y
R

O
69

68 (4287%)
Y = H, CN, Me; R = , , ; X = Br, I , OTf

69 , , .
n-Bu4NF,
t-BuOK, 68 .
-

2,3- [b] 70 ,
-- - , in situ.
KOAc Pd(PPh3)4
[53] ( 40).
40

SiMe3
Y

RX

i ii

Y
R
O

OAc
68

94

InterBioScreen

R'
Y

iii

RX

R'
O

OH
70

i - Pd(PPh3)4, Et3N, n-Bu4NF, , 60C;


ii - Pd(PPh3)4, t-BuOK, NMP, 80C;
iii - Pd(PPh3)4, KOAc, MeCN, 45C

, - - ,
[54], [55]
[56, 57]. 71ad
(II)
- 72, 74, 75 [58] ( 41).
41

R'
R

OH

O
O

i ii

Ph

R'
Ph

R
72a, b (100%)

71ac

74c (9% ,
41% )

73c (83%)

OH
Ph

OH

OH
O
71d

MeO

O
ii

O
O

Ph
75d (88%)

a R = R' = H; b R = H, R' = O

75e

O ; c R = Ph, R' = H;

i - HgO (0.0040.06 .), 60,


, , , d;
ii - , , HgO

71a 72a
HgO 75e.
4- , Pd(II), - 76
[59] ( 42).
, 2

95

42

R
R

Pd(II)

Pd(II)

R
O

Pd(II)

OH
O

76

, 77
[60] ( 43).
43
3

R
R
R
O

( )n

Pd(II)

Pd(II)

Cl
R

( )n

OLi

R3

Pd(II)

( )n
O

77 (3794%)
R = H, Ph, SiMe3; R1, R2, R3 = H, Me; n = 2, 3, 4;
i - PdCl2(MeCN)2 5 .%, 20 ., , ~20C, 5

3-
- -, 3--3--4- 78 ( 44).
44

O
OLi

Pd(II)

Cl

R
R = n-C6H13

78


,-
-2- 79, 80 - 81
40 85% [61] ( 45).
96

InterBioScreen

45

O
O

OLi

( )n

ii

R'

R'

n=0

79

R'

n=0

80

O
R'

i
R = H, n-Pr, n-Bu, Ph; R' = H, Me;
i - 5 .% Pd(OAc)2, 200 .% LiBr;
ii - 5 .% Pd(OAc)2, 10 .% LiBr

81

n=1

, , Nu
, ,-
. 79. 80
- ( 46).
46
R
Nu

O
R'

79

H
Pd(II)

+
H

Pd(II)
O

R
Nu
R'

Nu

O
R'

80

Pd(II)
R'
A

R
Nu
R"
O

Pd(II)
R'
B

, 2

Nu
97

82
3- 3,5- 4- [62] ( 47).
47
R
R'

R
R'

Pd

OH

R"

R"

82ac

a R = R' = R" = H; b R = H, R'+R" = OCH2O; c R = Me, R' = R" = H

83, , 2- -3-
-
[63] ( 48).
48

R'

OH

R'

OAc
R"

R"
O

83

R = H, Me; R' = R'' = Me; R = R' = H; R'' = Ph; R = H, R'+R'' = (CH2)n;


i - Pd(OAc)2, (2-), K2CO3,

3- ,
. -
3-
84 [64] ( 49), 3- 85,
, [42], .
49
R
I
O

OH

CuC

O
84 (5060%)

85

R = n-Pr, n-Bu

98

InterBioScreen

3-R- 84 (R = n-Pr, n-Bu, CH2OCH3, CMe2OH,


CH2OH, Ph, p-MeC6H4) 96% -
Pd(PPh3)4, Et3N
ZnCl2 [65]. 86 85
( 50).
50
R

R
O

84

85

O
O

OH

86

R = H ( 85), n-Pr, n-Bu, CH2OMe, Ph

-(1-) ZnCl2 Et3N


3-- 84. , ZnCl2 . ,
- , -(1-) ( 51).
51

R
I
O

Pd(PPh3)4

Et3N

O Et3NH

O Et3NH

ZnCl
R

ZnCl2

+
Et3NH

R
O

O
O

O
84

, 2

99

- -() . 100 :
3-(2-) 87 88 95 : 5 ( 52).

52

SiMe3
O
OH

NH
CF3

O
O

O
O
N
H
87

88

N
H

,
- , , 87.
Pd(PPh3)4-ZnCl2-Et3N
Pd(PPh3)2Cl2-CuI-Et3N -
3- [66].

1.
2.
3.
4.
100

., .., , .: , 1973, . 326.


.., .., .., ..,
,
. .., .., - . -, 1971, c. 97.
Viola A., Collins J.J., Filipp N., Tetrahedron 1981 37 (22) 3765.
Patterson J.M., Synthesis 1976 (5) 281.
InterBioScreen

5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.

.., .., .., , .: , 1993.


.., .., .., . .
. , .: , 1991, . 224.
Gilmour D.W., Roberts J.S., UK Patent 1 468 046.
Chiusoli G.P., J. Org. Chem. 1986 300 (12) 57.
Chiusoli G.P., Transition Met. Chem. 1983 8 (3) 189.
Burns B., Grigg R., Sridharan V., Tetrahedron Lett. 1988 29 (34) 4325.
Grigg R., Dorrity M.J., Malone J.F., Tetrahedron Lett. 1990 31 (9) 1343.
Lu X., Xie X., Jiang H., Abstr. pre-OMCOS Symposium "Organometallic and
Catalysis", University of Rennes, Rennes (France), 1999, p. 2.
Piquet M., Bruneau C., Dixneuf P.H., Chem. Commun. 1998 (20) 2249.
Semeril D., Piquet M., Bruneau C., Dixneuf P.H., Abstr. pre-OMCOS Symposium
"Organometallic and Catalysis", Rennes (France), 1999, p. 68.
Barrett A.G.M., Baugh S.P.D., Braddock D.C., et al., Chem. Commun. 1997 1375.
Trost B.M., Krisch M.J., Synlett 1988 1.
Utimoto K., Pure & Appl. Chem. 1983 55 (11) 1845.
Saito T., Morimoto M., Akiyama C., et al., J. Am. Chem. Soc. 1995 117 (43) 10757.
Riediker M., Schwartz J., J. Am. Chem. Soc. 1982 104 (21) 5842.
Luo F.T., Wang R.T., Schreuder I., Youji Huaxue 1993 13 (3) 297.
Wolf L.B., Tijen K.C.M.F., Rutjes F.P.J.T., et al., Tetrahedron Lett. 1998 39 5081.
Arcadi A., Synlett 1997 941.
Bouyssi D., Cavicchioli M., Balme G., Synlett 1997 944.
Luo F.T., Wang R.T., Tetrahedron Lett. 1992 33 (45) 6835.
Fukuda Y., Utimoto K., Nozaki M., Heterocycles 1987 25 297.
Utimoto K., Miwa H., Nozaki M., Tetrahedron Lett. 1981 22 (43) 4277.
.., .
.: - . . .. , , 2001, . 76, . 101.
.., .., .., .., .
, . .., .., .:
-, 2001, . 2, . 65.
Arcadi A., Cacchi S., Larock R.C., Marinelli F., Tetrahedron Lett. 1993 34 (17) 2813.
Iritani K., Yanagihara N., Utimoto K., J. Org. Chem. 1986 51 (26) 5499.
Yamamoto M., Tanaba S., Naruchi K., Yamada K., Synthesis 1982 (10) 850.
Fujiwara J., Fukutani Y., Sano H., et al., J. Am. Chem. Soc. 1983 105 (24) 7177.
Taylor E.G., Katz A.H., Salgado-Zamora H., Mc Killop A., Tetrahedron Lett. 1985
26 (48) 5963.
Iritani K., Matsubara S., Utimoto K., Tetrahedron Lett. 1988 29 (15) 1799.
Rudisill D.E., Stille J.K., J. Org. Chem. 1989 54 5856.
Arcadi A., Cacchi S., Marinelli F., Tetrahedron Lett. 1989 30 (19) 2581.
Cacchi S., Carnicelli V., Marinelli F., J. Org. Chem. 1994 475 (12) 289.
Saulnier M.G., Frennesson D.B., Deshpande M.S., Vyas D.M., Tetrahedron Lett.
1995 36 (43) 7841.
Mizutani M., Sanemitsu Y., Tamaru Y., Yoshida Z.-I., Tetrahedron Lett. 1985 26
(9) 1237.
Mizutani M., Sanemitsu Y., Tamaru Y., Yoshida Z.-I., Tetrahedron 1986 42
(1) 305.

, 2

101

41. Wu M.-J., Wei L.-M., Lin C.-F., Abstr. pre-OMCOS Symposium "Organometallic
and Catalysis", University of Rennes, Rennes (France), 1999, p. 76.
42. Castro C.E., Gaughan E.J., Owsley D.C., J. Org. Chem. 1966 31 4071.
43. Haglund O., Nillson M., Synlett 1981 (10) 671.
44. Sakamoto T., Kondo Y., Iwashita S., et al., Chem. Pharm. Bull. 1988 36 (4) 1305.
45. Larock R.C., Yum E.K., J. Am. Chem. Soc. 1991 113 (17) 6689.
46. Wensbo D., Eriksson A., Jeschke T., et al., Tetrahedron Lett. 1993 34 (17) 2823.
47. Arcadi A., Cacchi S., Marinelli F., Tetrahedron Lett. 1992 33 3815.
48. Heck R.F., Palladium Reagents in Organic Synthesis, London: Academic Press,
1985.
49. Amatore C., Blart E., Genet J.P., et al., J. Org. Chem. 1995 60 (21) 6829.
50. Genet J.P., Blart E., Savignac M., Synlett 1992 715.
51. Candiani I., De Berandinis S., Carbi W., et al., Synlett 1993 (4) 269.
52. Zhang Y., Negishi E.-I., J. Am. Chem. Soc. 1989 111 (9) 3455.
53. Arcadi A., Cacchi S., Del Rosario M., et al., J. Org. Chem. 1996 61 (26) 9280.
54. Iino Y., Tanaka A., Yamashita K., Agric. and Biol. Chem. (Jpn.) 1972 36 2505.
55. Kupchan S.M., Britto R.W., Ziegler M.F., et al., J. Am. Chem. Soc. 1973 95 1335.
56. Dickens F., Jones H.E.H., Brit. J. Cancer 1961 15 85.
57. Dickens F., Jones H.E.H., Waynforth H.B., Brit. J. Cancer 1966 20 134.
58. Yamamoto M., J. Chem. Soc. Chem. Commun. 1978 15 649.
59. Lambert C., Utimoto K., Nosaki H., Tetrahedron Lett. 1984 25 5323.
60. Yanagihara N., Lambert C., Iritani K., et al., J. Am. Chem. Soc. 1986 108
(10) 2753.
61. Wang Z., Lu X., J. Org. Chem. 1996 61 (7) 2254.
62. Cavicchioli M., Bouyssi D., Gore J., Balme G., Tetrahedron Lett. 1996 37 (9) 1429.
63. Bouyssi D., Gore J., Balme G., et al., Tetrahedron Lett. 1993 34 (19) 3129.
64. Batu G., Stevenson R., J. Org. Chem. 1980 45 (8) 1532.
65. Castro C.E., Gaughan E.J., Owsley D.C., J. Org. Chem. 1966 31 4071.
66. Liao H.-Y., Cheng C.-H., J. Org. Chem. 1995 60 3711.

102

InterBioScreen


.., .., .., ..

660049, , . , 89
, [1].

, "" .
[1,9-cd]-6(1H)- () 1 2, 2 5,
[2].
R'
N N
X
O

HN

R''

1 X = CH;
2X=N

,
1--9,10-

, ,
.
, ,
, , , ,
,
..
. , 1--9,10- [3],
,
[3],
[4]. ,
.
- .
, 2

103

1. 3,5--6H-6-[1,9-cd]
[5], 3,5--6H-6-[1,9-cd] 3 1020 5-3--6(6H)-[1,9-cd] 4 3,5--6(6H)-[1,9-cd] 5.

O N
O
R
O

3ae

H
N

O N

O N

O
R
O

N
4ae

+
N

O
5

R = H (a), o-Me (b), m-Me (c), p-Me (d), p-t-Bu (e)

, 6--3,5-(-)-6H-[1,9-cd] 3b 4b 5, 4050C
4b 5.
515C
4050C 5.
5 3 3b [6] - 67 6 -
.
104

InterBioScreen

O N
X

X
HN

R'
R''

O N

O N

+ R'
X N
H R"

O N

R'

R"

X 7

R'
N

O N

X = Cl, Br

+ R'
N
R''
H

R"

- , 6- [7],
5 3.
, , 3b
5 4b . 5 , -, .
H
N

O N
N

3b

H
N

5
O

8b

, 2

105

, ()
5 3b, 8b -
9ab .
O N

H
N

H
N

3b, 8b
+

N H

9
(a); N

R= O

(b)

, 5, ,
.
H
N

H
N

4b

3b

8b

3b 3b5 ,
5.
4b 5 . 4b 10b
[5].

O N
O

, PhBr
O

HN

4b

HN
O

HBr

O
10b

106

HN
Br

InterBioScreen

10b ""
, 11.

HN

O
O

HN

HN

HN

HN

Br(I)

10b

11

3,5--6--6H-[1,9-cd] 5 , . 12
[5].
X
O N

O N
N

NH

HX

O HN

O
5

12

O N
HN

H
N

HN
N

X = Cl, Br, I

,
1--9,10- [8],
, 5--6--6H-[1,9-cd] [9].
, 2

107

2. 7-[2,3-b]-8,13-
[5], 7-[2,3-b]-8,13- 13 , .

R
O

HN
O

OH

HN
O

H2N

HN

R
13

OH

14

R = H (a), o-Me (b), m-Me (c), p-Me (d), p-t-Bu (e)

13 , 1-3-. , , .

R
O
H 2N

HN
O

NH2

15

HN

HN

NH2

13

R
H 2N

OH

16

HN

OH

14, 16,

,
-NH-(CH2)n-NR'R'', 11, 17. ,
108

InterBioScreen

14, 16
[5].
. 14
16 18, 19.

R
O

HN

HN

O
O

HN

PhSO2Cl

( )n
OH

14, 16

HN

( )n
O
O
S
O

18

R
HN

HN
19

( )n
Cl

R = H, Alk; n = 2 (14), 3 (16)

18, 19 .

R
O HN
HN

18, 19
O HN

N
( )n

n = 2 (11), 3 (17)

, 2

109

1--9,10--2- 20 [10] 1-(2-)-9,10--2- 21, .

OH
O

NO2 O
OH H2N

HN

OH

OH
O

O
20

OH
O HN

HN

HN

O
N

O
O

O
21

1-(3-)-9,10--2- 22
.
23, -
1-(3-)-9,10- 24.
O

O
O HN

OH

O HN
20

OH

AcOH

NH2

OH

O
OH

23
Cl
Cl

O HN

OH

O
22

O
24

110

InterBioScreen

20 , ,
26.

NO2 O

O
20

SOCl2

R
HN

Cl

NO2 O

N
R

N3

NaN3

R
+
N N R
O

N
R

25

HN

HN

R
N

O
N

O
26

[11] 25
,
.

- [12]. , 2--3--1,4- 27
- 3- 28.

O
N

O
N

NaNO2

OH

Cl
O

27

28

29 30 1--2-
NaNO2
1- 31, 32.
, 2

111

NO2 O

O
O

O
31

NO2 O

O
N
H

NaNO2

29

OH

OH

NaNO2

O
N
H

30

32

, 29 31 ,
29 KF . -,
- -, 33
31.
O
F

29

O
O

NO2

NO2

31

O
33

1.
2.
3.
4.
5.

Krapcho A.P., Maresch M.J., Hacker M.P., et al., Curr. Med. Chem. 1995 2 803.
Krapcho A.P., Menta E., Oliva A., et al., J. Med. Chem. 1998 41 5429.
Krapcho A.P., Petry M.E., Landi J.J., et al., J. Heterocycl. Chem. 1993 30 1565.
Oliva A., Ellis M., Fiocchi L., et al., J. Heterocycl. Chem. 2000 37 47.
.., .., . : . . 2002 45
(6) 152.
6. .., .., .., 1992 28 (4) 842.
7. .., .., .. ., 1990 26 (1) 188.
8. .., .., .., . , . . 1965
(11) 121.
9. .., .., .., 1984 (7) 885.
10. .., .., .., 2001 37 (9) 1321.
11. .., .., .., .., 1986 22
(11) 2357.
12. .., .., .., . . . .
. " ", .: , 1999,
. -134.
112

InterBioScreen


.., ..
. ..
, 1, [1, 2].
[35].
1958 . , 4--3--1-- 4--5-1- ,
; [6]. 4
3 5.
, 3 5,
4,
( 1). 5- 3- 1 3 , 2 4 [7].
1
NH2

N
N
R
1

H2N

N R
2

N
N
R
3

N
4

N
N
R

.
3--1-
; 5- , .
5--3-, 5--3-(-)- 5--3-(-)-1-. N- (~15%). 5--3-(-)
.
, 2

113

, 1- , , 5--3-(-)-1- 5 60%, 6
( 2).
2
N

H2N
NH2

N N
Ph

N
5

N
N
Ph

5--3--1- 7,
5--3--1- 8 9,

10 11 [8, 9] ( 3).
3

H2N

N
N
Ph

N
N Ph AcOH

120C

120C

HO

NH

N
N
Ph

N
H

10

N
N Ph

MeO

NH
O

220C

N
N
Ph

N
H
11

,
( , . 3), [8], .
,
, 10
114

InterBioScreen

, 11 (2- 1500
, 4- [10]). [2, 3],
7-[3,4-b] 11, ,
9 ,
5-[3,4-b] 10. , ( 150 ) 5-[3,4-b]. , (. ),
.
, , , ,
, 60- . [1016],
.
, .
12 5--1,3- 13 14 ( 4). 1
(15%),
14 [17].
4

CF3
O

O
OEt

F3 C

+
H2N

12

CF3

N
N

N
O

13

14 (85%)

OH

N
HO

N
14a

N
H

N
F3C

N
H

15 (15%)

N
F3C

16

, , (85 : 15) 1
-d6 C6D6, , 1,3--7--5-()[3,4-b] 15. 1,
-d6 6D6 ,
- 15 16
. - ( )
1- 5- 150160 .
[3,4-b] 17, 18 6095% [18] ( 5).
, 2

115

5
R'

H2N

N
N
R

R'

N
N
R

O
R"

R"

R"

R"

17ad

17a R = Ph, R' = R" = Me;


17b R = Ph, R' = Me, R" = CF3;
17c R = R' = R" = Me;
17d R = R' = Me, R" = CF3

- 1- 5-.
[11], 5--3- 18
140 19, 5,7--2-[2,3-a] 20 ( 6). , 1 20 21.
19 .
6
Ph

H2 N

N
N
H

N N
20

18
O

Ph
N
N
19

Ph

N
H

NO

N N

Ph

21

[19] ( 7) 5- 22 - 23d
( ).
116

InterBioScreen

7
R
R'

O
N
N
H

H2N

R"

O
R"

R"
R'"

22ac

R'

N N

R'"
R"

24ah

23ad

22: R = Me, R' = H (a); R = Ph, R' = H (b); R = Et, R' = Me (c);
23: R" = Me, R"' = H (a); R" = R"' = Me (b); R" = CF3, R"' = H (c);
R" = Ph, R"' = H (d);
24: R = R" = Me, R' = R"' = H (a); R = Me, R' = R"' = H, R" = Ph (b);
R = Et, R' = R" = Me, R"' = H (c); R = R" = R"' = Me, R' = H (d);
R = Et, R' = R" = R"' = Me (e); R = Ph, R' = R"' = H, R" = Me (f);
R = Ph, R' = H, R" = R"' = Me (g); R = R" = Ph, R' = R"' = H (h)

23, 23b 23 ,
(2 , 140). 23d 160170.
, ,
1 22, 24c 24e 4- 5- 22. 24
1. ,
3- 22
3H-1--5,7-()[3,4-b] 25, 1- 5-
( 8).
=
23, 4 .
8

CF3
O
N
N
H

H2 N
22a

O
CF3

F3C
23c

N
F3 C

N
H

25

- 150 26, 27
28. 28 1.
, 2

117

, 26 27
1 .
5--3-,
2,5-[2,3-a]-7- 26 27
( 9). , ( 65100%)
[2,3-a]-7- 26, 1
. 5--3--, 5--4--3-- 5--3-;
, , , , , - [20].
9

R'

H
N
R

N N
O
R

H2N

O
N
N
H

R'

26

H
N
R

N N

OEt
R'

27

R'

R
N

N
H

N
H
28

5-
. , ,

-.
[4, 2124]. [25] 3--5- 1,7-[2,3-c]-5- 29.
[26]
(, ) [2,3-c]-5-,
.
-5- 1,
- - .
3- ( 10)
118

InterBioScreen

(I, II III). 29 30
1. 1,7-[2,3-c]-5-
31 . ,
[27]. 3--4-- 4--3--5- 32
33 .
10

N
O

O
29

HO

N
N
H

N
N
H

II

N
H

O
N N
30

O
III

N
N
H

O
31

Et

N
N
H

O
32

i -Pr

N
N
H

O
33

, 4 5, NH 1
. 3--, 3-- 3-(-)-5-, - , , , , ,
, -, -. :
145190 24 . 20 90%; - - . :
, 1
[28].
, 2

119

- 3-- 3-(-)-5-. [21],


2- .
-5-.
1 (170, 3 )
3--5- 3-(-)-5- -
2 (~4.15 ..), 34 35, 36 2
~3.5 ..

HO

N
O

N
H

34 R = Ph; 35 R = p-MeOC6H4; 36 R = Me


~0.50.8 .. 34
35, 1
10 12 .. ( NH -)
35 .. , 34
35 FeCl3.

N NH

N NH

OH

OH
O

O
34a

O
35a

34, , -
m/z = 31,
[2]+, . - 37
[31]+. , 180 37 37. ( 11), 300,
[31]+. 34 34 ,
280, 1
34 ,
34. 34
120

InterBioScreen

35 -
3 , , = .
11
N N

Ph
OH

180C

HO
O

O
37

N
N
Ph

37a

38 39, 38 6 40 ( 12).
12

N
N
H

39

N
N
H
38

HN

HO
O

HO
N N
H

40a

N N
40

, ,
. (
[13]) ,
16201800 1 , , =.
, 40,
, 2

121

1. 40,
-, ,
. , FeCl3.
38 (160, 3 ) ,
. 1-
-5- - ,
N- [2,3-c]-5-. ,
[29]
[30]. [31],
[25] 3--1--5-
100 , 140
[2,3-c]-5- (. 10). 3-1--5-, 1,3--5-, 3--1-(-)5-, - , ,
, -.
: (~10%) - 140180 24
[32] ( 13).
13
R'

N
N
R

OEt

R"
R'"

R"

R'

N
N
R

R'"

41ah

a R = Ph, R' = R" = Me, R"' = Et; b R = R" = Ph, R' = Me, R"' = H;
c R = Ph, R' = R" = Me, R"' = CH2CO2Et; d R = R' = R" = Me, R"' = H;
e R = R' = R" = Me, R"' = CH2CH2OH; f R = CH2CH2OCOCH2COMe,
R' = R" = Me, R"' = H; g R = CH2CH2OH, R' = R" = Me, R"' = H;
h R = Ph, R' = R" = Me, R"' = CH2CH2OH

, 1--5-
90100. , , 1,3--5-
100,
[33, 34] 41d,
70.
, 1--5- -, ,
. -
.
41g.
122

InterBioScreen

3--1-(-)-5-
, ,
, (. 14).
, 3
41f,
41g (.
[29]).
14
H
N

HO

NH2

N
N

OEt
O

OH

N
O

O
41g

N
O

OMe

OH

41f

-5- FeCl3,
5-, -5-,
- . ,
,
, ,
160180.
3--1--5- - 41h
(~15%), 1
Z-42 ( 15).
15

Ph
N

O
N

O
O

100C

O
O
HO

N
Ph

Z-42

, 2

123

HO
170C

O
41h

N
Ph

41h, 1 13,
(. [30]). 41h -
43. , Z- E-42 85 : 15 (. 16).
16

HO
HO

NaO

NaOH

N
Ph

HCl

O
NaO

H2O,

N
Ph

43

41h

O
O
O
HO

N
Ph

O
HO

N
Ph

Z-42 (85%)

E-42 (15%)

180C

41h
H
Z-42

E-42
O
O

124

N
Ph

InterBioScreen

Z- - , ,
, 180
41h, Z-. , Z- -
, 16,
. , - Z-42
[MCH2OH]+, . ,
( 300)
Z-42 41h,
ArCH2CH2OH [MCH2OH]+.

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.

, . , : -
, 1961, . 5, . 102.
Kost A.N., Grandberg I.I., in Advances in Heterocyclic Chemistry, Katritzky A.R.,
Ed., London: d. Press, 1966, v. 6, s. 347.
.., .., .., 1964 34 654.
.., .., .., 1965 35 1288.
.., .., .., .., 1963
33 2597.
Finar J., Hurlock R., J. Chem. Soc. 1958 3259.
.., 1961 31 1307.
.., .., .., 1964 34 2756.
.., .., .., 1965 (1) 116.
Checchi S., Ridi M., Papini P., Gazz.Chim. Ital. 1957 87 598.
Checchi S., Ridi M., Papini P., Gazz. Chim. Ital. 1955 85 1160.
Ridi M., Papini P., Checchi S., Gazz. Chim. Ital. 1961 91 973.
Checchi S., Ridi M., Papini P., Gazz. Chim. Ital. 1956 86 630.
Checchi S., Ridi M., Papini P., Gazz. Chim. Ital. 1955 85 1559.
Checchi S., Gazz. Chim. Ital. 1958 88 592.
Checchi S., Ridi M., Gazz. Chim. Ital. 1960 90 1093.
.., .., .., .., 1967 329.
.., .., .., , .
.., .., .., 2002 (11) 1555.
.., .., .., , .
Sing Shiv P., Kumar Dalip, et. al., Can. J. Chem. 2000 78 1109.
Orza J.M., Garcia M.V., Alkorta I., Elguero J., Spectrochim. Acta 2000 56 1469.
Jimenez J.A., Claramunt R.M., Escolastico C., Elguero J., Struct. Chem. 2000 11
(1) 77.
.., .., .. ., . 1965
(5) 210.
Wolf L., Ber. 1905 38 3036.
Khan M.A., Cosenza A.G., J. Heterocycl. Chem. 1982 19 1077.

, 2

125

27.
28.
29.
30.
31.
32.
33.
34.

126

Khan M.A., Pogotto M.C., Ellis G.P., Heterocycles 1977 6 983.


.., .., , .
Sheng-Chu Kuo, Huang Li Jian, Nakamura H., J. Med. Chem. 1984 27 539.
Sato M., Yasynobu K., Shimoji M., et al., Yakugaku Zasshi 1978 98 (3) 335.
Stolle R., Ber. 1905 38 3023.
.., .., , .
Elguero J., Jacquier R., Tarrago G., Bull. Soc. Chim. Fr. 1967 (10) 3780.
Alkorta I., Gonzales E., Jagerovic N., et al., J. Phys. Org. Chem. 2000 13 372.

InterBioScreen




.., ..
.
91011, , . , 2
.
,
, .

.
() 1 .

Alk O

1
R = H, Alk; X Y -

(SNVin). ,
SNVin
(. [14]),
, .
10
SNVin
.
1.
.

.
1,5-
. , - 2 , 2

127

()
3 30%- 2,4-3--5- 4,
[5] ( 1).
1
O

O
CH(OEt)3

EtO
EtO

NH4OH

EtO

Ac2O

OH

EtO

OEt
N

HO

OEt

, 5- , 5 6
, 2--1,2- 7 2- 8 [6] ( 2).
2
Ph

Ph

Ph
CN

NH2OH

O
N

Ph

Ph

Ph

CN

CN

EtO

NH2

ArNH2
6

NC

N
Ar

NH

9 10
SNVin 11, ()- (Z)-.
, (NaH ),
[2,3-b]-5- 12 [7], ( 3).
3
OMe

OEt AlkNH
2

OMe
H
N

O
O

10

Cl

Cl
S

S
Cl

128

Cl

11

O
Alk

NaH

O
OMe

Cl
S

N
Alk
12

InterBioScreen

13 10 SNVin 14
[2,3-b] 15 [8], ( 4).
4
OMe

OEt

OMe

O
HN

10

13

N
OMe

14

Alk

O
OMe

NaH

N
OMe

N
Alk
15

N
H

16
17 18 [9]
19, ( 5).
5
O

OAlk

AlkO

Xn

B
D

1. 17 2.

EtO

18

Xn

3. AcONH4

B
D

A
E

OAlk
OAlk

16
19 O
A, B, D, E = O, S, SO, SO2, RN, CO, CH, = ;
--D-E ;
= Hal, Alk, Alk, OH, CF3, Ph, Ar, Het; n = 06

20 () 21

22 [10] ( 6).
6
OEt
NC

R N

N
20

21

CN

NH3
R = C6H4CN, Ts

CN

N
N

22

, 2

NH2

129

-- --N
. , --N
, -
, .

. , 23 () 24 ( 7)
2(1)- 26, - . , ,
25, (2l2, ) [11].
,
[1216].
7
OEt
EtO

OEt
O

X
H2N

24

H2N

X O
OEt

CH2Cl2

OEt

Y = OEt, Het

O
25

23

O
24
EtOH

X
Y

OEt
N
H


EtOH

26
X = CN, CO2Et; Y = OEt, Het, AlkNH, ArNH

--N ,
[1721]. , ,
, SNVin
SNVin. , 8 27, 29, 31
, 28, 30, 32,
[17].
130

InterBioScreen

O
S

24

N
H

OEt

S
OEt

OEt

O
27

28

H
N

24

N
H

H
N

O
OEt

OEt
O

29

R'

R''
R"'

R'

24

OR

N
H

30

OEt

O
OR

R''
R"'
O

31

32

OEt

R = Me, Et; R' = H, Cl, Me, OMe; R" = H, Me; R"' = H, Cl

33 34 35 [20] ( 9).
9

MeO
NH

MeO

MeO

O
EtO

Ph

MeO
O

NH
OEt

OEt
33

34

Bz

35

, 2

131

10 24, 36, 41
37, C-C-N [2234],
SNVin, , ,
, 38.
4- 39, 40, 42, .
10

OEt
NC

+
O

BH
H2N

37

CN

CN

NH2 [2225]
CN

36

CN

H2N

38

39

BH

R = OEt, NHPh

O
24

37

CN

EtO

[26]

N
H

BH

40

O
37

F3 C
EtO

O
R

B
[2730]

CN

R
F 3C

S BH

42
41
R = -2-, Ph; B = N-

--N, 43 ( 11), [3553].


SNVin 45, 48, 50, 53
( Ph2CH, t-BuPh, Ph2O, -; , EtONa
, ) 46, 49, 51, 54.
44
3--4-() 46 [3547], 47 4--4 49 [48],
4--3- 51 [4951],
() 4-3- 54 [51]. 46 , , , 132

InterBioScreen

, , , 46a [42]
-, L-754394. 51 .
11
AlkO

NH2

AlkO

OAlk
O

43

N
H

OAlk
O

OAlk
45

44

OH

OAlk

MeO

N
H

OEt
O

46

46a

OMe O
O
O

N
R

O
47

N
R

NH2

43a

O
N

N
H
48

R = Ar, Het

O
O

N
H
49

NH2
21

N
H

NH2

CN

CN
CN

N
51

50

43

OEt
NC

H2N
N
N

H
43b

Ph

O
52

OEt

N
N N H
Ph

OH

OEt
CN

CN
N
N
Ph

53

, 2

N
54

133


. ,
SNVin 55.
5660 61 [52]. 60
( 12).
12
R
CO2Et

HN

N
H

57

R1

R = H, OH;
R2 = A

R = R2 = A

R
R

R
O
R

H
N

HN
O

R = A;
R4 = F

56

CO2Et
O

58

=A

NH
O

O
EtO2C

O
CO2Et

55
R1 = Me, CF3;
R3 = A

R = OH;
R4 = A

CO2Et
O
H
N

OH

O
O

CO2Et

HN

EtO2C
61

60

59

A = NHCH=C(CO2Et)2

, -N- --,
- (
-N-C) ( --). , 62
24, 63 23
1,6- 64.
SNVin 65, [5457] ( 13).
134

InterBioScreen

13

N
+

N
+

OEt

Br

+
Y

OEt

24, 63

N
K2CO3

64

CHCl3
EtOH

21, 24,
52, 63

62

OEt

N
21, 52

24, 63 X = CO2Et, NO2; Y = CO2Et;


21, 52 X = CO2Et, CN; Y = CN

CN

OEt
65

-N-- - ( 14) [3,2-e],


[2,3-c] 70. SNVin 66 67 68,
1- 70.
1,5-
69 [58].
14

( )n

( )n
OMe

NC

CN

N
CN

R
S

S
R' 66

R'

67

68

( )n
+

CN

S
R'

( )n

N
R

CN

R'

CN
CN

CN

69

70

R, R' = H, Me, Ph; R+R' = CH=CHCH=CH; n = 1, 2

, 2

135


.
71 , SNVin 72,
TsOH MeCN Et3N AcOH
MeOH 73 [59] ( 15).
15
OR

NH2

OR

N
H

24

N
H

OEt

OR

OEt

N
H

71

R = Me, Et

N
H
73

72

.
, 74
75, , ,
-, , 2--6--3,5- 76 [60] ( 16).
16

NC

CN
CN

HC(OEt)3

Py

NC

CN

NC

74

NC

HCl

CN
N

H2N

Cl

76

75

77 21 78,
HCl 79, [61] ( 17).
17
O
N

O
21

HCl

CN

CN

136

77

78

X = O, NMe

Cl

CN
79

InterBioScreen

,
.
( vinN) . 2- ,
3- 4- . - - 3 4
( ) .
2. 1
,
,
. . . , , 4--3- , ,

. -RTA , , ,
,
. , (+/+)--,
56lck , .
,
, , ,
. (, , ,
, , , , , , , ,
, , , ) ,
.
, ,
[63130]
, , [131184].
( 17)
80, 84 44, 52, 85, 88 SNVin
81, 86, 89, , , 82, 83, 87, 87a. :
1

, ,
. , ,
[62].

, 2

137

A, Ph2O, , , Ac2O + H2SO4,


, .
, ( , 70%)
, , Ph2O,
Ph2O. ,
, 1218 210250C.
84%, 96%. ,
Ph2O , [72].

- 44 4-()3- 82, 83 [63110, 118, 120], - 52, 85 88 4-3-R- 87 [103, 104, 111117] 87a [113, 118, 119] ( 18).
,
,
4-(). , ( .),
SNVin, .
18
O

OAlk
R'

NH

R"n
80

AlkO
AlkO
R
AlkO
44

OH
OAlk
R'

R"n

N
82

O
O

OAlk

R"n

O
81

OAlk
O

R"n
N
R'

83
R = H, Alk (C1C4), Ar, ArAlk; R' = Alk (C1C6), , CH=CH2, Bn, Ac, ArCH2, ;
R2 = H, Alk, Ar, Hal, OAlk, NHAlk; n = 14

138

InterBioScreen

OEt
AlkO
52, 85

EtO

Rn

OEt

Rn

NH2

O
X

Rn
N
H

N
H

O
O

86

87

84

O
88

Rn

NH

Rn

N
H

O
O

O
87a

89
X = CN, COAlk; R = H, Alk, Ar, Hal, OAlk, NHAlk; n = 14


POCl3, 4--3- 90,

[121] ( 19).
19
O

NH2
24

Rn
84

OEt

H
N
Rn

OEt
O

Cl
POCl3

OEt

Rn

81a

N
90

R = H, Alk, Ar, Hal; n = 14


. , 2--3,4- 84a 24
SNVin 81b,
91 LiClO4 NaH
PPh3 1,4- 81c.
83a,
. (R)- (S)- [122] ( 20).
, 2

139

20

24

OH

OH

O
91

NH2

84a

N
H

OEt

LiClO4, NaH;
PPh3

OEt

81b

O
F

C(CO2Et)2
N

OEt
N

O
83a

81c

81
-,
, -
.
,
, -, ,
, . , 80a 24 81d,
2 H2SO4
83b, [124, 125]
( 21).
21

R
F

NO2

Het

NH

24

NO2

Het

R'

R'

80a

81d
R = H, Me; R' = H, Me

F
C(COOEt)2 Het

O
OEt

N
R'
83b


[129]. 95,
,
140

InterBioScreen

92, () - 93 94 ( 22).
22

NH2
R

E
D

OH

O
X HC(OEt)3

OEt

165C

92

B
D

A
E

Ph2O

NH

200C

B
D

O
X

X
93

94

OEt

95

X = Ph, Ar, Het; R = H, Hal, OMe; A = B = D = E = CH = N

94
,
. , 9- 84b
SNVin 81e, 200C 96
[130] ( 23).
23
O
NH2

OEt

H
N

24

N
H

N
H

84b

81e

OEt
O

N
O

N
H
96

OEt OEt

97,
.
, , 98,
99. SNVin 100 , ,
: NaH , ,
, 2

141

N--2-, , , , , ;
23 Na2CO3 MeCN, , , ; 23
18--6 N; Et3N; t-BuOK t-BuOH
; KF NaF MeCN; NBu4F
; N2; .
, - ,
4--3- 101.
[131184] ( 24).
24
O
X
R'n

HC(OEt)3
+ Ac2O

HCO2Et

Hal
97

O
X
R'n
98

Hal

OEt

O
X

R'n
Hal

RNH2
99

N
H

X
R

R'n
N
R

101
100
R = Alk, , , , , Ar, Het, -1,
-2, CH=NOH, (CH2)3NMe2, CH(Me)CH2SPh, (CH2)2OPh, -3-;
R' = H, Alk, Ar, Het, Hal; X = CO2Alk, COCO2Et; n = 14

, ,

,
SNVin N- .

, .


.

,
. ,
142

InterBioScreen

.
, ,

.

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.

.., .., .., 2001 41.


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InterBioScreen

65. Venugopalan ., De Souza E.P., Sathe K.M., et al., Indian J. Chem., Sect. 1995
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InterBioScreen

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134. Sanchez J.P., Bridges A.J., Bucsh R., et al., J. Med. Chem. 1992 35 361.
135. Hagen S.E., Domagala J.M., Heifetz C.L., Johnson J., J. Med. Chem. 1991 34 1155.
136. Domagala J.M., Bridges A.J., Culbertson T.P., et al., J. Med. Chem. 1991 34 1142.
137. Culbertson T.P., Domagala J.M., Hagen S.E., Sanchez J.P.,
5 081 254; . 1993 1473.
138. Domagala J.M., Suto M.J., Turner W.R., 5 116 834; . 1993
1585.
139. Hagen S.E., Domagala J.M., J. Heterocycl. Chem. 1990 27 1609.
140. Renau T.E., Sanchez J.P., Domagala J.M., J. Heterocycl. Chem. 1996 33 1407.
141. Bouzard D., Di Cesare P., Essiz M., et al., J. Med. Chem. 1992 35 518.
142. Bouzard D., Di Cesare P., Essiz M., et al., J. Med. Chem. 1989 32 537.
143. Guillou C.C., Remuzon P., Bouzard D., et al., Tetrahedron 1998 54 83.
144. Bouzard D., Di Cesare P., Essiz M., et al., J. Med. Chem. 1990 33 1344.
145. Ledoussal B., Bouzard D., Coroneos E., J. Med. Chem. 1992 35 198.
146. Xiao W., Krishnan R., Lin Y.-I., et al., Pharm. Sci. 1989 78 585; . 1990
3504.
147. Moran D.B., Ziegler C.B., Dunne T.S., et al., J. Med. Chem. 1989 32 1313.
148. .., .., .., .., .-. .
1997 31 48.
149. .., .., .., .-. . 1997 31
(5) 23.
150. .., .., .. ., . , . . 2000 1234.
151. Augeri D.J., Fray A.H., Kleinman E.F., J. Heterocycl. Chem. 1990 27 1509.
152. Chu D.T.W., Nordeen C.W., Hardy D.J., et al., J. Med. Chem. 1991 34 168.
153. Brighty K.E., Lowe J.A., McGuirk P.R., . 8 905 643;
. 1990 5199.
154. Brighty K.E., Lowe J.A., McGuirk P.R., 5 037 834; . 1993
694.
155. Ekhato I.V., Huang C.C., J. Labell. Compds. Radiopharm. 1993 33 869; .
1994 23175.
156. Jrgens J., Schedletzky H., Heisig P., et al., Arch. Pharm. 1996 329 179.
157. Bartel S., Kleefeld G., Schulze T., et al., 4 303 657; . 1995
2155.
158. Laborde E., Kiely J.S., Culbertson T.P., Lesheski L.E., J. Med. Chem. 1993
36 1964.
159. Chen Y., Dai L., Yang B., Hong C., J. Chem. Eng. Chin. Univ. 1999 13 368;
. 2000 01115.
160. Okada T., Tsuji T., Tsushima T., et al., J. Heterocycl. Chem. 1991 28 1061.
161. Kuniyoshi M., Seigo S., Keiji H., Takayoshi I., 5 043 450; .
1993 151.
162. Iwata M., 5 073 556; . 1993 7141.
163. ., ., ., ., 37 261;
. 1993 7142.
, 2

147

164. Junichi M., Akira M., Masahiro F., et al., 5 164 392; . 1994
5114.
165. McGuirk P.R., Jefson M.R., Mann D.D., et al., J. Med. Chem. 1992 35 612.
166. Akira Y., Yoshiko N., Yoshihiro O., et al., 5 998 436; . 2000
23101.
167. Weber A., Bouzard D., Essiz M., et al., 4 965 273; . 1992
766.
168. Petersen U., Schenke T., Krebs A., et al., 3 906 365; . 1992
3153.
169. Petersen U., Krebs A., Schenke T., et al., 4 120 646; . 1994
696.
170. ., ., . ., 228 157; .
1991 1713.
171. ., P., ., 2 131 453; . 1991
1564.
172. Domagala J.M., Hagen S.E., Kiely J.S., 4 920 120; . 1991
14119.
173. ., ., . ., 64-83 067; . 1990
1340.
174. ., ., ., ., 63-198 664;
. 1990 9167.
175. Culbertson T.P., Domagala J.M., Hagen S.E., Sanchez J.P.,
4 929 613; . 1991 13195.
176. Hraki U., Hsashi M., Shinji A., Tatsuya O., 4 855 292; .
1991 21160.
177. ., ., ., ., 219 377;
. 1991 18175.
178. McQuirk P.R., . 91/04 972; . 1992 13144.
179. ., ., . ., 64-22 854; . 1990
5198.
180. Bridges A.J., Domagala J.M., 4 933 335; . 1991 23113.
181. ., ., . ., 2 124 873; . 1992
11132.
182. Miao H., Cecchetti V., Tabarrini O., Fravolini A., J. Heterocycl. Chem. 2000
37 297.
183. ., ., . ., 649 992; .
1990 1328.
184. Lipunova G.N., Nosova E.V., Charushin V.N., et al., Mendeleev Commun. 1998
(4) 131.

148

InterBioScreen


.., .., ..
. ..

480100, , . . , 106

, , .
[13].
()
.
1 N,N- 220250
2 [4, 5] ( 1).
1
O

O
R

R'

R'
2

[6] 2.
2

OH


[7, 8]. ,
1,4-(2-) 3 N,N-
, 2

149

[1,2-b:4,3-b] 4 [1,2-b:4,5-b] 5
1 : 1 ( 3).
3
O

+
O

O
3

2,7-(2-) 6
[2,1-b:7,8-b] 7 ( 4).
4

[9] - 8.
215 15 2 .
() -4- 9,
() 4- 10 ( 5).
5

R'
O

R''
R'''

R'
O

R'''
R

R''
R'''

O
9

R'

R''

Cl

Cl
8

10

R, R', R", R"' = H, Me, OMe, Cl

150

InterBioScreen

4-R-8-R'-7-(1,1-R''2--2-) 11
4-R-5-R'-6R''-7-(1-R'''--2-) 12
-2- [10] ( 6).
6
R

R
R''
O

R''

R'

R''
R''

R'

11

R'

R'

R''

R''
O

R'''

R'''
12

7-(-2-) 13 [2,3-h] [11] ( 7).


7

R
Ph

R
O

Ph

13

-5- 4-(4-R--2-) [12].


-
,
. [13] , , -
X-CH2CH2CCH, , -
.

[c]- ,
[b]- .
, ,
[2+4]-
, 2

151

(2)N(1)C(6)(5) . HC(3)N(4) ( )
HC(6)N(1) ( ) [b]- [c]- ( 8).
8

N
N
N

HCN

X = AcN, O, S, SO, SO2


[14]. , 5-(3--2-) 14 (R = H)
15, 5-(-2-) 14 (R = Me) 16 ( 9).
9

R = Ph

N
Ph

R=H

N
O

O
14

15

N
16

17
18 (, 195C), 2 - ,
[15],
( 10).
10

R
R

R
N
O

17

152

InterBioScreen

O
N

18

,
,
[16]. , 2- 3-() 19, 20 1,3- 21
( 11).
11

R
O

21

19

O
20


.
. ,
sp- 22 4--3- 23 [17] ( 12).
.
12
O

22

2+ +
Hg , H

OAc

OAc
23

1,6-(4-)-2,4- 24 6,6'--4,4'- 25 [18] ( 13).


, 2

153

13

24

25

1--4-()-2- 26
4-() 27,
[19, 20] ( 14).
14
O

O
S
26

S
Ph
27

, 4-(). 1,4-()2- 28 , 29 ( 15).


15
O
O
Ar

O
28

Ar
S

O
Ar S
O

O
S Ar
O

O
29

, N,N-(4--2-) 30, [21] ( 16).


154

InterBioScreen

16
O Ph

H
N

Cl

O Ph

30

OH

O
Cl

, 1,4-()-2-
[22].
-, - -() 31
32 [23] ( 17).
17

O
O

31

32

[24, 25].

33, -, - -() .

3436 ( 18).
18
R
O
O

33

R
O

R
R

+
O

34

35

36

R = Me2COH, cyclo-(CH2)5COH

, 2

155

()
,

. .
[26, 27] , 1--4-(3--1)-4 37 38 1,2- 39 ( 19).

N
H

HO

19

Ph

+
N

N
38

HO

37

39

N
H

R=
N


[28]. ()
40 -
(-) [1,2-b] 41, 42.
- - 43, ( 20).
20
R
O

HO
N

HO

O
N

156

O
OH

OH

41

R
O

Cl

40

42

R = H, Me, MeO

43
R = o-Cl, p-Cl

InterBioScreen

[29]. 60 44 ( = 2) -1- 44 ( = NMe) 7%


45 ( 21).
21
O

OH

OH

X
45

44
X = CH2, NMe

1--4--2- 46 47, 4 ( 22).


22

O
N

46

N
47

,
, - .
,

(
).

1.
2.

, . .., .: , 1973.
, . .., .: ,
1973.

, 2

157

3.

29.

.., .., .., , .: , 1993.


Thyagarajan B.S., Balasubramanian K.K., Rao R.B., Tetrahedron Lett. 1963
21 1393.
Thyagarajan B.S., Balasubramanian K.K., Rao R.B., Tetrahedron 1965 (21) 2289.
Zsindely J., Schmid H., Helv. Chim. Acta 1968 51 (7) 1510.
Majumdar K.S., Balasubramanian K.K., Rao R.B., J. Heterocycl. Chem. 1973 10
(2) 159.
Balasubramanian K.K., Venugopalan B., Tetrahedron Lett. 1973 29 2707.
Ariamala G., Balasubramanian K.H., Tetrahedron Lett. 1988 29 (28) 3487.
Rodighiero P., Manzini P., Pastorini C., et al., Tetrahedron 1987 24 (2) 485.
Prasunamba P.L., Srimannarayana G., Indian J. Chem., Sect. B 1989 28 (1) 71.
Majumdar K.S., Das D.P., Khan A.T., Synth. Commun. 1988 18 (1617) 2027.
De Bie D.A., Ostrowicz A., Geurtsen G., Van der Plas H.C., Tetrahedron 1988 44
(10) 2977.
Cshulte K.E., Reisch J., Mock A., Kander K.H., Arch. Pharm. 1963 296 235.
Biedrzycki M., De Bie D.A., Van der Plas H.C., Tetrahedron Lett. 1989 45 (19)
6211.
Biedrzycki M., De Bie D.A., Van der Plas H.C., Tetrahedron Lett. 1990 46 (2) 607.
Kapae C.., apaea .B., C A.M., 1984 53 (5) 853.
Balasubramanian K.K., Reddy K.V., Nagarajan R.A., Tetrahedron Lett. 1973
50 5003.
Viola A., Collins J.J., Fillipp N., Tetrahedron Lett. 1981 37 (22) 3765.
Thyagarajan B.S., Majumdar K.C., Bates D.K., J. Heterocycl. Chem. 1975 12
(1) 59.
Thyagarajan B.S., Majumdar K.C., J. Heterocycl. Chem. 1975 12 (1) 43.
Majumdar K.C., Thyagarajan B.S., J. Heterocycl. Chem. 1972 9 (3) 489.
.., .., . . .. , M.: AH CCCP,
1961, . 215.
.., ., .., 1983 19 (12) 2627.
., .., .., .., . ,
. . 1988 (1) 63.
., .., .., .., 1985
(4) 563.
.., .., ., 1989 25 (8) 1729.
.., .., .. ., . , . .
1992 (4) 50.
.., c. . . , , 1998.

158

InterBioScreen

4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.


..1, ..2, ..1, ..1
1


61002, , . , 53
2
. ..
61077, , . , 4
(2-1-, 2H--2-), - , .
2-1,3-, 2-1,4--2- (3- 4-),
2--2-, (5)-(6) .
:
5

5
3

6
7

2H-[3,2-b]-2-

2H-[3,2-c]-2-

2H-[2,3-c]-2-

2H-[2,3-b]-2-
5

N
3

7H-[2,3-d]-7-

6H-[3,2-c]-6-

4
3

N
N
8

2H-[2,3-d]-2-

, 2

159

, , ,
.


.
-
3 4
. 7--5--8- 2a 1934 [1] 2,6-4- 1a H2SO4
100 ( 1).

1
O
HO

OH
O

HO

N
1a

OH

OH

H2SO4

HO

2a

2,6- 1b 7--8-
2b, 8% [2].
2-- 2,6-
H2SO4 ZnCl2 .
[2] 100
.
[3],
, .
2,6- 1b , 2b (15%)
4,6--2,8--2,8-10-[1,2-b:5,4-b] 3a. 4,6-() 3b (50%)
[4] ( 2).
160

InterBioScreen

2
O

ZnCl2

OH

OEt

HO

HO

2b, c

1b

3a, b

R = Me (2b, 3a), CF3 (2c, 3b)

7--8- 2, 2,6- 1b 2,6--4- 1a ZnCl2, 4, 5 68 [5, 6]


( 3).
3
O

R'

O
OEt

R'
R" Cl

R"

HO

ZnCl2

OH

HO

R"

R'''

R'

N
O

R'"

4 (5391%)

Cl

KOH

R'
R"
O

N
O

R'
R"

R'''
O

6 (2361%)
KOH

R'

R'
R"
O

R"

[O]

R' = R'' = R''' = H, Me

, 2

161

1,2,3,4--1,8- 9 2-6,7,8,9--2-[2,3-b][1,8] 10 (1195%) [7] ( 4).


4
O

R"

O
OEt

R"

R'

ZnCl2

OH

R'

10

R' = H, Me, Ph; R" = Me, CF3

2--, 2-- 2--6-


8-. 2--6- 11 12
13 [4] ( 5).
5
O

OEt

H2N

OH

ZnCl2

H2N

11
R = Me, CF3

HO

N
H

13 (1520%)

12 (6180%)

12 63% 13 [4]. 7--8- 10, 12


[8].
14
[9],
2- [10] 2-[2,3-d]-2,4,7(1H,
3H)- 15 ( 6).
6

O
R'
X

R'''

N
N
R"
14

162

O
OEt

R'
X

R'''

N
R"

N
O

15
X = O, S; R' = R" = H, Ph; R''' = Ph, CO2Et;
X = O; R' = CONHMe; R" = R''' = Me

InterBioScreen

1,3- 14
1,3--1,2,3,4--5--4,7--2--7-[2,3-d] 15,
7,7- 16, [11, 12] ( 7).

7
O

R'

OEt

N
S

R'

H2SO4

R"MgBr

R'

R'
14

15 (7289%)

R'
N
S

R"
R"

R'
16 (6065%)
R' = H, 2-Me, 3-Me, 2-Cl, 3-Cl, 4-Cl, 2-OMe, 3-OMe, 4-OMe; R" = Me, Et


4--2(1)- 17
6- 18 19 - ,
: -, - 2--1- [13, 14, 15] ( 8).
, 2

163

OH
1

R
O
EtO2C

N
2
R

17

+
NH4OAc

CO2Et
+
NH4OAc

NH2

EtO2C

CO2Et

H2N

O
R2

HN
O

3
4

O
1

18

19

R1, R2 = H, Me; R3 = H, Me, Ph, CH2CO2Et; R4 = H, Bn

2- 20 2- 17
19, 21 6-, [16] ( 9).
9
R

OH

O
R

N
1
R

O
OEt

R3
4

NH4OH

19

17
R1 = H, Me, Ph; R2 = H, NMe2, NEt2;
R3 = Me, Et, Pr; R4 = H; R3+R4 = (CH2)4

164

InterBioScreen

R3
R2
1

OH

O
4

R1

OEt

NH4OAc

O
20

21
R1 = R3 = H; R2 = Me; R1+R2 = (CH2)3;
R2+R3 = (CH2)4; R4 = Me, CH2OMe

4--2(1) 17 -
- -
7085% [3,2-c]-2,5(6)-
19, 22
22 23, [17] ( 10).

10
O

R'''

OH

R"

R'
N
R"

NH4OAc

OH

R'''

POCl3

N
O

R'

19

17

Cl

R'''

Cl
N

R'
22

Cl

R'''

HN

+
R'

23

R' = H, 6-Cl, 8-Me; R" = H, Me; R''' = H, Me

6- 2426 6-4--2(1) 20 [17] ( 11).


, 2

165

11
O

OH

Na O

HN

N
H

NH4OAc

24 (68%)

20

O NH4OAc
O

OH

POCl3

HN
O

Cl

Cl
N
O

26 (66%)

25 (60%)

2--4--4- 27 - 4--2,5-2,5-[2,3-b] 28,


7,8,9,10- 29 (82%) [18]. 28
27 , 1--3,6--3,6-[3,2-] 30,
[2,3-b]- 31 ( 12).
12
O

OEt

H2N

H2/Pd

N
O

N
O

29

28 (65%)

O
N
OH

27

O
O

28 (5%)

+
O

+
O
30 (60%)

166

N
O

O
31 (2%)

InterBioScreen

- - , [19], [20], [21] N,N- [22].


4--2(1)- 20, N- 4--2(1)- 17 5,6,7,8- 32,
14, 5--6--3(2) 33 (Z)-2--3-- [23], (Z)-2-[(2,2--)]- [24], 2--3-- [25, 26] (2-)-3- [27]
3-N- 2-[3,2-c]-2,5- 34, 2-[3,2-c]-2,5- 35, 36, 7-[2,3-d]-7- 37, 2-[2,3-d]-2,5- 38 ( 13).
12 .
13
R'
NH

O
R"

N
O

HO

N
17 R"

35
R' = COMe;
R" = H, Me (7185%) [23, 26];
R' = CH=C(CO2Et)2;
R" = Me (65%) [24]
OH

NH

HN

O
Ph

H
N

N
O

O
HN
N

36

R' = COMe (67%) [23, 26]

HN
N

H
N
O

Ph

N
N
R"

14
O

O
OH
Ph
33

O
R"
X

R'

R'

34
R' = COMe (66%) [23];
R' = CH=C(CO2Et)2 (25%) [24];
R' = CO2CH2Ph (87%) [27]

R'

H
N

HN

20

OAlk
N
32 Ph

OH

R"
X

R'

38
R' = COMe (34%) [23];
R' = CH=C(CO2Et)2 (52%) [24];
R' = COPh (28%) [26]

H
N

N
N
R"

R'

37
R' = COMe; R" = H, Me;
X = O, S (6197%) [23];
R' = COPh; R" = H, Me;
X = O (8390%) [25];
R' = CO2CH2Ph; R" = H, Me;
X = O (7991%) [27]

, 2

167

4,6--2- 39 ,
[28]. ,
2--3- 40 (57%),
2-[2,3-d] 41 (71%) ( 14).
14
N

OH
N

+
N

OH

OH

OMe AcOH N
NH

Ph

OMe
Ph

HN
OH

40

39

Ph

OH

O
NH

N
N

41

N,N- 3 (42, X = N) 4--2(2)- (42, X = CH) 43


53% (X = N) 94% (X = ) [22] ( 15).
15
N

OH

CO2Et
CO2Et

X
N
H

42

OH

OEt
N

43

X = N, CH

4--7-N,N--2(1)- 17
2- 8-(N,N-)-3--2-[3,2-c]-2,5(6)- 44,
(max 515 ) [16] ( 16).
168

InterBioScreen

16
O

OH

OEt

HO
Ph

N
H

HN

AcONH4,

N
17

44 (63%)

45 - 4--5--5-[2,3-][3,2,1-jk]
46 (max 432 ) [16],
( 17).

17
O
O
H2N

N
OEt

O
45

46 (79%)

2-[2,3-d]-2,4,7-(1,3)- 37 (1485%) 14, N- 1- (, N,N-) [29,


30, 31]. 1,3-

.
4--2--5(4) 47,
14, 37. 5- 48,
. ,
[32] ( 18).
, 2

169

18
N

OEt

N
O
Ar
S

N
N
Ar

N
H

Py

EtO

OH

OEt

47

Ar

OEt

OEt

N
N
Ar

48

14

O
Ar

N
N
Ar

H
N
O

37
Ar = Ph, 2-MeC6H4, 2-MeOC6H4, 4-BrC6H4, 4-ClC6H4

,
1,3- 4--2--5(4)-
2-[2,3-d]-2,4,7-(1,3)- [33]. ( ),
(
). 4--2(1)- 17 . -
35 ( 19).
19
OH

N
O

N
H
17

OEt
O

H
N

HN
O

35 (69%)

2- 3-
14, 17, 20, 32 49 3-R- 5054 [34, 35]
( 20).
170

InterBioScreen

20

R'
O

O
N
O

17

O
N
H 20

Ph

49

Ph

51 (74%)
R' = Me [35]

N
N

N
O

R'
O

Ph

R'
O

N
14

32
OH

N
Ph

R'
O

OH

OAlk
O

54 (6272%)
R' = Ph, Bn

R'

O
N

R'
O

O
HN

50 (63%)
R' = Bn

OH

OH

53 (38%)
R' = Bn

52 (17%)
R' = COPh, Bn

3- 50, 52, 54 (1 : 1) Pd 3- (7398%) [34]. 2--3- 14


. [34] ,
3-2--3-(2,4,6--5-) 55 ,
6--2,4--7-[2,3-d]-7- 56 ( 21).
21
O

OH
N
HO

+
N
14

OH

OMe
AcOH

O
N

OH

Ph

..

N
HO

Ph

CO Me
OH 2

N
55

, 2

171

OH

AcONa

HO

56

Ph

4--2(2)- 20 14 1--4--5--2- 3- 57, 58 [36] ( 22).


22
O

O
R

NH
HO

N
Ph

HN

14
R = H, Me

Ph

MeO
O

Ph
O

OMe
R

HN
O

R
O

20

57

HN

OMe

N
O

O
N
R 58

4-
,
4--2--2- [37], .
, 59 N- [3740] ( 23).
23
OH

CH2(CO2Et)2

CH2(CO2Et)2

N
NH

17

OH

59

,
in situ 60,
4--6,7-[3,2-c]-2,5(6) 61 (43%) [41] ( 24).
172

InterBioScreen

24

OH

O
OH

Ph

N
Ph

AcOH, Ac2O

O
OH OH

AcOH, Ac2O
80C, 3

OH

N
Ph

Ph

Ph

OH

Ph

60

61 (4060%)

17, 27,
6264 -(2,4,6-) 4- 6571 (6590%) [18, 4245] ( 25).
25
O
Ar

N
N

OH

O
R"

O
CO2Me

OH

O
O

Ar

67

OH
64

27

R'

27

OH

OR

17

R"

R"

O
62

OH

OH

R'
O

OH

OH

62
OH
R"

R"

CN

71 R' = Ph, Bn;


R" = H, CO2Me, CO2H
O

R = 2,4,5-ClC6H2

68

OH

OR

O
O

OH

R'

R"

65

N
N

OH

CN

CO2Me
63

OH

O
Ph

69

R'

66 R' = Ph, Bn;


R" = Ph, Et

OH

70 R' = Ph, Bn;


R" = Ph, Bn

R"

, 2

173

4--5,6--2-[3,2-c]-2,5- 72 4--6--2(1)- 20
[46] ( 26).
26

OH

R'

R"

N
H

OH

R"

HN

O
R'

72 (2064%)

20
R' = H, COMe; R" = H, Me

3 : . [3]
5- 74
- 3--2- 73
( 27). 3--6--2- 6--5--3-
(2426%) [47].
27

O
N

O
Ar

OEt

OH

73

74 (1286%)

N
H

Ar =

Ar

,
NO2

3--4--2(2)- 75
, 6- 76 [48] ( 28).
174

InterBioScreen

28
OH

R"

O
N
R'

O
R'''

EtO

R'

R'''

N
O

O
R"

75

76

R' = Me, Ph; R" = H, Br;


R''' = Ph, 4-MeOC6H4, CO2Et, CONHPh, COMe

3--4--N--2(1)- 6- [49].
77.
, [3]
( 29).

29
HO

HN
Cl

O
H

OH

OH

O
Ar

.
N
H

77

Ar =
N

Ar

OEt

78 (2646%)

,
NO2

3- 5--8--7- 80 77
. ( 8.313.4; 20 90),
(7095%), .
79 ,
7- 80, 3- 81 [50] ( 30).
, 2

175

30

HO

Cl

CN

CN

H
HN +

HO

OH

R
OH

OH

77

+
H

80

79

HO

O
OH

R = CN

81
R = CN, Ph, SO2Ph, 4-NO2C6H4, 2-, 2-, 2-

(R = Ph, 4-NO26H4, 2-, 2-) . 3-(2-)-7- 82 ( 31).


31
HO

HN

O
+

NH2
H

N
SH

OH

Cl

AcOH

+
N

77

OH

N
S

82



. [51] 77 176

InterBioScreen

,
, 3--7- 83.
84, .
85
N--2-(4-) 86. 83 1N NaOH
, , 3-7- 87 ( 32).
32
O

HO

HO
OMe

OH

Ac
NH

NH2 Ac2O

H NH2
N

Ac
O

HN
Cl

Py

HN +
Cl

83 (63%)

77

84
NH4OH

NaOH

HO

HO

Ac
NH

OH
N

HN
Cl

85

87

NH4OH

HO

Ac
HN

OH
O

OH
86

1--3-4- 88. 3--6--3-[2,3-c]-3- 89 (6371%) 4-


90, [52] ( 33).
, 2

177

33
N

R"

R'

N
R"

Cl
R'

Ar

Ar
88

89

R"

R'

N
KCN

Br2

Ar

90
R' = Cl, NO2, OMe, Me, F, NH2;
R" = H, Me, OMe; X = O, NH, S

2--2- ,
1,3- .
(t-BuOK
). , 4--2- 17 1.5 3--2,4(2,4)- 91, 92 (3493%).
, [20, 5356]
( 34).
34
NH2

R'
N
R"

178

R'
N

O
CH(OEt)3

O
H
N

R"

OH

17

91

Ph

InterBioScreen

R'
N

R'''
NC

R"
O

R'''
O

92

R' = H, Me, Ph;


R" = 7-OH, 7-OMe, 7-NMe2;
R''' = CN, CO2Et, SO2Ph


93 [57]
[58] - , 1,3--6--1,2,3,4-4--7-[2,3-d]-7- 94 (6272%) ( 35).
35
O HN

O
R'
X

R"NH2

N
N
R'

CH(OEt)3

R'

OEt

R'

CN

N
R'

R" O

t-BuOK

OEt
N
R'

93

14

94

R' = Ph, 2-OMeC6H4, 2-MeC6H4, 4-ClC6H4, 4-MeC6H4;


R" = CSNH2, Ph; X = O, S

N,N--N-(6--4--3,6--5-) 95 , 4-6-[2,3-d]-7- 96 (5355%) [59] ( 36).


36
O

Cl

N
R

+
N
H

OH

95

OH

OEt
O

Na
OEt

EtOH
Me2NH
NaCl

N
R

OEt
N

96

R = H, Me, Ph

, 2

179

97
, 98, [3,2-c]3,6- 99 (5068%) [60, 61] ( 37).
37
N

OMe
CH(OMe)3

N
R'

Ac2O

R"

R"

97

N
R'

N
R'

99

98

R' = H, Me;
R" = CO2Me, CO2Et, CN, SO2Ph, 2-, 2-



- 3-(4--3-) ,
( , )
5- [3] 6- (45%) [62]. 2- 2--3- 8- (5071%)
[62, 63].
2--3-,
5--3- 100,
. [64] 100 , 101 5- 102 ( 38).
38
SO3Na

O
N

OH
O
100

NaHSO3

H2SO4

O
101

102

7--3- [65].
180

InterBioScreen

-8- 105 [66] 6-()2,4-[2,3-b]-5- 103,


- 104.
. 98%.
106 (94%). ( 39).
39
O
O

H
O

OH

AcCl

OH OH

103

104 (89%)

Ph

Ph

CF3SO3Me

O N
CF3SO3

106

105 (75%)


. 3--2-
5- (26%), 3--5- (12%) [3]. (3--2-) 107, 3--2-
73 , 108,
5- 109 [3] ( 40).
40
O
N

73

H
OH

O
OH OH

HO2C

CO2H

107

OH

, 2

181

OH
N

O
O

108

109

2-- 2--3- 110 c


3- 8- 111 [62, 63] ( 41).
41
O

O
R"

H
N
110

R"

OH
Ac2O/Et3N

O
R'

111
R' = H, Me;
R" = H, 4-F, 4-Br, 2-Cl, 4-OMe, 3,4,5-OMe

3--2(2)- 112 . 3--2-[2,3-b]2- 113 7080% [67]. 112


3--2[2,3-b]-2- 114 3040% [67] ( 42).
42
Ph

PhCH2CO2Na

Ac2O

R
N
H
112

113
R = H, 7-Me, 8-OMe, 9-OMe

O
O

N
H

OH

Et3N

H
N

R
N

114
R = 9-Me, 9-Cl

182

InterBioScreen

2--3--4- 115 5--2-[3,2-]-2- 116 [68] ( 43).


43

O
H

N
R'

(R"CH2CO)2O
Et3N

OH

R"

N
R'

115

116
R' = H, Me; R" = H, Ph


. [3] 3--2- 117 8- 118 ( 44).
44
O

OH
Ar

R
N
117

OH

Ac2O, Et3N

Ar
R
N

118

Ar = Ph, 4-F64, 4-Br64, 3-MeO64, 3,4,5-O62, 4-;


R = 7-OH, 7-Me, 5,7-Me2

3-(4-)-7- 3--2,5,7-6- [3].



[69] 2,4--3- 119 4-2- 120 , 121, 123125
, , 122
126 ( 45).
, 2

183

45
O
OMe O

HCl/
H H2O

OMe

OH

O
H

119

PPh3

OEt

OH

OEt

OMe

OMe

121

120
O
Ph3P

OEt

O
OMe

OEt

OH

OMe

KOH

OMe

OH
N

OMe

124

123

122

HCl/EtOH
15

O
OMe

OMe
OEt , h
N

N
H
125

O
126

[69]
5- 128 2--3- 73 [70].
(, , 60)
(75% 82%) - 127 ( 46). [62] , 128 (6772%).
184

InterBioScreen

46

OEt

O
O

OH

Ph3P

R"
O

R"

OEt
R"

OH Py . HCl

R'

220C

R'
73

N
R'
128

127
R' = H, Me; R" = Me, Ph

3--2-() 129 20 4-()-5- 130, 131,


4-()-2-[3,2-b]-2- 132 [71] ( 47).
47
O
O

O
+
Ph3P

S
OEt

Ac2O

OH

130 (77%)

129

I2 /MeOH

131 (63%)

N
O

132 (46%)


. ,
3- 133
1,3- 5-(2--3-) , 2

185

-4- 134, 135 [72] ( 48).


48
R'
O

N
N
R"

OEt
O

OEt R"NHNH2
N

R"

R'

NH

R'

134

133

N N

135

R' = Me, Ph; R" = H, Ph

4--2--4-[2,3-b]3- 133
134 136, 260 2--3--2-[3',4':4,5][2,3-b]-4- 135 (12%) 1--3--1-[5',4':4,5][2,3-b]-4- 137 (5%) [72] ( 49).
49

Ph

Ph
O

N
N

OEt
N

N
N

OEt
O

NH

Ph

NH

134

133

OEt

136

N N

N N

Ph

Ph

+
N

O
135

137

[73] [4,3-c] 3--3-(2,3--1--1-2- 138,


186

InterBioScreen

(5274%) 2-[(4--6-)-3-] 139. 6-[2][4,3-c]-6- 140,


141. 6-[4,3-c] 142,
.
143, 144 , [74, 75]
( 50).
50

O
EtO
O R"
R'

HO
N
N

O
EtONa

N N

R'
OH

R"
138

139

R'

NH4OAc

R"

Ac2O

R'

POCl3 N

R"

140

141

N
H

R"

142
AlkONa

R'
N

R"

N
143

NAlk2

Cl

NHAlk2

R'

R'

R"

OAlk

144
R' = H, Cl; R" = Me, Ph


3- 145 4--7- 149.
146,
3-() 147,
148 149
[76, 77] ( 51). 4--5-.
, 2

187

51
OCO2Et

HO

OCO2Et

OH ClCO2Et
Et3N

EtO

Mg

O
N

HCl

O
147

OH O

K2CO3
HCl

OH
OEt

N
148

120oC

EtO

146

145

CO2Et

CO2Et EtO2C

EtO2C

N
149

5--3--6-(2--1-)-2--2- 150a (R = Me) .


NH2 3--5--2-[3,2-c]-2- 151 (77%).
( 86%) [78].
151
2--3-(2--4--1,4--3) 152
(28%). ,
(78%) [78] ( 52).
52

Ph

NH

R
O

H
N

NH

R = Me

Ph

Ph
O

HN

151

OH

152

NH3 /EtOH
R = OEt

Ph

NH

EtO
O

188

NH3 /EtOH

NH4OAc/
AcOH
N

150a, b

H2N

153

Ph

NH

NH

HN
O
154

Ph

N
H

155

InterBioScreen

3--6-(2--1-)-5-2--2- 150b ,
153, 154,
3--2-[2,3-b]-2,5- 155 (62%) [78]. [78] ,
154 .
6--2--4--2H--3,5- 156 6,8-
157 [79] ( 53).
53

Ar

Ar

HN

HCO2H

H2N

157

156

5- [80] ( 54). 2-()-3- 158 159 (7090%).


-
13 160 (7290%).
54

A
ClCO2Et

Et3N

HO

HO

158

+
H

S
Cl

160

159
=

,
Cl

4,6--5- 161 4,6- 42 162 , 163


, [2,3-d] , 2

189

164. 1 : 1
15 21% 3-(N-) 165, 3- 166 (75%) [81] ( 55).
55

OH

HN

OH

161

NH

OH

162

42

HN
O
OH

OH
N
H

163

NH2

164

HN

O
N
H

HN

NH
N

N
OH

O
165

O
H

NH2

HN

OH
N

166

1.
2.
3.
4.
5.

Robinson R., Watt J.S., J. Chem. Soc. 1934 (10) 1536.


Galka G., Rocz. Chem. 1973 47 (9) 1747.
Moffett R.B., J. Org. Chem. 1970 35 (11) 3596.
Atkins R.L., Bliss D.E., J. Org. Chem. 1978 43 (10) 1975.
Chilin A., Rodighiero P., Pastorini G., Guiotto A., Gazz. Chim. Ital. 1988 118
(7) 513.
6. Guiotto A., Chilin A., Manzini P., et al., Farmaco 1995 50 (6) 479.
7. Henry R.A., Hammond P.R., J. Heterocycl. Chem. 1977 14 1109.
8. Shinkai M., Namiki T., Nakada H., et al., US Patent 5 104 740.
9. Schulte K.E., Mang R., Arch. Pharm. 1963 296 (6) 501.
10. Ridi M., Gazz. Chim. Ital. 1952 82 (1) 23.
11. Ahluwalia V.K., Batla R., Khurana A., Kumar R., Indian J. Chem., Sect. B 1990 29
(12) 1141.
190

InterBioScreen

12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.

Ahluwalia V.K., Kumar R., Khurana A., Bhatla R., Tetrahedron 1990 46 (11) 3953.
Kappe T., Baxevanidis G., Ziegler E., Monatsh. Chem. 1971 102 (5) 1392.
Kappe T., Mayer C., Synthesis 1981 (7) 524.
Habib N.S., Kappe T., Monatsh. Chem. 1984 115 (5) 1459.
Wolfbeis O.S., Monatsh. Chem. 1982 113 (3) 365.
Toche R.B., Jachak M.N., Sabnis R.W., Kappe T., J. Heterocycl. Chem. 1999 36
(2) 467.
Kappe T., Linnau Y., Liebigs Ann. Chem. 1972 761 (1) 25.
Schmidt H.-W., Schipfer R., Junek H., Liebigs Ann. Chem. 1983 (4) 695.
Ahluwalia V.K., Dudeja S., Sahay R., Kumar R., Indian J. Chem., Sect. B 1996 35
(12) 1319.
Schmidt H.-W., Junek H., Monatsh. Chem. 1978 109 (4) 1075.
Kusar M., Svete J., Stanovnik B., J. Heterocycl. Chem. 1996 33 (4) 1041.
Kralj L., Hvala A., Svete J., et al., J. Heterocycl. Chem. 1997 34 (1) 247.
Toplak R., Selic L., Sorsak G., Stanovnik B., Heterocycles 1997 45 (3) 555.
Stanovnik B., Svete J., Tisler M., J. Heterocycl. Chem. 1989 26 (5) 1273.
Kmetic M., Stanovnik B., Tisler M., Kappe T., Heterocycles 1993 35 (2) 1331.
Toplak R., Svete J., Stanovnik B., Grdadolnik S.G., J. Heterocycl. Chem. 1999
36 (1) 225.
Ornik B., Cadez Z., Stanovnik B., Tisler M., J. Heterocycl. Chem. 1990 27
(3) 1021.
Kepe V., Kocevar M., Polanc S., et al., Tetrahedron 1990 46 (6) 2081.
Cernigoj-Marzi A., Polanc S., Kocevar M., J. Heterocycl. Chem. 1997 34 (6) 1753.
Ahluwalia V.K., Sharma M.K., Sharma R., Indian J. Chem., Sect. B 1991 30
(10) 978.
Ahluwalia V.K., Sharma R., Sharma M.K., Indian J. Chem., Sect. B 1992 31
(10) 688.
Kepe V., Kocevar M., Petric A., et al., Heterocycles 1992 33 (2) 843.
Smodis J., Stanovnik B., Tetrahedron 1998 54 (33) 9799.
Escudero S., Perez D., Guitain E., Castedo L., J. Org. Chem. 1997 62 (10) 3028.
Skof M., Svete J., Stanovnik B., Heterocycles 1999 51 (5) 1051.
Kappe T., Aigner R., Hohengassner P., Stadlbauer W., J. Prakt. Chem., Chem. Ztg.
1994 336 (7) 596.
Faber K., Kappe T., J. Heterocycl. Chem. 1984 21 (6) 1881.
Kappe C.O., Kappe T., J. Heterocycl. Chem. 1989 26 (6) 1555.
Roschger P., Stadlbauer W., Liebigs Ann. Chem. 1990 (8) 821.
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Kappe T., Chirazi M.A.A., Ziegler E., Monatsh. Chem. 1972 103 (2) 426.
Nohammer G., Kappe T., Monatsh. Chem. 1976 107 (4) 859.
Dannhardt G., Meindl W., Gussmann S., et al., Eur. J. Med. Chem. 1987 22
(6) 505.
Schober B.D., Megyeri G., Kappe T., J. Heterocycl. Chem. 1989 26 (1) 169.
Ziegler E., Junek H., Herzog U., Monatsh. Chem. 1971 102 (5) 1626.
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(1) 81.
Gupta M.C.L.N., Rao V.S., Darbarwar M., Synth. Commun. 1990 20 (14) 2103.

, 2

191

49. Hafez E.A.A., Elnagdi M.H., Elagamey A.G.A., El-Taweel F.M.A.A., Heterocycles
1987 26 (4) 903.
50. Brufola G., Fringuelli F., Piermatti O., Pizzo F., Heterocycles 1997 45 (9) 1715.
51. Korytnyk W., Ahrens H., J. Heterocycl. Chem. 1970 7 (5) 1013.
52. Deger H.-M., Konz E., Eur. Patent 90 305.
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54. Knierzinger A., Wolfbeis O.S., J. Heterocycl. Chem. 1980 17 (25) 225.
55. Bellassoued-Fargeau M.-C., Graffe B., Sacquet M.-C., Maitte P., J. Heterocycl.
Chem. 1985 22 (3) 713.
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1995 34 (1) 51.
58. Wipfler H., Ziegler E., Wolfbeis O.S., Z. Naturforsch. B 1978 33 (9) 1016.
59. Bredereck H., Simchen G., Wagner H., Santos A.A., Liebigs Ann. Chem. 1972
766 73.
60. Wolfbeis O.S., Trummer I., Knierzinger A., Liebigs Ann. Chem. 1981 (5) 811.
61. Perez D., Bures G., Guitian E., Castedo L., J. Org. Chem. 1996 61 (5) 1650.
62. Trecourt F., Marsais F., Gundor T., Queguiner G., J. Chem. Soc. Perkin Trans. 1
1990 (9) 2409.
63. Bonnetaud B., Queguiner G., Pastour P., J. Heterocycl. Chem. 1972 9 (1) 165.
64. Dejardin J.V., Lapiere C.-L., Bull. Soc. Chim. Fr. 1978 (12) 75.
65. Dejardin J.V., Lapiere C.-L., Bull. Soc. Chim. Fr. 1978 (12) 72.
66. Van Sickle A.P., Rapoport H., J. Org. Chem. 1990 55 (3) 895.
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68. Chudgar R.J., Trivedi K.N., J. Indian Chem. Soc. 1972 49 (1) 41.
69. Narasimhan N.S., Bhagwat S.P., Synthesis 1979 (11) 903.
70. Billeret D., Blondeau D., Sliwa H., J. Heterocycl. Chem. 1993 30 (3) 671.
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(1) 175.
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81. .., .., .., 1996 66 (10) 1748.

192

InterBioScreen

2-
.., ..
.
01033, , . , 64

: 2-- 1, 3-
2 3- 3.

Het

O
Het

O
1

O
Het

O
2

, , ,
.

. ,
,
,
. ,
.
, , ,
, , , , , , , , .
2--, 3-
3-.
: , , ,
.
. "" 2- [1]. - 4,
[25]. , 2

193

4
( 1).
1
MeO

OMe

EtO
O

OMe
MeO

OMe

HO

R
OMe O

OH O

[3, 4, 6]
-,
. , - ,
[7]. -
89 [8].
- 3- [9].

, 2 , , , [1013]. -
, - , - 3585%.
[14, 15], [16, 17] . -
- 5, -
( 2). , [1820].
2
Ph

O
O

Ph

194

O
Ph

CH2

BH
5

InterBioScreen

Ph
O

OH

BH
B

Ph

, , , , ,
. ( 8085%) [18].
- 6
,
[14, 17, 21].
,
5968%. 2-: 2-- [22], 3-, 4--, 2--, 2-[2325], 5-, 6-- [26], 5- [27].
- 5
P2O5, [28],
[29].
- 5 260
[3032]. ,
(4348%) ,
. - 7 ( 3), [33] -(-)-2- 8 2-(-2-) 9, - 8 .
8 .
3

OH
Se
O

Se
O

Se

O
7

O
9

, 2

195

[3436] ,

,
, . : 2-, 6 ,
; -
6, 6- ,
- , 3-, 3-, 65-,
, 6
. ,
2- 2,6- "" . [37].
[38]
, .
.
[39, 40].

[41], -
.
, - .
, -
, , , 3--
3- [42]. 3-, , ,
[43] ( ). ,

(, , , ) [44, 45].
,
2-(2-)-3-(2-) [46].
2-(2-)- 14 2- 10 -2- 11 100
12 13
[47] ( 4).
2- [48].
,
, . - . ,
- [49], [50]
196

InterBioScreen

[51] . [52] ,
. ,
.
4

OH

Na
100C

EtO

O
R

O
11

10

12

HO

AcOH

H2SO4

O
O

13

14


16. [53].
240250 [54]
15 [5557] ( 5).
5

O
OH

(HO)n

Ph

Ph

(HO)n

EtO

O
O

15

16

17

17 - [58].
[59].
[60].
, 2

197

,
, .
-
2-(2-)- 2-(3-) 3035% [60].
,
2- ,
18 19 [61],

3- 20 [62, 63].
, ,
- [64].

OH

O
OH

18

19

20

1898 . [65] 22
18 21 ( 6).
6

OH

R
Br2

OH
Br

Br
O

O
R

18

21

22

.

[66].
[67,
68]. , [69], ,
, , , , [70].
[71].
198

InterBioScreen

,

() 23 [72, 73].
O
Ar
O
23


[74]
[75, 76], [77].
, 2'-,
[78, 79], [80], [81], 5575%.
[82]
. 5085%
2'- [83].
2'- [84]
[75]. [8591].
3- 20
18 ( 7), [92] [93].
7

OH

R
NaOH

H2O2

OH

18

20

3- , 2 [62],
[94], , , [81, 95, 96], [97].
3- 2--3-
, , : 23, 24, 2--3- 25 [98, 99].
, 2

199

OH

Ar

O Ar
24

25

OH


[100103].
, : [104], [105], [106]. .
1904 [107], 22 19 3- 26
( 8).
8
O

Ph Br
2

Ph
Br

Ph

HBr

19

26

22

N- [108]
[71]. [105].
19
27 22
73% [109] ( 9).
9
O

O
19

Ph (Ph3C)+ClO4

O
+

Ph

OH

ClO4

27

Ph

O
22

[110112]
, [()]
2- .
200

InterBioScreen

2-, , , , ,
[80, 95].
2-, . , , 2-(1--5) 29 2- 28
[113] ( 10).
10
HN N
O

CN

NaN3

O
28

29

-2-(1--5) [114, 115].


2- 30 32 - 31 33 [116]
( 11).
11

NH2

O
O

OEt

H2N

30

31

O
32

HN

O
O

N
H

H2N

(AcO)2Cu

O
33

, 2

201


4-
[117, 118]. 2- 18
70% ,
, , [119, 120] ( 12).
19 ,
4- 34 4- 35.
12
(EtO)3CH

HClO4

R'

OH
R

[CH(OEt)2] ClO4

EtOH

R'

+
(EtO)2CH ClO4

O
R
O

O
19

18

O
R

R'

+
(EtO)2CH ClO4

R'

O
+

ClO4
OEt

OEt
34

35

, [121, 122].

1.
2.
3.
4.
5.
6.
7.
202

Kostanecki S., Tambor J., Ber. Bunsen-Ges. Phys. Chem. 1895 28 2302.
Emilewicz T., Kostanecki S., Tambor J., Ber. Bunsen-Ges. Phys. Chem. 1899 32
2448.
Czaykowski J., Kostanecki S., Tambor J., Ber. Bunsen-Ges. Phys. Chem. 1900 33
1988.
Kostanecki S., Rozycki A., Tambor J., Ber. Bunsen-Ges. Phys. Chem. 1900 33
3410.
Kostanecki S., Tambor J., Ber. Bunsen-Ges. Phys. Chem. 1900 33 330.
Kostanecki S., Steuermann J., Ber. Bunsen-Ges. Phys. Chem. 1901 34 109.
Gulat K.C., Venkataraman K., J. Chem. Soc. 1936 (2) 267.
InterBioScreen

8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.

Reichel L., Henning H.-G., Ann. 1959 621 72.


Fletcher H., Philbin E.M., Thorton P.D., Wheeler T.S., Tetrahedron Lett. 1959
(6) 9.
Koninklijke Ind., Dutch Patent 70 267; Chem. bstr. 1953 47 6445h.
Wander A.-G., Brit. Patent 728 767; Chem. Abstr. 1956 50 7877b.
Schmutz J., Hirt R., Kunzle F., et al., Helv. Chim. Acta 1953 36 620.
Koo J., J. Org. Chem. 1961 26 635.
Baker W., J. Chem. Soc. 1933 (11) 1381.
Baker W., J. Chem. Soc. 1934 (12) 1953.
Mahal H.S., Venkataraman K., Curr. Sci. 1933 2 214.
Mahal H.S., Venkataraman K., J. Chem. Soc. 1934 (11) 1767.
Dayle B.G., Gogan P., Gowan J.E., et al., Sci. Proc. Roy. Dublin Soc. 1948 24 291.
Gowan J.E., Wheeler T.S., J. Chem. Soc. 1950 (7) 1925.
Schmid H., Banholzer K., Helv. Chem. Acta 1954 37 1706.
Virkar V.V., Wheeler T.S., J. Chem. Soc. 1939 (11) 1679.
Ollis W.D., Weight D., J. Chem. Soc. 1952 (10) 3826.
Devitt P.F., Timoney A., Vicars M.A., J. Org. Chem. 1961 26 4941.
Donnelly D., Geoghegan R., O'Brein C., et al., J. Med. Chem. 1965 8 (6) 872.
Thakar K.A., Deshpande G.D., J. Indian Chem. Soc. 1972 49 (10) 1029.
.., .., ,
, : , 1969, . 38.
.., .., ,
, : , 1969, . 45.
Simonis H., Z. Angew. Chem. 1926 39 1461.
Chavan J.J., Robinson R., J. Chem. Soc. 1933 (4) 368.
Dunne A.T.M., Gowan J.E., Keane J., et al., J. Chem. Soc. 1950 (4) 1252.
Lynch H.M., O'Toole T.M., Wheeler T.S., J. Chem. Soc. 1952 (6) 2063.
., , : -
, 1953, . 516.
.., .., .., 1965 1 163.
Jain A.C., Mathur S.K., Seshadri T.R., J. Sci. Ind. Research B (India) 1962 21 214.
Rama Rao A.V., Telang S.A., Nair P.M., Indian J. Chem. 1964 2 (11) 431.
Srimannarayana G., Subba Rao N.V., Indian J. Chem. 1968 6 (12) 696.
Subba Rao A.V., Subba Rao N.V., Curr. Sci. 1966 35 (6) 149.
Grover S.K., Jain A.C., Mathur S.K., Seshadri T.R., Indian J. Chem. 1963 1
(9) 382.
Recordati S.F., Ital. Patent 6 410 430; Chem. Abstr. 1965 63 9917e.
Looker J.H., Edman J.R., Dappen J.I., J. Heterocycl. Chem. 1964 1 (3) 141.
Allan J., Robinson R., J. Chem. Soc. 1924 125 2192.
Gripenberg J., in The Chem. of Flavonoid Compounds, Geissman T.A., Ed.,
London: Pergamon Press, 1962, p. 411.
Baker W., F1emons G.F., Winter R., J. Chem. Soc. 1949 (6) 1560.
Kuhn R., Low I., Ber. Bunsen-Ges. Phys. Chem. 1944 77 196.
Szell T., Dozsai L., Zarandy M., Menyharth K., Tetrahedron 1969 25 715.
Huffmann K.R., Kuhn C.E., Zweig A., J. Am. Chem. Soc. 1970 92 (3) 599.
Banerji K.D., Poddar D., J. Indian Chem. Soc. 1976 53 (11) 1119.
Thakar K.A., Muley P.R., Indian J. Chem. 1976 50 (12) 3298.

, 2

203

49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
59.
60.
61.
62.
63.
64.
65.
66.
67.
68.
69.
70.
71.
72.
73.
74.
75.
76.
77.
78.
79.
80.
81.
82.
83.
84.
85.
86.
87.
88.
89.
204

Ruhemann S., Ber. Bunsen-Ges. Phys. Chem. 1913 46 2188.


Bogert S., Marcus J., J. Am. Chem. Soc. 1919 41 83.
Gottesmann A., Ber. Bunsen-Ges. Phys. Chem. 1933 66 1168.
Seka R., Prosche G., Monatsh. Chem. 1936 69 284.
Simonis H., Remmert P., Ber. Bunsen-Ges. Phys. Chem. 1914 47 2229.
Mentzer C., Pillon D., Compt. Rend. 1952 234 444.
Pillon D., Bull. Soc. Chim. Fr. 1954 (1) 9.
Pillon D., Bull. Soc. Chim. Fr. 1955 (1) 39.
Pillon D., Massicot J., Bull. Soc. Chim. Fr. 1954 (1) 26.
Pacheco H., Gatto R., Bull. Soc. Chim. Fr. 1960 (1) 95.
Teoule R., Bull. Soc. Chim. Fr. 1959 (2) 423.
Teoule R., Grenier G., Pacheco H., Chopin J., Bull. Soc. Chim. Fr. 1961 (3) 546.
Adams J.H., J. Org. Chem. 1967 32 3992.
Limaye S.D., Limaye D.B., Rasayanam 1952 2 (2) 41; Chem. Abstr. 1953 47 4879.
Marathe K.G., J. Univ. Poona Sci. Technol. 1958 14 63; Chem. Abstr. 1960 54
3402.
Litkei Gy., Bognar R., Dinya Z., Acta Chim. Acad. Sci. Hung. 1972 71 (4) 403.
Kesselkaul L., Kostanecki S., Ber. Bunsen-Ges. Phys. Chem. 1886 29 1896.
Nadkarni D.R., Wheeler T.S., J. Chem. Soc. 1938 (11) 1320.
Tambor J., Ber. Bunsen-Ges. Phys. Chem. 1916 49 1704.
Motwani D.C., Wheeler T.S., J. Chem. Soc. 1935 (10) 1098.
Litkei Gy., Bognar R., Acta Phys. Chim. Debrecina 1971 (3) 239.
Chhaya G.S., Trivedi P.L., Jadhav G.V., J. Univ. Bombay, Sect. A 1958 27 26;
Chem. Abstr. 1960 54 8807.
Kutumbe K.R., Marathey M.G., Ber. Bunsen-Ges. Phys. Chem. 1963 96 913.
Seshadri T.R., in The Chem. of Flavonoid Compounds, Geissman T.A., Ed.,
London: Pergamon Press, 1962, p. 161.
Donnelly D.J., Donnelly J.A., Murphy J.J., et al., Chem. Commun. 1966 12 351.
Mahal H.S., Rai H.S., Venkataraman K., J. Chem. Soc. 1935 (9) 866.
Wadodkar P.N., Indian J. Chem. 1963 1 163.
., .., . , . . 1960 2 267.
Donnelly J.A., Doran H.J., Murphy J.J., Tetrahedron 1973 29 (7) 1037.
Annigeri A.C., Siddappa S., Indian J. Chem. 1964 2 (10) 413.
Annigeri A.C., Siddappa S., Monatsh. Chem. 1965 96 (2) 625.
Kumari S.S., Krishna K.S.R., Mohan Rao A.V., Subba Rao N.V., Curr. Sci. 1967
36 (16) 430.
Corvaisier A., Bull. Soc. Chim. Fr. 1962 (3) 528.
Hoshino Y., Oohinata T., Takeno N., Bull. Chem. Soc. Jpn. 1986 59 (7) 2351.
Hoshino Y., Oohinata T., Takeno N., J. Chem. Soc. Jpn. 1985 11 2104.
Doshi A.G., Soni P.A., Ghiya B.J., Indian J. Chem., Sect. B 1986 25 (7) 759.
.., .., .., 1975 (8) 1146.
.., .., .., .., . ,
. 1978 (5) 428.
.., .., .., .., . . . 1983
49 (2) 174.
.., .., .., .., 1981 (9) 1202.
.., ., . ., 1992 (7) 879.
InterBioScreen

90.
91.
92.
93.
94.

Grishko L., Turov A., Khilya V., et al., Acta Chim. Hung. 1983 112 (4) 401.
.., ., .. ., 1986 (2) 192.
Algar J., Flynn J.P., Proc. Roy. Irish Acad. B 1934 42 1.
Oyamada T., J. Chem. Soc. Jpn. 1934 55 1256.
Annigeri A.C., Siddappa S., J. Karnatak. Univ. 19641965 910 21; Chem. Abstr.
1966 64 9676h.
95. Raut K.B., Wender S.H., J. Org. Chem. 1960 25 50.
96. Corvaisier A., Tirouflet J., Compt. Rend. 1960 251 1641.
97. Venturella P., Bellino A., Piozzi F., Farmaco Ed. Sci. 1971 26 (7) 591.
98. Summins B., Donnelly D.M.X., Philbin E.M., et al., Chem. Ind. 1960 348.
99. Summins B., Donnelly D.M.X., Eades J.F., et al., Tetrahedron 1963 19 (4) 499.
100. Geissman T.A., Fukushima D.K., J. Am. Chem. Soc. 1948 70 1686.
101. Balakrishna K.J., Seshadri T.R., Viswanath G., Proc. Indian Acad. Sci. A 1949
30 120.
102. Wheeler T.S., Record Chem. Progr. 1957 18 133.
103. Simpson T.H., Whalley W.B., J. Chem. Soc 1955 (1) 166.
104. Christian .., Amin G.C., Acta Chim. Acad. Sci. Hung. 1959 21 391; hem.
bstr. 1960 54 2207.
105. Amad W.I., El.-Neweihy M.F., Selim S.F., J. Org. Chem. 1960 25 1333.
106. Reichel L., Hempel G., Ann. 1959 625 184.
107. Kostanecki S., Szabranski W., Ber. Bunsen-Ges. Phys. Chem. 1904 37 2634.
108. Nakagawa K., Tsukahima H., J. Chem. Soc. Jpn. (Nippon Kagaku Zasshi) 1954 75
485; Chem. Abstr. 1957 51 11339f.
109. Schnberg A., Schutz G., Ber. Bunsen-Ges. Phys. Chem. 1960 93 1466.
110. Singh O.V., Kapoor R.P., Tetrahedron Lett. 1990 31 (11) 1459.
111. Prakash O., Pahuja S., Synth. Commun. 1990 20 (10) 1417.
112. Takeno N., Fukushima T., Takeda S., Kishimoto K., Bull. Chem. Soc. Jpn. 1985 58
(5) 1599.
113. Augstein J., Cairns H., Hunter D., King J., Brit. Patent 2 142 527; Chem. Abstr.
1972 77 5488g.
114. Augstein J., Cairns H., Hunter D., King J., Brit. Patent 2 142 556; Chem. Abstr.
1972 77 5475h.
115. Peel M.E., Oxford Al.W., Brit. Patent 2 111 145; Chem. Abstr. 1972 76 3864q.
116. Hennart C., Fr. Patent 1 488 223; hem. bstr. 1968 69 36130f.
117. .., .., .., 1971 (8) 1112.
118. .., .., .., 1975 (4) 465.
119. .., .., 1972 8 (10) 2188.
120. .., .., .., 1976 12 432.
121. .., .., .., .., 1995 (3) 322.
122. .., .., .., 2002 (3) 306.

, 2

205


..1, ..2, ..2, ..2,
..3
1

InterBioScreen
119019, , / 218
2

450054, , . , 71
3
. ..

630090, , . . , 9


.
,
.
, .
1 2 [1].

+ S
1

S
2

. [2] [25].
in situ,
.

[6, 7].

, = ( = , , N).
1,3- , . [2] [813].
.
, , -
206

InterBioScreen

.
1985 . [10].
15
,
.
, .
1.
, -
- . 1,2- [3, 14] 2,3- [3, 1316]
.

. , ( Rh Cu) [3].
, - 3ae
4060% [17, 18].
4
.
3 1,2-, 3b c 2,3-
( 1).
1

n( )

N2

BnS

Rh2(OAc)4

OEt
O

N2

Rh2(OAc)4

R'

4be

3a

Bn
OEt

OEt

OEt
R

n( )

n( )

OEt
R

Bn

4a
n( )

n( )

O
O

n( )

S
R

R'

b R = R' = H, n = 2; c R = R' = Me, n = 1;


d R = Ph, R' = H, n = 2; e R = Me, R' = H, n = 2

, 2

OEt
O

R'
3be

207

1,3- 5 1,2- 1,2- 6, S-S [19].


, 6
-S. 7
8 ( 2).
2

R
1
R

3
4

R
5
R

N2CR62

h .

S S

3
4

R
5
R

S S

3
4

R
5
R

S
R

R
R

:S
S

R
R

R6

R
R

S
S

R62C=S

R
S

3--4- 9
2,3- 10,
11
[20] ( 3).
3
O
N2

[Rh]

S
11

208

O
~2,3

S
10

InterBioScreen


, 2,3-
, [15, 21].
, -4,7- 12,
13,
14 [2224]. 15,
16, 17,
18. 2,3- 18 (Z)- 13 ( 4).
4

RO

RO

RO
b

a
+

OTf
O

S
O

OEt

OEt
14

15

16

OR
O

OR

OR

c
+

OEt

O
Et

18

17 (36%)

O
OR

OH

...

O
HO

Et
12 (89%)

Tf = F3CSO2

Et

O
13

a - TfOCH2CO2Et; b - K2CO3; c - TfOCHMeCOEt, K2CO3

2,3-C , [6,3,1]--3- 19,


[25, 26].
, 2

209

20. 21, 22
( 5).
5
SiMe3
I

Ph
Ac

MeCN

OAc S

70C

AcO

K2CO3

O
O

20

22

SiMe3

S+

AcO

OAc

Ph
O

Ac

21

O
O

19 (65%)

23, 24 ,
[27, 28]. 25
CuSO4 26, 2,3- 23 24 4 : 1
( 6).
6

O
S
( )8
25

R'

S
S

~ 2,3

( )8
26

R
S
( )8
23

O R'

R'
O

R
S

8( )

S
24

a - N2C(R)CO2R', CuSO4,

210

InterBioScreen

27ab, 28 2,3- 29ac,


30ac [29].
. 29a, b
27a, b,
1,3- 28 ( 7).
7

OEt

DBU

S+
OTf

R = Me, Bu

OEt

27ab

OEt

OEt

Ph
28

29ac

30ac

R = Ph

R = Me (a), Bu (b), Ph (c)

31, 32, 3- 7,8--5,13[c,f] 33 [30] ( 8).


8

OTf

S+

CH2

SiMe3

32

31

33

a - CsF, DBU, , 20C;


R = H, Me, OMe, CF3

34 -,
[4,5] 35 [31].
34 36, 2,3- 35.
35 37,
38a, b ( 9).
, 2

211

O
a
S

CN

N
O

CN

34
b

N
H

CH2

CN
36

CN

NC
37

EtO2C
EtO2C

EtO2C
35

EtO2C

S
CN

CN

38b

38a
aO

, ; b - 205C; c - EtO2CHC=CHCO2Et
O

N
H

1- 34
39 40 (~1 : 1) 75% [31].
41, . S- ( ), 42,
2,3- 39.

- 43,
40 ( 10).
10

CN
34

212

R'

S+
NC

R'

41

InterBioScreen

NC
R

CH2
R'

R'

NC

39

42

NC

R'
R

NC

43

R'

40

R = H, R' = CO2Me; R = R' = CO2Me

44 45 ( 31%) [32]. 45
46 (4) (10)-S ( ).
45 1,5-, 47 95%.
46b
2,3- , 1,2-
48 ( b) ( 11).
11

EC CE
S

CN
44a, b

PhH

NC
E

S R

R
E

NC
E

46a, b

, 2

213

CN

R=H

200C

E
E

NC

45

E
47

R = Me

NC
E

48
R = H, Me; E = CO2Me, CO2Et

,
. , , , 1,3- 1,5-.
, , - .
: 1,3-
1,3,4- [33];
[34]; [35];

[36]. , 49 50 1,5-
( 12),
51 52, 53 [37].
12
Ph

R
CN

S
Ph

O
52

214

N2

CN
R

Ph
CN

51

Rh2(OAc)4

O
49 (83%)

InterBioScreen

Ph
S

R
CN

S
51
Rh2(OAc)4

53

50 (66%)
R = 4-ClC6H4


1,3- . 5456 [38].
57 58,
59 ( 13).
13
O

O
S

R
S

CH2N2
70C

N N

N2

58

59

OMe

54

R
O
CO2Et

EtO2C

NC
EtO2C
O
O

S
O
S

CN

57

CO2Me

NC

S
S

R
S
CN
CO2Et

55

RO
O

56

O
60 1,3- 61
62 [39] ( 14).
, 2

215

14

O
CO2Me

MeO

CH2
S+

S
60
S
R

R R

61ac

R2C = Ph2C (a),

R
R

62ae

(b),

(c),
S

(d), O

(e)

1,3-
63 1,3- 64 -5(4)- 65 [40] ( 15).
15
R"
S

R'
N
R'"
R'
R"

N
R'"

R"
S

R'

+
R2C S CH2
64ac

R2C=Ph2C (a), O

216

(b),

63b

R"
S

R'

R'"

O
S

R'"

65

63a

S
S
Ph Ph

63c

S
(c)

InterBioScreen

2.
66 ()- 67a, ()- 67b
()- 68
69 [41, 42]. 70 1,2-
66 ( 16).
16

S Ph

Ph

OEt
N2

Rh2(OAc)4

O
OEt

O
69

70

H R R'
...
Ph S

O 67a, b

OEt
N
O

66

H
...
a R = CH2OH, R' = H;
b R = H, R' = CH2OH

OH

N
O 68

[43] 71a, b
, ,
72a, b 73a, b. ,
.
(Rh2(Cap)4) , 2,3-
72a, b.
(Rh2(OAc)4, Cu(acac)2, Cu(OTf)2, Pd(OAc)2) 73a, b ( 17).
, 2

217

H
N

17

Ph
H
.

N2
71a

Ph

N
O

O
Ph

Ph

72a

73a

S
H

H
.

N2

Ph

N
O

O
72b

71b

Ph

73b

1,2-
[14]. ,
, -
- . , - 74
6-
[44]. 76 75, 74 -
( 18).
18
H

O
N
R

Bn

N2
O

N
S

OR

N
+

N
R

Bn

76

O
OR

75

Bn
N
O
O

N
R

H S

OR

74 (72%)

R = 4-NO2C6H4

218

InterBioScreen

, ,
(+)- 77a
(+)- 77b [45]. 78,
(S)- , -
79, 1,2- . ,
C-S 80.
=N
( 19), 2,3-- 81,
77a, b ( 19).
19

Ph

BnO2C

TBSO

O
O

N2C(CO2Bn)2

CO2Bn

S Ph
+

TBSO

78

79

CO2Bn

S
N

CO2Bn

Rh2(OAc)4

O Ph

BnO2C
BnO2C
H

Ph
S
N

...

TBSO

TBSO
80

81 (82.6%)

HO
H
R"
R'

77a, b

a R' = H, R" = OH; b R' = OH, R" = H;


TBS - t-BuMe2Si

[46, 47] .
- 82a, b
- 83a, b.
4- 84a
5- 84b, 85a, b. 84a, b
- [48] ( 20).
, 2

219

20

CO2Bn

n( )

O
O
2+
S

Boc

CO2Bn
( )n

NH
Boc

82a, b

83a, b

..

CO2Bn

( )n

( )n

NH

Boc

CO2Bn

Boc

85a, b

84a, b

Boc = t-BuOCO; n = 1 (a), 2 (b);


a - Me2SOCH2, , 20C (97%); b - [Rh2+]

,
, [4956]. N--- 86 - 87 [57, 58]
, .
88 89,
, [53]. - 90 91 ( 21).
,
.
21
O

OH
R
O

O
N

a, b,
c, d, e

S+
O
f

R
N

PhCO2Me

S
86

88

90

R = H, Me, i-Pr, Bn

220

InterBioScreen

OH

a, b,
c, d, e

+
S

O
O

f
PhCO2Me

O
S

89

87

91

a - SO2Cl2; b - CH2N2; c - HBr; d - Me2S; e - NaOHK2CO3; f - PhCO2H, 110C

, - -,
[53], , [54].
92, 93 - -2,3- [55] -2,3- [56] , -
94, 95 [55, 56] ( 22).
22

O
N

S+

O
N

93

N
94 (58%)

92

S+
O

O
S

95 (60%)


[5963]. , 96
97, 98. 99
( 23), 100 [59].
, 2

221

23

N2

S
96

97

SH

Rh2(OAc)4

Ni/Re

98

99

100

101
102 [60, 61] ( 24).
24

N2
O

S
Rh2(OAc)4

SH

OH

...

101

102

103, 104, N--1,2-, 105, 106


107 [62] 108
[63]. ( 25), .
222

InterBioScreen

25
O

S
N

O
O

O
N

Ph

Rh2(OAc)4

O
N

Ph

105

103

...

N
O

O HO

107

S
N
O

O
N

Ph

Rh2(OAc)4

O
N

N
Ph

104

...

106

O
N
O

H
HO
108


[64]. 109
110 111
, 2

223

112 (+)- ( 26).


26
OH

Cl

O Rh (OAc)
2
4

NHTs

PhH

N2
S Ph

O
S Ph

109 (91%)

S Ph

Ph
S

O
O

112 (56%)

111

110

Ph

-, 113 114 ( 27)


2,3- 115, 116, [6568].
27

OR

RO

O
Rh2(OAc)4

Ph N2
S

( )n

Ph +S

Ph S

O
( )n

O
n( ) O

115

113

RO
N2

OR

OR

Rh2(OAc)4

( )n

S Ph
116

Ph

OR
O

Ph S
O
( )n

O
( )n
114

R = Me, Et; n = 1, 2

224

InterBioScreen

117 ( 28),
, [2,3-b] 118 [67].
28

Ph

...

S
EtO

O
O
H

O
117

118


- 119 [69] - 120 [70],
-. 2,3-
121, 122 ( 29).
29
O

EtO

Ph
O

N2

n( )

S Ph

n( )

R
EtO

119

121

R = H, Me; n = 1, 2

S
OEt

n( )

OR'
O
N2

O
Ph

Ph
S

S
Rh2(OAc)4

( )n

PhH,

R, R' = Alk; n = 1, 2

( )n

OR'
O

R
122

Ph

OR'
O
O

n( )

R
120

, 2

225

2,5-
123 [71]. , -4--2- 124, N- 125
126. 2,5- 123 ( 30).
- 124 .
30

BPh4

Ph
NTs
125

OH
124

KOH, MeCN
20C, 7

NHTs

Ph

Ph

N HO

Ts

Ts

126

Ph

123 (52%, anti : syn = 2 : 1)


2,3-
, ,
.
, 127 - 128,
129 [72].
, 2- 127 (n = 3)
129 ( 31).
31

( )n
S

( )n


MeOH, 20C

S
NTs

128ac
127ac
a n = 1, (55%); b n = 2, (54%); c n = 3, (61%)

226

( )n

~2, 3

N S
Ts
129ac

InterBioScreen

130 131
1,2- 132 3,4- 133 [72] ( 32).
32

~2, 3
+

MeOH, 20C

S
NTs

140C

S N
Ts
132 (55%)

130 (70%)

S
N Ts

~2, 3

S 140C
NTs

MeOH, 20C

131 (83%)

133 (57%)

2,3- 134 N 135.


136 137 [31].
, , , R = H
, [4,5] 35 ( 33).
33

HCl

S
CH2
R CN
134

NH

136

N
R
135

AcOH

NH
R
R = Me, Cl, Br

137

OAc

138
139 [73].
2,3-
140 ( 34), 138 .
, 2

227

34

O
S

H
N

Ph

Ph

N
H

138

S
+

S
CH2
Ph

Ph

O
Ph

140

139

1,4- 141 2,5- 142


[74, 75].
143 2,3- ,
144. , , 2
5 ( 35), .
35

[Rh], R'CN2COR"

Cl

Cl

Cl
+

S
R

R'

60100C

R"
Cl O
143

142

R
R

Cl

O
R"

S
R'

Cl

Cl

Cl
S

O
R"

R'

144

145

R = H, Cl; R' = CO2Et, CO2Bu-t, Ts;


R" = Me; R'+R" = COCH2CMe2CH2

228

InterBioScreen

145d, 2,3-
146, [76, 77].
L- 147 (Z- 147, E- 147)
146
,
148 (Z- 148, E- 148). 145d. 148
( 36).
36

i- Pr

O
S

[Rh]

O
N2

i- Pr

147

i- Pr
S

HBF4.Et2O

146

DBU

O 78C

BF4
148

i- Pr
S

i- Pr

+
O

145a

1. Z- 147
2. E- 147
3. Z- 148
4. E- 148

Rh2+
Rh2+
DBU
DBU

i- Pr

+
O

O
145c

145b

35%
28%
66%
64%

i- Pr

145a
84
10
94
4

145b
8
83
4
93

O
O

145d

145c
7
2
2
1

145d
1
5

[78] 3,4--1,3--4(2) 149 1,2- 150, -3(2)- 151


. 1,2 , S-N ( 37).
, 2

229

37

N2C(CO2Et)2

N Et
S

+ N

Rh2(OAc)4

~1,2

Et

EtO2C CO2Et
151

Et

CO2Et
CO2Et

149 (70%)

150

152
153 ( 38), 154 [79].
38

OTf4

SiMe3
+

CH2
S

CsF, DBU
, 20C

R'

R'

R'

153

154

152

R, R' = H, Me, OMe, CF3

155, in situ
156 Cu(acac)2, 157 [80] ( 39).
39

IPh
O
156

O
CS2
Cu(acac)2

O
155

S
S

S
O
157 (85%)

-- 158 159, 2--1,3-


160 [81] ( 40).
230

InterBioScreen

40

MeO

S
t- Bu

N2C(CO2Me)2

Bu -t

Rh2(OAc)4

MeO
O

OMe
t- Bu

OMe

Bu -t

t- Bu

158

Bu -t
159

O
MeO
MeO

Bu -t

Bu -t

O
160

161
( 41), [82], 1,6--3,9-[4,4]-2- 162.
41
O
N

S
S H
N
Ph

N
S

OMe
OMe

N
Ph

OMe
OMe
O

O
161

162

163 164 [83].


165 2--4-[3,1,1]-2-
166 ( 42).
,
.
, 2

231

42

CH2

S
R

NH2

164

S
HN

163

165

OH

166 (64%)

R = Me, Ph

,
. ,


,
. , ,

. ,
,
, .


, . 1
,
WDA, DERWENT-2000 [84],
.
1.

O O
S
O

N
S

Antibacterial,
immunosuppressive,
+ cytostatic,
K antianemic

CytochromeThiethazole
P450-inhibitor,
antioxidant

[85]

N
H

232

InterBioScreen

1.
OH

Osteopathic

Mepitiostane,
Epitiostanol

[86]

H
H

HO
O

S
NH2

H
O

[87]

Antiulcer

Gastricsecretioninhibitor

WD-94013318

[88]

Anticonvulsant,
nootropic,
antidepressant,
tranquilizer,
analgesic,
antiparkinsonic

Gabaminergic

WD-97010381

[89]

Anti-HIV

HIV-proteaseinhibitor

WD-98011946

[90]

Analgesic,
neuroprotective

Opioid-Mu

WD-98004406

[91]

O
OH

Ph

Ph

O
HO

O
OH

Ph

H
S

LY379268,
LY389795

OH

NH2

HO

Glutamateagonist-2,
Glutamateagonist-3

OH
O

Neuroprotective, cerebroprotective

NH2

: Derwent WDA

, 2

233

1.
O
N
HO

HH

Endocrine,
antilipemic,
cytostatic,
vasotropic

Estrogenantagonist

WD-98004113

[92]

Nootropic,
neuroprotecttive

Amyloidproteinantagonist-

WD-99006545

[93]

Antiserotonin-2

WD-97000100

[94]

Cytoprotectant,
hypotensive,
antiasthmatic,
tranquilizer,
neuroprotective, anti-HIV,
antacid, antiinflammatory,
antiulcer,
nephrotropic

Antioxidant,
nitric-oxide
antagonist

WD-2000007640

[95]

Antidiabetic

Dipeptidylpeptidaseinhibitor-IV

WD-2000011473

[96]

Nootropic

Vasopressinagonist

ZTTA-1

[97]

S
H

Cl
S
S

OH
F

S
O O

OH

S
S

OH

H
N

Cardiovascular,
cerebroprotective, cardiant,
vasotropic,
antiarrhythO
mic, antiarteriosclerotic,
hypotensive,
antiinflamatory

S
S

O
N
S

O
Ph

O
N
S

234

MeO

OMe

N
S

InterBioScreen

1.
O
H

N
H

Hypotensive,
diuretic

ACE-inhibitor,
neutralendopeptidaseinhibitor

ER-32935

[98]

NH2

Anticoagulant

Thrombininhibitor

WD-97012035

[99]

Immunosuppressive

Tyrosinekinaseinhibitor

WD-98011590

[100]

Cardiovascular,
inotropic

Calciumantagonist

Ho-7

[101]

Endocrine-Gen.

Tyrosinekinaseinhibitor

WD-97001705

[102]

OH

SH

HN
H

NH

S
N
Ph

N
H

N
O

O
N

S
O

OMe

Ph

MeO

OMe

S
O
S

N
N
H

O
N
S

, 2

235

1.
O
O

Cytostatic

NADHoxidaseinhibitor

WD-98012067

[103]

Antiarthritic

Interleukin1--inhibitor

WD-94002888

[104]

Vasotropic,
antiinfertility,
antidepressant,
anticonvulsant,
hypotensive,
cerebroprotective, hemostatic, cardiant,
sedative

Neuropeptidea-antagonist-Y5

WD-2000013369

[105]

Antibacterial

Proteinsynthesisinhibitor

PNU177780,
PNU176797

[106]

Antilipemic,
antiarteriosclerotic

MTP-inhibitor,
VLDLantagonist

WD-99016459

[107]

N
N

N
H

Cl

O
N

H
N

N
S

HN
R

O
S

NH
O

F
+

O
S
N
H

236

OH
O

InterBioScreen

1.
H

O O
S
N

Elastaseinhibitor

PNU156575

[108]

Cardiant,
hypotensive

Vasopeptidase-inhibitor

BMS198433,
BMS253653

[109]

Anti-HIV

HIV-Proteaseinhibitor-1

GS-4234,
GS-4263

[110]

Antidiabetic

Hypoglycemic

Kotalanol

[111]

Anti-inflammatory

OH
O

O
S H

O
HS

N
H

Ph

N
O
HO

NH2

O
S O

O
O
O

O
NH2

OH

OH

HO
S

OH

O
O S O
O HO

OH
OH
OH

, 2

237


1.

27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.

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InterBioScreen

2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.

41.
42.
43.
44.
45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
59.
60.
61.
62.
63.
64.
65.
66.
67.
68.
69.
70.
71.
72.
73.
74.
75.
76.
77.
78.
79.

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Pharmacol. Soc., Kyoto, 1994, P-645.
98. Matsuoka T., Saito M., Mori N., et al., Jpn. J. Pharmacol. 1996 71 (Suppl. 1) 146.
99. Tarazi M., DiMaio J., Siddiqui M.A., Proc. 214th Am. Chem. Soc. National
Meeting, Las Vegas, 1997, poster MEDI 052.
100. Tu N.P., Madar D.J., BaMaung N.Y., et al., Proc. 216th Am. Chem. Soc. National
Meeting, Boston, 1998, poster MEDI 261.
101. Studenik C., Lemmens-Gruber R., Heistracher P., Gen. Pharmacol. 1999 33 (4) 319.
102. Sawyer T.K., Proc. II Winter Conference on Medicinal and Bioorganic Chemistry,
Steamboat Springs, Colorado (USA), 1997, L-30.01.97.
103. Alonso M., Manu M., Arteaga C., et al., Proc. XV Int. Symp. on Medicinal
Chemistry, Edinburgh (Scotland), 1998, P344.
104. Miller W.H., Pinto D.J.P., McHugh R.J.Jr., et al., Bioorg. Med. Chem. Lett. 1994 4
(6) 843.
105. Marzabadi M.R., Wong W.C., Noble S.A., US Patent 6 124 331, 2000.
106. Friis J.M., Shobe E.M., Palandra J., et al., Proc. 39th Int. Conf. on Antimicrobial
Agents and Chemotherapy, San-Francisco, 1999, poster F-569.
107. Yanagita T., Anno T., World Patent 61 015, 1999.
108. Bissolino P., Alpegiani M., Corigli R., et al., Proc. XIV Int. Symp. on Medicinal
Chemistry, Maastricht (Netherlands), 1996, poster 5.10.
109. Cohen M.B., Kostis J., Klapholz M., et al., Proc. 101st Annual Meeting of the
American Society for Clinical Pharmacology and Therapeutics, Century City, Los
Angeles, 2000, PI-23.
110. Cherrington J.M., Mulato A.S., Fuller M.D., et al., Proc. 36th Int. Conf. on
Antimicrobial Agents and Chemotherapy, New Orleans, 1996, poster I3.
111. Jpn. Patent 086 653, 2000.
240

InterBioScreen


.., ..

614051, , / 8519

() (1: AE)
, -, .
,
"" , 1-1,3- 2.

.

OH
O

R
O

R
HO

1D

OH
O

1B

OH
O

X
OH

1A

1C

OH
X
R

O
O
1E

OH

2
1

R
2

R = Alk, -Alk, ArCH(Hal)CH(Hal), ArCH=CH, ArCOCH2, Ar, C6F5, Het .;


X = H, Hal

1
(R = Ar) , , , , , [1, 2]. , 1 (R = Ar) 5--2,3--2,3-
(3: R = Ar) [36].

2- [7]
, 2

241

. [1, 2] ( 2-4--2-) 1 - . ,
, [7].
, , , , , , ,
1,4-, 1,4- ( -), 1,2,4-, [2,3-b]1,4-, [1,4][4,3-a], [e]-1,4-
. - ,
, .
-

-
. ,
, 1 -
O-.
1ad (a R = Alk, b PhCH=CH, c Ar, d Het, X = H)
[2, 3, 810], [1114],
[12], [2, 3, 11, 1420] [20] 5- 2,3--2,3- 3 ( 1),
[3, 5, 6, 14]. 5--2,3-2,3- 3 (R = Ar, X = H) "
" [6, 20] 2,3- . .. (19341998),
,
[21, 22]. " " [23, 24] 4--5--2,3-2,3- 3 (R = Ph, X = PhCO),
[4, 23].
5--
5---2,3--2,3- 3 (R = Me, t-Bu; X = H) [12]. 5,5--3-(2,2-)-2,4- 1 (R = t-Bu, X = COBu-t),
2,2,6,6--3,5- ,
5---4--2,3--2,3- 3 (R = t-Bu,
X = COBu-t) [25] ( 1).
4- -2,3- 3 (X = Hal), 4
3 (X = H) [3, 6, 26], 242

InterBioScreen

-- 1 (X = Hal) [17] ( 1). 1, , 1e (R = C6F5, X = H)


5,6,7,8--2- 4 [1, 2, 27]. ,
6--2,4,6- 1f (R = ArCOCH2, X = H)
6--4--4H--2- 5 [28, 29] ( 1), [28].
1

O
R

O
R

OH
O

OH
O

1ad
R = Alk (a), PhCH=CH (b), Ar (c), Het (d)

X=H
H2O

X
R

O
Ph

Ph

Cl

Cl

HCl

X = PhCO

OH
O

O
3

O
Ar

N Y

Ac2O
H2O

Ar

6
Y = Ar, Het, Ph2C=N

OH
O

t- Bu

O O
O
t-Bu

Cl

Bu -t

O
[H2O] O
OH

Cl t- Bu

Cl

t-Bu

O
O 70C

t- Bu t-Bu

H2O

O
1 (R = t-Bu;
X = COBu-t)

, 2

t- Bu

O
O
O
3 (R = t-Bu;
X = COBu-t)

243

OH

Hal O
R

Hal

OH
O

R
HO

1 (X = Hal; R = Ar,
t-Bu, PhCH=CH)

O
OH
O

O
R

1e (X = H;
R = C6F5)

OH
O

O
F

O
Ar

NH3
(Et3N)

1ac, e

Hal
H2O

3 (X = Hal)

HHal
Hal2 (Hal = Br, Cl)
1ac (X = H)

1f (X = H; R = ArCOCH2)

OH

AcOH
(H2SO4)
H2O

Ar

O
5

O
OH


2- 2- 4--4-2- (6: R = Ar; Y = Ar, Het, Ph2C=N)
5--3--2,3--2- 7 [3033] ( 1).
4-
C(2) 6, 2- [33], ,
, Y [30, 31].
, 7
,
[31, 32] , ,
-3,4- [30].
6
. , 4--2[2-(1-)]-4--2- 6 (R = Ar,
Y = 2-Ph2C(OH)C6H4) [e]-1,4--3- 8 [3438]. 2- 6 (R = Ar, Y = OH),
[39], -3- (9: R = Ar, X = OH) [2]. 9
(R = Alk, Ar, X = OH, NHNH2) .

O- O,N- 1 - 6, , . S- .
244

InterBioScreen

Ph Ph
O

N
O

O
O

N
Ac

R 9
R = Ar, Alk;
X = OH, NHNH2

Ar

1c (R = Ar, X = H), -2,5- 10 11 [24, 4043] ( 2).


10 5-2,3--2,3- 3 (R = Ar, X = H) . 11 1c [24, 4043].
2

OH
Ar

O
O

Ar
HO

H2O

Ar

Ar
OH

O
O
11

OH

1c

+
H3O

Ar

O
OH
O
Ar
OH

Ar
OH

O
H

O
O

HO

OH
O

Ar

Ar

OH

O
H2O

HO

O
OH

OH

Ar

O
O

OH
O

Ar

OH

O
Ar

10


1a (R = Alk, X = H) . 12
[44, 45] [2,2,2] [46],
3--4--5--2-(2-)-2,5-2- 13 [4446] 14 [44, 45] ( 3).
, 2

245

3
OMe

OMe
O
O

12

[HO ]

12

O
O

+
[H ]

O H
13

OMe

MeO

O
OMe

HO
O
O
14

, 1, 2- 6 2,3--2,3- 3
,
[2, 3, 5, 6, 10, 14, 17, 20, 24, 3032, 36, 38, 4750].

,
.
-, -
,
. 1 - .
O-
. ,
1c (R = Ph, X = H) -2,7-, 6--1--9--1H--7- [51].
C-
C-.
CH-, ,
, .
, 1c (R = Ar, X = H) , 2- 5--2,3-2-
, 15 16,
[2, 52, 53].
246

InterBioScreen

Ar

Ar

O
O
O

O
O

O
Ar

15

16

, 1c
5--2,3--2,3- 3
(R = Ar, X = H), CH-, 3- 15 16. 3
[18, 54, 55]. , , 1
, 3,

3,4--6--2,4- 17 [55, 56] ( 4). ,
C=C-
, . , ,
16 - 2-(3--5--2,3--2-)-5--2,3--3- 18 [23] ( 4).
6 C- .
4

O
R

OH Ac2O
O

CN

Ac2O
H2O

H2O

O X

1a, c

OH
CN
OH

R
H2O

X
O

O
O

NH2

17

Et3N

O
R

3
R = Ar, t-Bu; X = CO2Et; CN

, 2

247

Cl

Ph

Ph

Cl

HCl

O
O

Ph

Ar

18

Ar
16

O,N S,N- .
[2]. , [2] .
O,N-
O,N-
-, -
1be (R = PhCH=CH, Ar, Het, C6F5; X = H) [2, 39],
2- [2, 27, 5759], - [2, 10, 17, 6068], 2--3- [66], 2- [2, 69, 70] - ( ) [2, 3438].
-3- 9 (X = OH), 3(2)--1,4--2(3)- 19 20, 7,8,9,10--1,2--1,4-[4,3-a]4,6- 21, 3--3,4--1,4--2- 22 (R = PhCH=CH,
Ar, Het; R' = H, NO2, R'' = H), 3--3,4--2H-[2,3-b]-1,4-2- 23 4--3,4--1H,5H-[e]-1,4-3- 8 24.

H
N
O

H
N
O

Ar

R'

H
N

R''

O
19
R = Ar, C6F5

22
R = t-Bu, PhCH=CH,
Ar, Het; R', R" = H, NO2

21

20

O
O
N

N
H

23
R = Ar, Het

248

H
N

Ar
O
O

R
24

InterBioScreen

, ,
22 [1, 2]. O,N- 22 24
[6365, 70, 71].
1a, c -
3- 1,4--2- 22 (R = t-Bu, Ar; R' R'' = H,
NO2), ,
[72, 73]. [14, 74] 22
-
C(3)=N(4), [75]
(. [2]). 1,4--2- 22
3--1,2,3,4--2-
- [7, 61, 73, 76]. , [2], ,
[61].
, -3- 9 (R = Me,
X = NHNH2) [77]. 22 [5, 14, 47, 67, 7274, 7880].
[5, 14, 47, 7274, 79, 80],
[5, 14, 47, 73], [5, 73, 75, 80] .
[2,3-b]-1,4--2- 23 [e]-1,4--3- 24
[2, 66, 69].
O,N-
1c (R = Ar) ,
N- 25, 3--5--1,2,4- 26 [81] ( 5).
26 [81].
5

O
Ar

OH
O

Ar

OH
NH2

O
Ar
O

H2O

OH

N
N
H

OH
Ar
H2O

25

O
N
Ar

Ar

O N

HO
26

, 2

249

S,N-
S,N- 1,4-. , - 1 (R = 4-MeOC6H4,
X = H) 2-, ,
, 6 (Y = 4-MeOC6H4),
3-(4-)-2,3,5,6--4H-1,4--2- [2, 82].
[2] ,
1c - 27,
, 2--3,4--2H-1,4--3- 28
[83, 84]. , [85, 86],
4--2-(-)-4--2- 6 (Y = 2-HSC6H4), .
28
5--2,3--2,3- 3 (R = Ar, X = H) - [3, 84, 87] . ,
28 O,S-
2--2--3,4--2H-1,4--3- 29 (
29A 29B), 1,4--2,3- 30 [85, 86] ( 6).

6
OH
Ar

O
Ac2O

O
O

H2O

H
N

O 27
O

Ar 3

1c

O
OH

H
N
S

O
Ar

29A

H2O

OH
O

HS

H
N

Ar
X

28

OH

HO
Ar

27

Ar
29B

H
N

30

250

InterBioScreen

OH
Ar

OEt
O

NH2

H2NCOCH2CO2Et
27

17

(X = H,
COPh)

Ph
O

O
O

H
N

Ar

O
X

28

Ph
O

Ar

Ar
O

H
O

O
27

O
O
Ar

32A

Ar

Ar

O
H

H2O,
ArCOMe

32B
27 =

H
N

Ar

S
S

NH2

31B

31A

SH

28
- 3,4--2--6--2,4- 17 (R = Ar, X = CO2Et) [88, 89] 4--5--2,3--2,3- 3 (R = Ph, X = PhCO) [24, 85, 86, 88, 9092]. ,
28 3--2,3--4H-1,4--2- 31 ( 31A 31B)
1,6--3,4--2,4--1,6-
(32A, B) - [88, 89, 93, 94] ( 6). 28 31 [89, 90, 9395]. 28 [92].
6 O,N- S,N-
.

1
1c (R = Ar)
, 2

251

5--2,3--2,3- 3 (R = Ar, X = H),


2,6--2--1,3--4- 33 [9698] ( 7). 1c (R = Ar) 3--4,5--1H--4,5-
34 [6] ..
4-- 2,3--2,3- 35 [6] ( 7).
- 1c, d (R = Ar, Het) 2,3--2- 36 [99] ( 7).
, S- .
7
O
O
Ar 3

Ar

OH
H

CO, CO2

O
O

Ar

1c

33

32

N N

Ph

Ph

24C

OH
O

1c, d

O
36

[O]

Ar

H2O

O
R

R = Ar, Het

OH

O
OH

N
N
Ar

Ar

Ar

34



- , ,
, . , ,
O- S-.
252

InterBioScreen


1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.

.., .., .., 1999 68 (3) 227.


.., .., .., ..,
2001 70 (11) 1039.
.., .., . 2,3, : -, 1994, . 5; Chem. Abstr. 1996
125 195292b.
., . 2,3-, :
-, 1994, . 55.
.., 2001 (3) 291.
.., . : .
100- .. , .: , 2001, . 133.
.., .., .
, . .., .: IBS PRESS, 2003,
. 1, . 255.
.., .., .., .., . .
476 254, . . 1975 (25) 71; . 1977 679.
.., .., .. ., 1975 (11) 1468.
..,
, : -, 1989.
Kozminykh V.O., Igidov N.M., Kozminykh E.N., Aliev Z.G., Pharmazie 1993 48
(2) 99.
Kappe C.O., Kollenz G., Wentrup C., Heterocycles 1994 38 (4) 779.
.., .., .., . . 1 727 378,
. . 1996 (3) 321; Chem. Abstr. 1997 126 (5) P59851b.
.., . - . , : . ., 1999.
.., .., .. ., -, ,
1997, . 14, . 24.09.97, 2906-97; . 1998 4156.
.., .., .., ..,
1997 33 (8) 1192.
.., . . . , : -, 1997.
.., .., O.A. ., 1999 (11) 1466.
.., .., 2000 70 (11) 1890.
.., .., .. ., 2001 37 (7) 1067.
.
, : , 1997, . 72.
(19162001). , : -, 2001, . 280.
.., .., .. ., 2001 37
(1) 126.
.., . . . , : . ., 2002.
Kollenz G., Kappe C.O., Nabey H.A., Heterocycles 1991 32 (4) 669.
.., .., .., 1984 20 (8) 1749.
Saloutin V.I., Skryabina Z.E., Bazyl' I.T., et al., J. Fluor. Chem. 1994 69 119.
Clark B.P., Ross W.J., Todd A., 2 123 813; .
1984 2312.

, 2

253

29. Stiles M., Selegue J.P., J. Org. Chem. 1991 56 (12) 4067.
30. .., .., . . .-. .,
. 85- "
: ", :
. ., 2001, . 57.
31. .., .., .., .
, . .., .., .: -, 2001,
. 2, . 257.
32. .., .., .., .., . . "
", : -, 2001, . 1, . 171.
33. .., .., 2001 (8) 1130.
34. .., .., .. ., .
, : -, 1996, . 128.
35. .., .., . . . "
", : -,
1996, . 1, . 37.
36. .., .., .., .., .
-
: . , .: , 1997, . 36, . 2, . 8.
37. .., .., .., .., . ,
. . 1998 (11) 2317.
38. .., .., .. ., .-. .
1998 32 (9) 32.
39. Salvatori S., Gazz. Chim. Ital. 1891 21 (2) 286.
40. .., .., .. ., .
. .-. . "
: ", : . .,
2000, . 78.
41. .., .., .. ., . . 1 . .. , : , 2000, . 415.
42. .., .., .., ..,
. . LVIII-LIX . . "
", : . ., 2001,
. 5, . 11.
43. .., .., .., ..,
. . . -. "
", : , 2001, . 263.
44. Scarpati M.L., Trogolo C., Javarone C., Gazz. Chim. Ital. 1969 99 (11) 1167;
. 1970 13143.
45. Berner E., Kolsaker P., Acta Chem. Scand. 1969 23 (2) 597; . 1969
23260.
46. Lee H.J., Kim T.Y., Kim J.N., Synth. Commun. 1999 29 (24) 4375.
47. .., .., .. ., . . .
. . " ", ., ,
1999, . 106.
254

InterBioScreen

48. .., .., .. .,


. ., 95- . ..
" , ", : ,
2000, . 2, . 48.
49. .., . . . "
", : -, 2001, . 1, . 158.
50. .., .., . .-. .
" :
", : . ., 2002, . 25.
51. Cooke R.G., Merrett B.K., O'Loughlin G.J., Pietersz G.A., Austral. J. Chem. 1980
33 (10) 2317; . 1981 13183.
52. Chovin P., Ann. Chim. 1938 9 (11) 447; Chem. Abstr. 1938 32 74359.
53. Klingsberg E., Chem. Rev. 1954 54 59.
54. Kozminykh V.O., Konshina L.O., Igidov N.M., J. Prakt. Chem. (Chem.-Ztg.) 1993
335 (8) 714; Chem. Abstr. 1994 120 (15) 191238n.
55. .., .., .., 2001 37 (11) 1604.
56. .., .., .., . . V .
-. , : , 2002, . 199.
57. .., .., .. ., . , . . 1994 (2) 299.
58. .., .., .. ., . . 621 676,
. . 1978 (32) 74; Chem. Abstr. 1979 90 87478.
59. .., .., .., . . 910 627,
. . 1982 (9) 64; Chem. Abstr. 1982 97 92298.
60. .., .., .., 1979 15 (3) 520.
61. .., .., .., 1979 15 (4) 847.
62. .., .., .., .., . , . .
2000 (12) 2080.
63. .., .., .., .., . .
. , : ,
2000, . 155.
64. .., .., .., 2001 37 (4) 630.
65. .., .., .., ..,
. . .-. . "
: ", : . .,
2000, . 62.
66. .., .., .. ., .-. .
2002 36 (2) 33.
67. .., .., .. ., . . V
. -. , : ,
2002, . 188.
68. .., . . . , : . ., 2002.
69. .., .., .., .., . .
666 799, . . 1979 (48) 82; Chem. Abstr. 1980 93 71822.
70. .., .., . . . "
", : -, 2001,
. 1, . 128.
, 2

255

71. .., .., .. ., 1992 28 (12) 2545.


72. .., .., .. ., . . .
. . " ", ,
, 1999, . 105.
73. .., .., .. ., . .
.-. . " : ", : . ., 2000, . 42.
74. .., .., .., .., . ,
. . 1997 (7) 1340.
75. .., .., .. ., . . 529 162,
. . 1976 (35) 59; . 1977 22120.
76. .., .., .., 1991 (6) 856.
77. Gardner T.S., Wenis E., Lee J., J. Org. Chem. 1961 26 (5) 1514.
78. .., .., .. ., . . .
. . " XXI : ", -:
, 1999, . 23; . 2001 19 262.
79. .., .., .. ., . . .
. . " ", ,
, 1999, . 106.
80. .., .., .. .,
. . .-. ., . 85-
" :
", : . ., 2001, . 60.
81. .., . . . , : -, 1997.
82. .., .., .., ..,
1982 18 (1) 193.
83. .., .., .., . . 615 071,
. . 1978 (26) 76; Chem. Abstr. 1978 89 129528.
84. .., .., .., ..,
1977 (6) 755.
85. .., .., .. ., .
. .-. . "
: ", : . .,
2000, . 73.
86. .., .., .. ., . .
" XX ", : ,
2000, . 110.
87. .., .., .. ., . .
630 254, . . 1978 (40) 36; . 1979 12162.
88. .., .., .. ., .
. .-. ., . 275- . 80- .
"80
: ", : . ., 1998, . 56.
89. .., .., .., 2002 (3) 399.
90. .., .., .., ..,
. . .-. ., . 275- .
80- . "80
256

InterBioScreen

91.

92.
93.
94.
95.

96.
97.
98.
99.

: ", :
. ., 1998, . 61.
.., .., .., .
. . . "
", : -, 2002,
. 147.
.., .., .. ., . .
. " ", : .
-, 2002, . 26.
.., .., .., .., .
,
: -, 2000, . 113.
.., .., .. ., 2000 36 (9) 1381.
.., .., .. ., .
. .-. . "
: ", : . .,
2000, . 52.
.., .., .. ., . . 677 328,
. . 1981 (1) 242.
.., .., .., .., 1981 17
(5) 1116.
.., 2001 (8) 1011.
Bregant N., Matijevi J., irola I., Balenovi K., Bull. Sci. Cons. Acad. Sci.
et Arts. RSFY 1972 A17 (56) 148; . 1973 4281.

, 2

257


.
2. ,
- 1
..
- . ..
195067, -, ., 47
1.
-2,4,6- ( ) 1 ,
. " " .
, - ,
. 1,3-, 1 ( = ,
R = R' = H) - ,
(5) (4) (6),
(5)-(6)-(6).
O
R'
X

O
R'

N
R
1

X = O, S; R, R' = H, Alk, Ar

N
N
R

, ,
1,
2.
- ,
1 , , .
,
.
1

. . .., .
, . .., .: IBS PRESS, 2003, . 1, . 314.

258

InterBioScreen

2. [2,3-d]-2,4-
5-- 5- . , 5- 3
1,3,6--5,6-[2,3-d]-2,4- 4 [1].
, , , 3. 4
1,3--6- 7 [1], 1,3-
5 1,3--6- 6 [2].

O
N
N

N
N

O
POCl3

N
O

HO

N
N

3a

O
+
H

N
Na

Cl

5,5- 8 (R = CH2CH=CH2, R' = H, Me) HBr


10 [3], 2- 9 [4]. 5-5- 8 5-(2-)-5- [5, 6].

O
R'
O

N
N
H
8

O
HBr
Me2NH

R'
O

N
N
H

R'

10

5-- 11
12 [7, 8].
, 2

259

OH

HN

HN
N
H

O
N
H OH

11

12

R = Alk

5 1,1- 13,
14,
13% [9].

O
Cl

N
N

HO

O
N

13

N
14

1,3--5- 15 (R = H, Alk),
- 15. 5-
16 17 (R = H),
(R = , Alk) 17 [1012].

O
N
O

R
N

O
N

OH
R

15

O
CH2N2

R
N

N
N

15a

OMe

16

17

1,3--2- 18
5- 19
2,3--3- 20 [13].
O

O
Ar
S

Cl

N
N
Ar
18

260

Cl

R3N

O
Ar
S

Cl
O

N
N
Ar
19

OH

O
Ar
S

N
N
Ar

20

InterBioScreen

21
22 [14], - 23
[15].

Ar

N
Ar

O
Ar

Cl

Et3N

Br

O
Ar

N
N
Ar

23

21

22

N
Ar

5--2- 24 ( . H2SO4), 25 [16].

O
O

HN
S

N
H

H2SO4

HN
S

N
H
25

24

5- 1,3--5- 26 (R = H, Me) [2,3-d]2,4- 28 [17].

O
R
O

H2O2

N
N
R
26

R
O

O
OH

N
N
R

POCl3
170C

R
O

N
N
R

27

O
28

Pd, 250C

26 28
(250), , (83%). 5-5- 27, 26, 28 [17].
, 2

261

3. [2,3-d]-2,4-
, ,
,
(5)-(6)-(6) .
O
Ar

Br

N
N
Ar

Br

K2CO3

Ar

21

29

OH

HN
N
H

N
Ar

HCl

HN
O

N
H

31

30
R = H, Alk

1,3- 21 1,3-
2,4- -5- 29 [18]. , ,
- .
31
HCl - 30,
RCH+,
=(6) [19, 20].
5--5-(3-) 32 33 [5, 6].

O
R3N

HN
O

N
H
32

Br

HN
O

N
33


. 1,3- 5
262

InterBioScreen

34 (R = Me) 5- 35,
36
[21, 22].
O
N
O

+
N

O
N
N

34

35

R
O

H
N

36
R = H, Me

5
, 37
[23] 38 [22].
O

H
H
O

O
37

N
5

O
( )n

N
O

H
N

O
38

( )n
n = 14

, 2

263

5 39 ( = CH2) [24, 25], = O [26, 27],


= S [24], = NSO2Me [24].
40 [28] 41 [29].
OH
O

OH
O

MeO2C
H

OH

N
O

O
H

OMe

N
O

5
O
H

O
OH

H
O

HO

41

OH

Ph

OH

O
O H

N
O

H OH
Ph

O
40

39
Ar

NC

Ar
R

HN

X
O

N
H

CN

Ar
R

HN
X

N
H

NH2

43

42

HN
X

N
H

NC

CN

NC

CN

O NC CN

X
R = CN, CO2Et; X = O, S

264

CN

HN
N
H

NH2

44

InterBioScreen

NC

N
R'

HN
N
R

R'
O N
O

CN
O

CN

HN
O

N
R

NH2

45

R = H, Ph; R' = H, Alk


5- 42, 7--5--5-[2,3-d]-2,4-
43 [3033].
44 [34], 45 (R = H [35, 36] R = Ph [37]).
5- 46 1,1-()-2,2-
47, 48 [38].

Ar

N
O

Ar

46

F
F
NMe2
NMe2

N
O

HCl

47

Ar

N
O

OH

POCl3

Ar

N
O

F
F

48

,
90%- 49 1,3--2- 21 , [39].
, 2

265

O
Ar

Ar

N
N
Ar

Et3N

N
N
Ar

21

O
Ar

Ar

N
N
Ar

OH

N
Ar

49

[40] 1,3--2- [41, 42] 50.

O
R

R'

Ar

N
N
R

P2O5 /AcOH

R'

N
R

Ar

50

R = H, Me, Ar; R' = Alk, Ar; X = O, S

2,4- 52 5- 51
( ,
) [43].

O
Ar

HN
O

N
H
51

Ph

Ar

N
H

HN
O

Ph

52

2--3-[2,3-d]-2,4- 54, ,
, , 21
[44], 5- 53,
[4446].
266

InterBioScreen

O
R

+
N
R

OEt
EtO

AcOH

OEt

21

O HN
R

+
N
R

53

O
R'

OEt

N
N
R

Ar

EtONa

54

OEt

R = , , Ar; R' = CN, CO2Et; X = O, S

, 2- 55 , 56 [47].
O

OEt

HN
S

N
H

HN
S

55

O
Ar
S

57

OH

56

CN
CN

N
Ar

N
H

AcONa

O
Ar
S

O
CN

N
N
Ar

NH

HBr

Ar

58

N
Ar

59

5- 57 58,
2- 59 [48].
1 - 3--2--3-[2,3-d]-2,4- 60 [49], 60
1 -5- [50].
, 2

267

MeO
O
O
N

N
H

Ph

HN

NH

HN
N
H

Ph

N
H

OEt

Ph

AcOH

60

N
AcOH

4--5-[2,3-d]-2,4- 61, , 5- 57
25 [18].
O

O
Ar

HCO2Et Ar N

N
Ar

Na

OH

P2O5

N
Ar

OH

Ar

N
Ar

OH

61

57

, 5- 62 63, 64 [51].
O
N
H

O
Ar
S

BF3, ClSO2Me

O
Ar

N
Ar

62

OH
Ac2O
AcONa

Ar
S

Ph

Ph

N
Ar

63

O
Ph

N
N
Ar

O
64

1,3--5- - 65, 96%


2,3--4- 66 [52].
268

InterBioScreen

O
N
N

OH

H2SO4

Ar
R2NH

OH

N
O

Ar

66

65

Ar = p-ClC6H4

Ar

66 () [53].
1,3- , 2- , 67 [54].
2- 1,3- [54].
R"

O
R

R'
O

N
N
R

R"'

Cl
+
H

R"'
R"

O
N
R 67

R'

R = , Ar; R' = Alk; R'', R''' = H, Alk; X = O, S

X
O

HO

Ac2O

HN

HN
N
H

OH

N
H

HN
HO
O

NH
O

O
72

N
H

[H]

NH
O

HN
N
H

69

HN
O

HN

X
N

OH

HN
HO
O

HN
O

68

O
HN

N
H

O
70

X
N
H

, 2

O
71

269


-,
5--10- 69 (X = H).
69
5-, - [55],
, , . [5558]. 5--10- 69
1 , 5--
68 [59].
69 -5--10-
71 [55]. , 5--10- 69
1, 70,
68 1 [60].
1 2--1- 5- 72 [61].
5- , 5-[2,3-d:6,5-d] 75, 73 .
( .) 2-
, 46, -5,5- 73,
74 [62, 63].

O
R
2

Py

N
N
R

O
N

O
N
OH
R

Ar

R = , Ar; X = O, S

73

N
R

Ar

R POCl R
3
N
X

PyH

N
N
R

N
R

R
X

74

[2,3-d]
76, 1,3- 5 2-3-, , 75 5 [64].

O
N
O

H
N

O
N

+
5

270

N
H

R2NH

O O
75

InterBioScreen

O
N

N
N

O
76

78
77 78 [65].

O
O

HN
O

O
O

HN

+
N
H

O
N
H

HN
N
H

77

OH

78

4.

, , .
, 1,3--6-(2-) 79
2--1,4- 80 [66].

O
POCl3

N
O

NH2
R

R'

HNO2

R'

N
N

N
H

N
O

79

O
R'
R

80

R, R' = Alk

5 81 [67].
, 2

271

O
HO

N
O

OH
K3[Fe(CN)6]

+
N

OH

N
O

N
O

OH

O
N

N
81

,
, .
5-(N-)-1,3- 82 -[4,5-b][1,4,6]- 83, [68].
R

R
OEt
N
N

O
N

N
O

OH

NH

OEt

O
O

OEt

Ar

OH

N
NH HN

N
Ar

O
O
OEt

82

Ar

O
N

N
O

NH

O
R
83

R= H, Alk, OAlk


(5). , [4,5-b]- , ,
,
N(1), [1,2-b]- [4,3-d]-. , N(1)-(2)(O)-N(3) 1, ,
-
272

InterBioScreen

(4)-(4)-(5)-(6)-(6), N(1)
1, , , - .
, 5- 84 1,3- [4,3-d] 85,
[1,2-b] 86 [69, 70].

O
X

HN

HO , C6H6

85

HN
O

N
H

OH
X

84

HO , C6H6 /H2O

O
86

X = Cl, Br

, , 84,
.
1--5- 87 HBr
1-(2-)-5- ,
[4,3-d] 88 [69].

O
Ph

HN
O

87

HBr

O
Ph

HN
O

HO

Ph

HN
O

Br

88

1---3,5,5-
89
90 [71].
, 2

273

O
Ph

O
H2/PdO2

N
N

O
O

Ph

O
OH

N
N

O
90

89

91 1--5- 92
[3',4'-a]-[4'',5''-d] 93 [72].

O
Ph
O

H
Ph

+
O

N+

Ph

N
N
H

N
O

92

91

Ph
O

93

,
1,4-, , in situ
91, 92.
1-[2-([1,3]-5-)1--]- 94 ,
[][1,6-]
95 [73].

Cl
POCl3

HN
O

O
O
94

N
O

O
O

O
N

O
O
95

5.
[2,3-d]- [2,3-d]-2,4- 6- . , [2,3-d] 97 , 2--5- 6- 96, [16].
274

InterBioScreen

O
POCl3

HN
N
H

H2N

O
H2SO4

HN

N
H

NH2

HN
S

N
H
97

96

[2,3-d] 98 1,3- 5, 5--6-, [74].

POCl3

N
O

OEt

SH

N
O

Cl

OEt

98

98 1,3-6- [74].
5--6- 99
100 [75, 76].

X
NH2

HN
X

N
H

HCO2H

SH

HN
X

99

N
H
100

X = O, S, NH

102, , 5-
101 N- [77], .
S

O
Br

HN
O

N
H
101

H2N

N
H

HN
N
H

N
H

102

, 2

275

101 4-

N-[5,4-d] 103,
103
1,3,4-[5,6-d] 104 [78].

O
Et3N

O
Br

HN
O

+
N
H

H2N

N
H

N
H
103

NH
R

N
NH2
R
NH

O
Py

101

HN

HN
O

N
H

N
H

104

1,3--5--6- 105
106 [79].

O
NH2

N
O

O
N

Br

SH

+
H

105

106

3--2,3-[5,4-d] 109 . 1,3-


5 N- 107, 6
, 1,3--5--6-
108 109 [80].

O
5

Br

POCl3/

NBS

N
107

276

Cl

RNH2
NaHS

N
H
SH

N
O

108

InterBioScreen

O
I2

Et3N

N R

N
109
R = Alk

110
2--1,3-[4,5-d] 111,
[81]. 2- 112 [81].

O
S

HN
O

Et
N

N
H

O
Et H2SO4

O
S

HN
O

N
H

110

Et
N+
Et

HN
O

Se
S

N
H
112

111

- 113

. , 5- 98 114,
115 [82].

SH

Br

HN

+
N
H
98

113

HN
O

NH2

NH2

N
H

OH

HCl
EtOH

O
S

HN
O

N
H

114

N
H
115

117

116 - [83]. 117 5 113 [84].
, 2

277

N
R

N
R

SH

S+

R
Me2SO
N

NH2

116

HS

+
N

(PhCO)2O2

X
N
R

NH2

N
H
117

113

R = H, Me; X = H, Cl

1,4-[2,3-d:6,5-d] 120
1,3--5- 118 5--6- 119 [82].
1,3--5--6- 121 122,
120 [85].

O
Cl

+
N

OH

119

O
POCl3

N
5

HNO3

HS

118

N
O

H2N

O
NO2

N
N

119

N
H
120

N
N
R

Cl

121
R = OMe, AlkNH, Alk2N

-5- 122, 5 , 1,4-[2,3-d:6,5-d] 123 [86].


278

InterBioScreen

O
S2Cl2

N
N

N
O

HO
OH

POCl3

N
N

O
S

N
O

122

123

5--6- 124, 1- , 4--2-5- 125, -


126 [87].
O
R

H
N
H

Ph

NH2

POCl3

124

NH

Cl

125

Ph

126

R = Alk, Ar

[1,2-b] [1,2-b] 2- ,
, ,
.
2- ,
N(1) (2),
.
30 1,2- 1,3-
, ,
127 128 [88].

O
N
S

Hal

N
127

OH

Hal
NaOH

HN
S

N
H

Hal

Hal
NaOH

30

OH

128

127, 128 -
130 [88, 89].
,
, 5- , 2

279

129, , 130
131.

OH
X

n( ) N

X
O

n( ) N

OH

127 n = 2;
128 n = 3

129

X
O

n( ) N

OH

X
N

OH

n( ) N

130

OH

131

30 132,
3-[3,2-]7-3,4--1--5- 133 [90].
133 ,
134 [90].
O

HN

Br

HN
S

Ph

N
H

NaOH

30

Ph
H2SO4

132

MeOH

N
133

OH

Ph

N
S

OH

N
S

N
O H

134

, 135, , 280

InterBioScreen

3,7--6,7--5-8--1-3,9--[b]-4- 136 [91].


Ph

Ph
O

O
HN
S

Ph
Br

N
H

H2SO4

HN

NaOH

Ph

OH

N
S

Ph

O
Ph

135

136

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.

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282

InterBioScreen

65. Ahluwalia V.K., Kumar R., Aggarwal R., Org. Prep. Proced. Int. 1992 24 (6) 675.
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73. Kienzle F., Bounameaux Y., Minder R.E., Muggli R., Helv. Chim. Acta 1986
69 1671.
74. Hirota K., Shirahashi M., Senda S., Yogo M., J. Heterocycl. Chem. 1990 27 717.
75. Hahn H., Prijs B., Erlenmeyer H., Helv. Chim. Acta 1956 39 (2) 341.
76. Elion G.B., Lange W.H., Hitchings G.H., J. Am. Chem. Soc. 1956 78 2858.
77. Nightingall D., Morris L.C., J. Am. Chem. Soc. 1936 58 1469.
78. hande S.M., Joshi R.D., Indian J. Chem., Sect. B 1996 35 251.
79. Fenner H., Motschall H., Tetrahedron Lett. 1971 4185.
80. Decicco C.P., Nelson D.J., Tetrahedron Lett. 1993 34 (51) 8213.
81. .., .., .., 1992 1667.
82. Fenner H., Grauert R.W., Hemerich P., Liebigs Ann. Chem. 1978 2 193.
83. Fenner H., Rossler H.H., Grauert R.W., Arch. Pharm. (Weinheim) 1981 314 1015.
84. Ahluwalia V.K., Aggarwal R., Kumar R., Indian J. Chem., Sect. B 1994 33 65.
85. .., .., .. ., 1989 2 258.
86. Gompper R., Euchner H., Kast H., Liebigs Ann. Chem. 1964 675 151.
87. .., .., 1984 (8) 1126.
88. .., .., N PCT/RU97/00098, 1997;
WO 98/43 982, 1998.
89. .., .., 2 169 732, . . 2001
(18) 46.
90. .., . - ,
. .., .: IBS PRESS, 2003.
91. .., . - ,
. .., .: IBS PRESS, 2003.

, 2

283


.., .., ..
. ..
664033, , . , 1

, , .
. 40 [1, 2]
, , , , , , .
2-, 2-()
2,2-.
,
, 2,2-
-, - -, ,
() (
CH3C(O)CH=C=S) . -1,2-- 2,2-
20002001 .
O-, N-, N,N-,
N,O-, N,S-, S,S- . 1--, 2-, 1,2-, 2,2- 2,2-, 19672001 .
1. 2,2-
. , (2,2-), ,
AlCl3, Mg(ClO4)2
6-(2,2-)-2 1 [3] ( 1).
,
1 [4]. 1--2--5-()--6 - - 2,2-(2-) [5] ( 2).

284

InterBioScreen

1
R'
R

Cl
Cl

Cl

R
Cl

R'
CCl2

H2O

Cl

R'

Cl

Cl

CCl2

Cl

R
R'

H2O

Cl

Cl

1
R = Me, Et; R' = H, Me

Cl

Cl
X

X
OEt

Cl
O

Cl

Cl
Cl

Cl
O

Cl
Z

Cl
Cl

Cl
Cl

OEt

Cl

Cl
1

X = H, Cl; Y = H, Cl; Z = H, CO2Et


. 1 , , , ,
[35].
, 2

285

2. 2- , ,
, , 97%
- -2,2- 2 [6]
( 3).
3
R

Cl
O

R'

Cl

H
N

R'
N

R
R''

R"

Cl
2

R = Me, Ph, 4-MeC6H4, 4-BrC6H4, 4-NO2C6H4;


N

NR'R" =

; N

O ; N

2,2-, N- 2,2-(-1-) 3 [7] ( 4).


4

Cl
O

SiMe3
N

Cl

N
R

N
O

2 Me3SiCl

N
N
3

R = Me, Ph, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, 4-ClC6H4, 2,4,6-MeC6H2,


O
S
,
N
O

2
( 5). , , - 1-(2--1) N-() 4 - 4b, N-[()] 5 N-[2-1-()] 6a, b, . 6a
-2,2- [6].
286

InterBioScreen

5
O

H2O

4a Het =

Het

; 4b Het = N

O
2

H2S

N
S
O

RSNa

6a R = Me; 6b R = Ph

N
S R

2
( 6).
6

R'NH2

N
H

R'

, t

7a, b

PhNHNH2

Ph

N N

Ph

Ph
NaN3
H2O

Het
R'
O

N
N N
H

9ae

7a R' = H; 7b R' = Ph;


9 R' = Ph (a, d, e), 4-MeC6H4 (b), 4-BrC6H4 (c);
N
(ac), N
Het =
(e)
O (d), N

, 2

287

,
7b . ,
N-(-3-) 8.
4-()()-5- 9a [6].
- 2
10a, b. 10b ,
- 11 [6] ( 7).
7
O

Cl

t-BuOK

Het HCl

Ph

O
Het

SH

Ph

Ph

10a, b

N
O

Het =

N
(10a), N

11

O (10b)

[8] 2-, ( 8).


8
H
N

O
R

K2CO3, TEBA

Cl

R'
N
R

R'
N

R = Me, Et, Pr; R' = trans-CH=CHC(O)Me, H

3.
[2] , -2,2- 2-,
N,O-, N,N-, N,S--
.
288

InterBioScreen

, , -,
-2,2-- 1,2,2- , 12, 13
[913] ( 9).
9
NH2

H
N

YH

Y
O

R
O

12

Cl
Cl
X
HY

H
N

NH2

Y
13

R
O

12 R = CH2Cl, CF3, Ph; X = H; Y = NH, O;


R = CH2Cl; X = Cl; Y = NH, O;
13 R = CH2Cl; X = Cl; Y = NH, O

,
. , -2,2- - , ( 10).
10

O
Alk

Cl
Cl

H
N

NH2
Alk
NH2

N
H
NH2

, 2

289

H
N
Alk

HN

N
H

H
N
Alk
N

H
N
N

Alk = Me, Pr

2-[2--2-(-)] 10.
2,2-
- 2- 2- [12].
1,2- 2,2-, ()-2,2-- 1,2,2-
-, 12
[913] (c 9).
1,2,2--1- 1,2- 2--1,3- 14
( 11). ,
, [13].
-2,2- 1--4,4--2 [14], , [14, 15] ( 11). ,
,
, [2].
-,
2,2- [1215] ( 11). ()-2,2 15 [2, 11, 14, 15] ( 11). 3,3--2- 2SO4
2--3- 16. SOCl2
2,3- [13] ( 11).
-, -2,2- ()
. , 17 [6] ( 12).
290

InterBioScreen

11
Ph

H
N

N
H

Ph Cl
N

Ph

Cl
14

R = H, R1 = Cl

N
Ph
R
R

Cl

3
4

R
O

Cl

ArNH2

Cl

HN

R1 = H R

NH

NH
Ar

R2

15

R
4

PhNH2
R = H, R1 = Cl

HN

NH

Cl

H2SO4

OH

16
R = Me, i-Pr, CH2Cl, Ph; R2 = H, Me; R3 = H, Cl; R4 = H, Br, Me;
Ar = Ph, 3-MeC6H4, 3-BrC6H4, 2-MeC6H4, 4-ClC6H4

12
R'
O
R

S
N
R"

R'

R"
N

i-PrONa

HN
R"'

i-PrOH

N
R"'

17
R = Me, Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4;
R' = Et, Pr, (EtO)2CHCH2, Ph, Bn; R" = H;
R'+R" = (CH2)2O(CH2)2; R'" = H, Me

, 2

291


[16].

HN

Ph

Ph

HN
S

S
O

O
4. 1,3- 2,2-

2,2- , , - , () . , S-
18 19 [1720] ( 13),
[18, 19].
13
O

Cl
Cl

SX

MSX

SX

R
O

Cl

R
S

Cl

R
O

R
O

Cl

Cl

18

S
S

Cl
R

R
O

R
19

M = Na, K; X = Na, C(S)SNa, C(S)OEt, C(S)OBu, C(S)NHEt,


C(S)NHMe, C(S)NEt2, C(S)NMe2, C(O)Me, PhC(O)CH2C(S);
R = H, Me, Et, Pr, i-Pr, Bu, i-Bu, Ht, Ph, 4-MeC6H4, 4-ClC6H4, 2-

292

InterBioScreen

, [19].
[21].

18, 19
13 [19].
,
19 18 -, S-, N-. , 18

- [20].
- 1,3- 2-4,5- 3,4,5,6- [20].
19 :
, , ,
, HgO, AgNO3, Cu ,
HgCl2, . [19].
19
.
R = Me, Pr 1019 / [19].
5. 1,3-
, 2,2-()
, 20 [11, 2225] ( 14).
: ,
1 : 2. , , 20
.
14

Cl

Cl
R'

H2N

R"

R" + NH2
S
O
+ R"
S
R
R'
NH2 2HCl

, 2

293

S
R'
R

S
N

R"

20
R' = H R = Me, CF3, Ph, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, 2-, 2-;
R'' = Me, Et, Ph, NH2, NHMe, NHPh, NHCH2CH=CH2, NMe2, NEt2,
NHC(O)Me, SCH2C6H4, CO2Et;
R' = Cl R = Ph; R" = NH2

, -,
2,2-(), NH2 ,
20 [22, 23].
1 (1,2,2-) [22].
-
. , (2,2-) N-
Cl .
21 [26] (c 15).
15
Cl

Cl

Cl

H 2N

Cl

Cl

H
N

NH
R

21

R = H, Ac

-2,2-

[24, 25]. 16 22 2,2-() [25]. 22
2--2- [24].
16
O
R

Cl

R'SNa

Cl

R'

S
H2N

S
R'

R"

HClO4

R'
S

ClO4
R"

22

R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4;


R' = Me; R" = NH2, Ph

294

InterBioScreen

-6- 20 -
- [22] ( 17).
17
S
YR"
R' = H

S
R

Ac2Hg

S
N

N
R'

R"

S
AlkX

NH
R'

S Cl
R

NH
R'

Alk
S

(COCl)2

S
R

NH
R'

Cl

X
NH
R'

R = Me, Ph; AlkX = MeI, Me2SO4, Et3OBF4; YR" = Ac2O, Me2NCHOMeC(OMe)3, PhNCO;
NR'R" = NHAc, N=CHNMe2, NHC(O)NHPh

( ), () [27]
2-- 2--3-()-6-.
, ()
- - ,
N- .
1 - .
S- ,
,
, , - [23].
6. ()
() . , 2

295

, 1,3-

, .

,
, [28].
2- , 1-, 1--, 1--3-() [1, 2] 60- . XX .
5(4)-() ()
.
[13] . , 3 1,2-, 2,2--, 1,2,2- ,
1- 23 15 78% ( 18).
,
4 4% 1--4,5-.
-1,2,2- 18% 1--4,5--3- 24
( 18).
18

N
R"

O
R

Cl
R'

R"

MeOH
R = CCl3
R' = R" = H

R'

NH2NHPh

Ph
N

Ph
N

O
OMe

AcOH
Et2O
R = H,
R' = R" = Cl

25

Ph
N

R"
R'

HO
24

R = H, CHCl2, CCl=CCl2, Ph; R' = R" = Cl;


R = CHCl2; R' = Cl, R" = H;
R = Me; R' = H, R" = Cl;
R = CCl3, R' = R" = H

. , , 2-() ,
,
1--3- c 25 (X = H).
296

InterBioScreen

[2931], 2,4-
2,2- 5--1-()
2,2-.
--
[29, 30]. [31].

.
[32], (2,2-)
1--5-,
19.
19
O

Cl
Cl

NH2NH2

N
N
Cl

N N
H

H
N

Cl

2HCl

() .
,
, 5-
Pl3 -5- [33, 34]
5- .
(2,2-) -
- ,
.
, (2,2-)
,
, 26 [32] ( 20).
20

O
Ar

Cl
Cl

H2N

N
H

Cl

Ar

O
NH2

Cl
NH

H2N

, 2

297

NH2

H2N

Cl

N
H

H2N
NH2

O
H
N

Ar

Ar

O
N
H

NH2

26

Ar = Ph, 4-MeC6H4, 4-MeOC6H4, 4-NO2C6H4, 3-NO2C6H4

C ,
[32], .
( ), -, (2,2-) 2,2-() 3- 1--5- 27 ( 21).
1 : 1 .
21

Hal
Hal

NH2NHAlk

Et3N

Et3NHHal

Alk
N
Cl
N
R
27

R = Me, Pr, i-Pr, CH2Cl, CF3, Ph, 4-NO2C6H4;


Hal = Cl, Br; Alk = Me, Et, Ht

, -,
2,2-
-
. N-
.
, 1--4- 28 ( 22) 1,2- (
).
22
O

Cl

Cl

NH2NHAlk

Cl

Et3NHCl

Alk
N

R = Me, Et, Pr; Alk = Et, Ht

298

Et3N

Cl
28

InterBioScreen

2-- 2,2-() , 3-
1--, 1--5-- 1--5- 29 [3538]
( 23). 90% 1,1,1-.
23

O
R

Hal
X

NH2NMe2

NH2NMe2
MeHal

N
R

Hal
X

N
R

N+

Hal

NH2NMe3Hal

29

R = Me, Et, Pr, i-Pr, CH2Cl, CF3, Ph, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4,
4-ClC6H4, 4-NO2C6H4, 3-NO2C6H4; Hal = Cl, Br; X = H, Cl, Br

1- 29 .
, -,

N - -
N,N- -,
1,1-
29.
, 1-[1-()(H)-2-]-1,1- .
1-[1--2-(2-)]-1,1- 1,1-, .
[39].
, 1--3--, -,
-, -5-
, ,
, 1,1- , 2

299


[40].
4- 5-() 2729
,
[41],
, .
4- 5-() ,
[42],
[41, 4347]. , , 1,3--5-
[41, 43]. 3--1-5- ,
[45, 46],
4-, [47].
1--5(4)-() ,
[44, 45, 48].
7. ,
7.1 2,2-
2,2- ,
50% 5- 3- 30 [49],
( 24).
, -
, (
1.5 1 )
: = = .
24

Cl

NaN3

Cl NaCl

Cl

O
N3

O
Cl

R
R = Pr, Ph

300

Cl

NaN3
NaCl
N2

NaN3
NaCl
N2

N2

Cl
N

N3

R
30

InterBioScreen

7.2
[50] (2-) 0,
2-,
5--2- 31 ( 25).
25

Ph

O
O

NH4OH

Ph

Cl

H2O
HCl

Ph

Ph

Cl
H2O
HCl

NH2

N
Ph
31

7.3 (2--1,2-)

(1--2-) [51] ( 26).
(1-) (2--1,2-) . (1-)
[52].
() 1--2- ,
. ( 26). ,
(,-)
- 2--1- 32. RF = CF3
: 33. -, , ( RF = CHF2
), CF3, , .
26
NH2

Br

RF
Br

Et3N

NH2

MeOH

RF
Br

, 2

301

RF
N
R
Br

RF

32

NH
NH2

O
RF = CF3

Ph

Ph

CF3

CF3
33
RF = CF3, CHF2, CF2CF2H, C4F9, C6F13; R = Ph, 4-ClC6H4

(1,2-) , , - 3,3'--4,4'- 34
[51] ( 27). (1,2-), ,
, ,
1,4-[4,1,0]-4- 35 [53] ( 27).
27

Ar
N

R = Ar;
X = (CH2)2

Br

Ph

H2N

NH2

Et3N

Ph

N
35

MeOH

RF

Br

H
N

H
N

RF

R = RF

Ph

34

RF = CF3, CF2CF2H, C3F7, C8F17;


Ar = Ph, 3-NO2C6H4, 4-NO2C6H4;
X = (CH2)2, (CH2)6,

,
Me

302

Ph

Me

InterBioScreen


19672001 .
(1-), (1,2-)-, (2,2-) 2,2-().
,
[9, 10, 5052, 54, 55].

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.

.., 1955 24 32.


Pohland A.E., Benson W.R., Chem. Rev. 1966 (2) 161.
.., .., .., . , . .
1977 (7) 1816.
Pochat F., Levas E., Bull. Soc. Chim. Fr. 1972 (8) 3145.
Pochat F., Levas E., Bull. Soc. Chim. Fr. 1972 (8) 3151.
Schroth W., Spitzner R., Hugo S., Synthesis 1982 (3) 199.
Hoffmann S., Hildebrandt A., Hartung K.-J., et al., Z. Chem. 1974 14 (5) 188.
Jian Zhou, Lande Zhang, Hongwen Hu, SO Huaxue Tongbao 1998 (10) 33;
Chem. Abstr. 1999 130 81457.
.., .., O 1994 30 (2) 187.
.., .., .., O 1982 18 (9) 1835.
.., .., .. ., 2001 37 (5) 684.
.., .., .., .., 1984
20 (3) 634.
Roedig A., Becker H.-J., Liebigs Ann. Chem. 1955 597 (3) 214.
.., .., .., .., 1974 10
(3) 2293.
Soulen R.L., Kundiger D.G., Searles S., Sanches J.R., J. Org. Chem. 1967 32 (9)
2661.
Aggarwal V., Singh G., Ila H., Junjappa H., Synthesis 1982 214.
Schroth W., Schmiedl D., Hildebrandt A., Z. Chem. 1974 14 (3) 92.
.., .., .., 1976 12 (5) 1123.
.., .., .. ., . ,
. . 1976 (9) 2040.
Schroth W., Uhlig H.-F., Bahn H., et al., Z. Chem. 1974 14 (5) 186.
Shafiee A., Lalezeri I., J. Heterocycl. Chem. 1973 10 (1) 11.
Schroth W., Dill G., Dung N., et al., Z. Chem. 1974 14 (2) 52.
.., .., .., 1976 12 (4) 904.
Schroth W., Spitzner R., Koch B., Synthesis 1982 203.
Spitzner R., Menzel M., Schroth W., Synthesis 1982 206.
.., .., .., .., 1979
15 (11) 2301.
.., .., .., O 2002 38 (1) 140.
Makino K., Kim H.S., Kurasawa Y., J. Heterocycl. Chem. 1998 35 489.
.., .., .. ., . ,
. . 1973 (10) 2235.

, 2

303

30. .., .., .. ., . ,


. . 1974 (6) 1402.
31. .., .., .., .., .-.
. 1977 (3) 74.
32. .., .., .., . , . .
1981 (6) 1349
33. Bjrkqvist B., Helgstrand E., Stjernstrm N.E., Acta Chem. Scand. 1967 21 (8) 2295.
34. .., .., .., 1996 (7) 927.
35. .., .., .., ..,
2001 37 (12) 1876.
36. .., .., .., .., . 1 .
. .. , , 2000, c. 257.
37. .., .., .., ..,
99 123 778/04; . . 2001 25 (1) 82.
38. .., .., .., .
, . .., .., .:
-, 2001, . 2, . 184.
39. .., .., .. ., . , . . 1999
(8) 1536.
40. .., N,N- , :
, 1999.
41. .., 1999 68 (8) 773.
42. Suzuki F., Iwakawa I., et al., Jp. Kokai. Tokyo Koho Jpn. 06 56 792 [94 56,792];
hem. Abstr. 1995 122 31573f.
43. Pawer A., Patil A.A., Indian J. Chem., Sect. B 1994 33 156.
44. Butler D.E., De Ward H.A., J. Org. Chem. 1971 36 2542.
45. Fray M.J., Bull D., Cooper K., et al., J. Med. Chem. 1995 38 3524.
46. Nazarinia M., Sharifian A., Shafiee A., J. Heterocycl. Chem. 1995 32 (2) 223.
47. ., ., .-. ., 2 072 991; . . 1997
(4); . 1998 19370.
48. Michaelis ., Dorn ., Ber. 1907 23 179; Liebigs Ann. Chem. 1907 352 169;
Auwers ., Hollmann ., Ber. 1926 59 (4) 601; Butler D.E., De Ward H.A.,
J. Org. Chem. 1971 36 2542; Auwers K., Niemyer F., J. Prakt. Chem. 1925 110
153; Habraken C.L., Moore J.A., J. Org. Chem. 1965 30 1892.
49. .., .., 1986 22 (4) 889.
50. Onural Yucel, Chim. Acta Tere. 1990 18 (1) 125; . 1992 6168.
51. .., .., 1999 35 (1) 106.
52. .., .., .., . , . . 1993 (12) 2134.
53. Heine H.W., Henzel R.P., J. Org. Chem. 1969 34 (10) 171.
54. (a) Cheon S.H., Christ W.J., Hawkins L.O., et al., Tetrahedron Lett. 1986 27 (39)
4759; (b) Taniguchi M., Kobayashi S., Nakagawa M., Hino T., Tetrahedron Lett.
1986 27 (39) 4763; (c)Taniguchi M., Kishi Y., Tetrahedron Lett. 1986 27 (39) 4767.
55. (a) Manoiu M., Dinulescu I.G., Avram M., Rev. Roum. Chim. 1985 30 (3) 223;
(b) .., .., .., O 1993 29 (5) 1069;
(c) Bhalerao U.T., Sridhar D., Dasardhi L., Rao BV., Synth. Commun. 1993 23 (16)
2213; (d) Conde J.J., Nartucci V., Olsen M., Tetrahedron Lett. 2000 (41) 4709;
(e) Reddy D.B., Babu N.C., Indian J. Chem. 1999 37 (3) 275; (f) Wilson B.D.,
Synthesis 1992 (3) 283.
304

InterBioScreen

1,4-
..1, ..2, ..1
1


02094, , . , 5
2
. ..
14038, , . , 53
, 1,4-, -1,4-
. [1] 1982 .
.
1,4-, 1015 .
1,4-
1,4-
[1] , 2- 1 1,2- 2- [2].
[3] 2-3,4--1,4- 2,
80.8%
1 1,2-
4 Na2CO3 0.5 ( 1).
1
SH
NH2
1

ClCH2CH2Cl
Na2CO3, NaI
2

N
H

2--4- 1,4- 2,5-


,
Na2S [4].

1,4- 2-
- - [530]. ,
3
, 2

305

. 2--1,4- 3 (R = 2-, 2-, 2-, 3-, 4-) -


[31]. 3 (R2 = Cl, R3 = R5 = H, R4 = F) 30%-
[24] 4 ( 2).
2
R2

NH2 R

SH
R

O
R'

R
4

R2

H
N

H 2O 2

R AcOH

H
N

R O O

2-() 5 4-2- 6
[32] 7 8 - - .
5 4--2- 9
10 11
( 3).
3
Cl

1:1

Br

9
K2CO3

OMe

O
OMe

N
7

NH

OMe

K2CO3

SH

O
S

OMe

OMe

+
N

N
O
10

OMe
9:1

11

2-
[33] 3,4--3-2-1,4--2- 12 7594% ( 4).
306

InterBioScreen

4
R
R'

NH2

R"

SH

R'

H
N

R"

SH

O
O

R
R'

H
N

R"

S
12

OH

OH

R, R', R" = H, Cl, Br, Me, OMe

1,6--3,4--2,4--1,6- 13 - 3--2,3--4-1,4--2- 14 [34]. 14


- . - 3,4--2--6--6--2,4- 15
14 2--2,3--4-1,4-3- 16 ( 5).
5

O
OH O
Ph

Ph
O

H
N

NH2

SH

OH

Ph

PhCOMe
H2O

13

14

Ph
O
OH

HO

H
N

NH2
SH

H2NCOCH2CO2Et
H2O

NH2 OEt
15

, 2

S
Ph

16

307

17 - [35, 36]
1,4- 18 ( 6).
6
O
R

MeO

SH

OH
Br

MeO

NH2

R'

R'
17

N
H

18
R = H, Me, Et, Bu, Ph

19, 2- 2--2-(2-) ,
20
21 [3749] ( 7).
7

SH

+
NH2

O
MeO
Br

N
H

OMe

OMe

19

O
O
MeI
BBr3

S
N
20

S
O

OH

R
O

O
( )n ( )m

21

(2-) 22 [50] 6-R-2-N,N--3--1,4- 23 ( 8).


308

InterBioScreen

8
O
S

POCl3

NH2

OH

22

Cl

23
R = H, Cl

(2-) 24
7386%
25, - 26 ( = S) 26 (X = NPh). 26 [51] 2--3-- N--2--3--2,3--1,4- 27
( 9).
9

Ar
S
NH2

Ar

Ar
PhNCO

S CS
2

S NaH

Ar

N
PPh3

NCX

N
H

Ph3PBr2
Et3N

25

24

X = S, NPh

27

26

[52] N--N--2-() 28
50 87% 4--2,3--4-1,4- 29
( 10).
10

S
N
Et
28

Ph
COPh

(Me2CH)2NLi
T

Ph

N
Et

Ph

29

(2-) 30, 2- , 31 (n = 1) 31 (n = 2).


, 2

309

[53] 32 ( 11).
11
CN

( O)n
S

H2O2

NH2

CN

5% HClEtOH

NH2

OEt

NH2

32

31

30

( O)n
S

2- 33 [54] 2--2--2-1,4--3(4)- 34 ( 12).


12

CF3 O
HO

NH2
SH

OH
F3C
OH
O

OH

S
H2O

H2O

NH2

OH
33

OH
CF3

N
H

34

24
2- 3--5(4)- 35
6888% [55] 3,3'--2,2'--(2-1,4-) 36 ( 13).
13

NH2
SH

Ar

N
CO2
O

NH3

Ar
H2

35

S
36

310

Ar

Ar

InterBioScreen

N,N- 37
25 50 70% [56] 2,2-4--2-1,4--3(4)- 38. 2,2- 39 ( 14).
14

SOCl2

R
37

R = H, Me

Cl
Cl

OMe
OMe

MeOH

38

39

40
SOCl2 20 7-R-2--2--2-1,4--3(4)- 41, Cl
[5759]
42. 42 (Nu = NCS)
43.
7R-(2'--3,5'-(2,3--1,4--2,4'-) 44, c [60]
( 15).
15
OEt
R

O SOCl2
N
H

42

CO2Et
R
Cl HNu

S
N
H

40

ArNH2

N
H

N
H

Nu = NCS
43

H
N Ar
NH
CO2Et
O

42

41
R = Cl, Me; Nu = OH, OEt, NR'R", N3

S
S

CO2Et
Nu

O
S

EtOH

N
H

Ar
N

N
H
O

44

, 2

311

45 [61] 4-1,4- 46
( 16).
16

R
O

S
NH2

OEt

H2N

45

46

R = H, Alk, OAlk

OEt

N
H


SS (-) 47
- [62]
3-R-6-X-2H- 48 4086%.
, ( 17).
17
X
NO2 S
S
X

NO2

SmI2
RCOCH2Br

S
48

47

4-(4-)3--4- 49 4--7-(4--6--1,2,5,6-3-)-3,4--2-1,4--3- 50,


[63] ( 18).
18

H2N

312

OMe
KSCN, Br2,
AcOH
Na2S, H2O

49

OMe

HS
H2N

InterBioScreen

Cl

Cl
K2CO3

OMe

O
S

MeI, NaH
NH2NH2

N
H

NH

N
50

3,4--2-1,4--7- 51
4--3- ( , 4- 2--6- )
[64]. 51 N-[4-(2,4--6-)-3,4--2-1,4--7-]-L- 52 (-68)
( 19).
19
NH2

NHTs

NH2
SH

Cl

Br

NaOH

Cl

CO2H

TsCl
Py

Cl
CO2H

CO2H
Ts
N

NaH

H
N

NaOH
HBr

OMe

H2N

N
N

S
OMe

51

CO2H

H
N

NH2
MX-68
52

CO2H


3--2-(2,5-)-2- 53 [65]
N- 2--4-1,4--1,1- 54 ( 20).
, 2

313

20
O O
S

Cl

Cl

CO2Et

O O
S

Cl

K2CO3/MeCN
18--6

NH

CO2Et

53

54

2--4,5- 55 - .
,
3--6,7--4-1,4--1,1- 56.
57,
2--6,7--1,4-4--1,1- 58.

6 59 60 [66, 67] ( 21).
21
O

SO2Na

60

MeO

Br

Br

O
S
O

HC(OEt)3 F

NH2
57

N
H

Ph

N
H

56

55

O O
S

Br

NH2

O O
S

R = Ph, OMe

O O
S
N
H

F
58

O
F

O O
S

N
N

O
R

N
H
59

61 89%
2,3,4,5- 62. 3-() 63
64 (n = 0) - -. 314

InterBioScreen

- 51%.
-
64 (n = 1) ( 1.3 ),
64 (n = 2) ( 3.1 ).
,
65. 6-
N- [68] 66 67. , 4
67 ( 66) ( 22).
22

SH

Cl
S

OEt

+
F

61

62

NH

OEt

NH

F
64

63

( O )n O
S

(O)n O
S

OEt

( O)n
S

OH

65

66

O
F

OH
N

N
N

F
67

, 5--2,4- 68
69. N,N-
, 2

315

58% [69] 3--2-(2-5--4-) 70.



7--6--4-1,4--2- 71,
N- 72 ( 23).
23

68

SH

NO2

Cl

OMe
Et3N

69

MeO

OEt

OEt

S
NO2

Cl

NO2

Cl

70

O
H2/Ni- F

O
OMe

EtI
K2CO3

N
H

Cl

OMe

OMe

N
Et

Cl

71

72

4-(4-)2,3,5- 73 N,N-, 2- 61%


10-(4-)-7--9-2,3--7-[1,4][2,3,4-ij]-6- 74 "" [70] ( 24).
24

O
MeO

N
N

316

OEt

OEt

OMe

F
F

73

InterBioScreen

NH2

O
F

SH

+
H

OMe
N

OH

N
74

74 [71, 72]
- 75 ,
1,4- 76 77 ( 25).
25
O
OH

Cl

SH

FeSO4

NO2

NO2

Cl

Cl

LiAlH4

Cl
75

O
OEt

NH

Y
S
76

OH

OEt O

Cl

NH

Cl

OEt

OEt

Y
S
77

[73].
- 78 20 6483% 2--4--6R- 79,
80.
81
2040 3--2,3--1,4--1,1- 82 ( 26).
, 2

317

26

O
O

NH2

NO2

HN

SBn PhI(OAc) R
2

BnSH

OMe
SBn

MeOH

K2CO3

NO2

NH2

78

NO2

NO2

79

80

H2O2

OMe
SO2Bn

HN
R

MeONa

AcOH

O 2N

Ph

O O

NO2
81

H
N

82

R = H, NO2

3--3,4--2-1,4--4- 83 [74]
56% 2-(2-)a ( 27).
27
O O
S

O
S
O
NO2

Hg
300 mV
H2SO4
83

N
OH

NH H2SO4

84 ,
, [75] 3-(3',4',5'-)-7R-3,4--1,4--1,1- 85, ( 28).
318

InterBioScreen

28

OMe

OMe
OMe
OMe

OMe
H
N

CH2=SO2

N
R

OMe

S
O O

R
84

85

[2,1-c][1,4] [7682]. , 1-(-)2- 86 87,


88
, .

89,
[2,1-c][1,4] 90 ( 29).
29
O
N
F

Ph3P

Ar
ArMgBr

86

Ar

i-PrO2CN=NCO2Pr-i

OH

MeONa

AcSH

87

SAc NaH

88

R"
N
N
S
89

R'

H
N

R'
R"

HCHO

N
S

90

, 2

319

1,4-
91
[83]
92, 2-R-3--2-1,4- 93. :
92,
93 ( 30).
30
S

Cl

OAlk

AlkONa

OAlk

92

91

93

R = H, Me, Ph;
Alk = Me, Et, i-Pr, t-Bu

3- 94 2%-
7075% [84] 2-4-1,4--4- 95. 96
( 31).
31
S
+

Br

94

Ar

S
H2O

O
Ar

OH
Ar

2% NaOH

N
O

H
95

96

2- 97
98, [85] 2--2,4--2-1,4--3(4)- 99 ( 32).
32

O CF3SO3Me

H2O

N
S

O
OH

F3CSO3
97

320

98

99

InterBioScreen

5-(2-)-3--2-(4-)-2,3,4,5--1,5--4- 100
[86] 2-(-4-)-4-(2-)-2-1,4--3(4)- 101
E- Z-.
2-(4-)-4-(2-)-2-1,4--3(4)
102 ( 33).
33

OMe

OMe

OMe

S
OH
N

100

SOCl2

Bu3SnH

Cl
O

O
N

102

101

-
[87] 14-1--4--6--(3)-1,2,3- 103
9%
96.8% 7-5--3,4--3- 104 ( 34).
34
O

NH2 S Cl
2 2

N
Cl
103

S
S
OH

Cl

H
N

ONa
NaOH

Cl
104

1,4-

2--7R-2-1,4--3(4)- 105 [88]
1,4- 106, ( 35).
, 2

321

35
R

Cl

N
H

105

R'

H
N

R"

R'
N

S
N
H

R = H, Cl, OMe, CF3; R', R" = H, Alk

R"

106

2--1,4--3(4)-
N- [89] 2--2-1,4-3(4)-. , 107
1-(4--2-)
2-[4-(4--2-)]-2-1,4--3(4)- 108, [90]
( 36).
36
N

H
N

H
N

Br
( )4

N
( )4

107

108


(3,4--3--2-1,4--2-) 109 2--5- 110
[91] 111 ( 37).
37

R'

R"

N
H

Br

OEt

R'

R"

OEt

+
O

O
S

N
109

322

110

111

InterBioScreen

1,4- 112 [92] 113.


N- 114 ( 38).
38

R'NCO

NaNO2

O
112

113

HCl

N
H

N
R'
N
NO

NH
R'

114

R = H, Cl; R' = Et, 4-ClC6H4

2-3,4--1,4--2,3
115.
[93] 116.
- 117 ( 39).
39
O

O NH NH
2
2

O
OEt
O

115

ArCHO

O Cl

Cl

HN

116

Ar

HN
O

Ar
Cl

117


3,4--2-3--1,4- 118 119,
120. [94],
- ( 40).
, 2

323

40

Ar
S
N
R

R' i-Pr NLi


2

N
R

118

R'

ArCHO

N
R

OLi

119

OH

R'
O

120

3,4--4--3--2-1,4- 121 2- 3- 122, [9598]


. 122
1,5- 123,
[99102] ( 41).
41

OR
R'
SH

Alk
NH

R'

O
OH

Cl

N
Alk

X
X

ArCHO

MeONa

OH

N
Alk

121

R'

S
H2O

N
Alk
122

R'
O

OR
R'

OR
R'

Me3SiCl
H2O2

S
O
X

N
Alk

O
123

1,4-
2-R-2,3-[1,2,3-de][1,4]-3- 125 2-R-3-[1,2,3-de][1,4]324

InterBioScreen

-S,S- 127 [103]


124 126
96% ( 42).
42

R'

N
H

R'

RO

N
H

R'

R'

O
OR

O O
R'
S

H 124

R' = H, Ph

O O
R'
S

O O
R'
S

Ph

125

Ph

O O
S
R'

Ph

Ph

RO

OR
R' = H, Me, Ph

127

126

128 129. 4-2-4--1,4- 128 (R = Ph) [104]


130 (R' = H). , 1 1-9--3--1,9-[b][3,4-e][1,4] 130 (R' = COCH3)
( 43).
43
NH2OH

O
N

129

R'
N
N

S
128

NH2NH2

S
129 R = Me, Ph; 130 R = Ph, R' = H, Ac

130

, 2

325

2-(3--3,4--2-1,4--4-) 131


132 (R, R' = H, Cl, Me, NO2) [105] ( 44).
44
R

R'

R'

MeONa, MeOH
AcONH4, AcOH

O
N

131

132

N
N
H

R, R' = H, Cl, Me, NO2

3--2--2-1,4- 133 (R'' = R''' = H) c


- 134.
42% [106] 4--4-[b][1,2-d][1,4]-2- 135. [107], -1,4-
( 45).
45
R"

OR

R"

R'"

NH2

R'"

Br

134

R"

OR

NH2
O

R"'

N
OR'

O
133

OR

OR'
135

138
[108, 109] 1,4- 136 137 -
( 46).
326

InterBioScreen

46
O
HN
R
NH2

S
R'
N

S
R'

R'

N
N

137

136

NH
HN

138

141, , [110] 3--2-1,4- 139 1--4-[b][1,2,4][4,3-d][1,4]


140 ( 47).
47
H
N

O
Cl

S
R
N

Cl

R
N

NH
NH2

Cl

139

S
R
N

N
N

140

N
N

N
141

R = H, Cl, CF3, NO2; X = O, NMe

-1,4 142

[111] 4-[b][1,2,4][4,3-d][1,4]-1- 143.
5374% 144 ( 48).
48

R'
R

R'
S

NH
NH

N
H2 N
142

R'

Cl

NH3

N
HS

N
N

OEt R

KOH, T

143

, 2

N
O
S
EtO

N
N

144

327

3--3,4--2-1,4- 145
31% 146.
[112] 11b,12-[5,6][1,4][3,4-a]
147 ( 49).
49
Br

S
N
H

EtO

OEt

NaH

Ph

TosOH
AcOH

Ph

EtO
OEt
146

145

147

148
149 N,N-
150.
[113] 4--3,5-[b][1,6-d][1,4]-3-
152, 150 (Ar = 4ClC6H4) () 5060 64% 4-(4-)-3,5--2-[b][4,3-e][1,4]-3- 151
( 50).
50

S
N
H

Ar
CN

OEt

Ar

N
H

NH2

O
150

149

N
N

N
S
N
H

328

Ar
O

OMe
N

EtO

N
H

148

+
H

N
N

Ar

S
N
H
151

NH
O
Ar

InterBioScreen

S
N
H

O
N

Ar

Ar
150

152

3,4--3--2-6-1,4- 153
[114] 1,2,3,4-[5,6][1,4][4,3-a][1,3,5] 154, ( 51).
51

S
X

RNCO

N
H

N
154 R

O
153

R = Me, Et, Bu, Ph; X = H, Cl

R
O

3--7-R-2H-1,4- 155

2849% [115] 2--8-R-1,5-[5,6][1,4][3,4-c][1,2,4] 156 ( 52).
52

N
S

R
155

NH2
NH

Cl


R = H, Cl

N
N

S
156

2--3(4)- 157
(5--4,4,5,6--2-[][1,2-a][1,4]-11-) 158 [116118].
159 (Hal = Cl, Br). 158 (R = H) -2--3(2)- 160, , 2

329


1,2- 161 ( 53).
53

N
S

O
Cl
R

R'

R"

O NaBH4
R

AgClO4

ClO4

R'
R"

R'
R"

157

160

158
HHal

hv

O
R

O
O

S
R'

Hal

O
R'
R"

R"
161

159

2- 162 (R' = Me, Et,


Me2CH), , [119] 163
( 54).
54
H
N

R'Hal
NaH

S
O
162

N
+

S
R'

O
163

R = H, Br, OMe; R' = Me, Et, i-Pr

330

InterBioScreen


1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.

Brown C., Davidson R.M., Adv. Heterocycl. Chem. 1985 38 135.


Santacroce C., Sica D., Nicolaus R.A., Gazz. Chim. Ital. 1968 98 85.
Watanabe Masanori, 90 264 768; Chem. Abstr. 1991 114 143434c.
Gupta R.R., Kumar R., Gautam R.K., J. Heterocycl. Chem. 1984 21 1713.
Gupta R.R., Kalwania G.S., Kumar R., Bull. Chem. Soc. Jpn. 1984 57 2343.
Gupta R.R., Kumar R., Heterocycles 1984 22 (1) 87.
Gupta R.R., Gautam R.K., Kumar R., Heterocycles 1984 22 (5) 1143.
Niemers E., Gruetzmann R., Mardin M., et al., 3 229 121;
Chem. Abstr. 1984 100 209852.
Gupta R.R., Kumar R., Gautam R.K., Phosphorus, Sulfur Silicon Relat. Elem. 1985
24 301.
Gupta R.R., Gautam R.K., Pharmazie 1985 40 (3) 203; Chem. Abstr. 1985 103
87828.
Gupta R.R., Kumar R., Ann. Soc. Sci. Bruxelles 1984 92 (23) 145; Chem. Abstr.
1985 103 122787c.
Alyea E.C., Malek A., J. Heterocycl. Chem. 1985 22 1325.
Gupta R.R., Kumar R., Gautam R.K., J. Fluorine Chem. 1985 28 381.
Gupta R.R., Kumar R., Synth. Commun. 1987 17 (2) 229.
Ojha K.G., Adwani P., Mathur N., Orient J. Chem. 1991 7 (3) 135; Chem. Abstr.
1992 116 21010.
Gupta R.R., Rathore R.S., Jain M., Saraswat V., Pharmazie 1992 47 (3) 229.
Rathore R.K., Rathore R.S., Gupta R.R., Pharmazie 1991 46 (5) 354.
Gupta R.R., Rathore R.K., Gupta V., Rathore R.S., Pharmazie 1991 46 (8) 602.
Mathur N., Adwani P., Ojha K.G., Pharmazie 1992 47 (12) 944.
Adwani P., Mathur N., Gupta V., Ojha K.G., Asian J. Chem. 1993 5 (2) 467;
Chem. Abstr. 1994 120 323432.
Rathore R.K., Gupta V., Jain M., Gupta R.R., Indian J. Chem., Sect. B 1993 32
(3) 370.
Bhatnagar D.D., Gupta K.K., Gupta V., Heterocycl. Commun. 1994 1 (1) 77.
Rathore R.K., Saxena C., Gupta R.R., Egypt. J. Chem. 1993 35 (6) 735;
Chem. Abstr. 1995 122 81310.
Hamadi M.Y., Gupta R., Gupta R.R., J. Fluorine Chem. 1999 94 169.
Gupta R., Verma P.S., Gupta R.R., Heterocycl. Commun. 1998 4 (5) 479.
Paul S., Gupta R., Loupy A., et al., Synth. Commun. 2001 31 (5) 711.
Trapani G., Latrofa A., Reho A., Liso G., J. Heterocycl. Chem. 1989 26 (3) 721.
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Adwani P., Mathur N., Gupta V., Oiha K.G., Pharmazie 1991 46 (12) 883.
Verma P.S., Gupta R., Sharma N., et al., Heterocycl. Commun. 1999 5 (1) 93.
Chaudhari B.R., Shinde D.B., Shingare M.S., Pol. J. Chem. 1996 70 (10) 1250;
hem. Abstr. 1997 126 47170.
Cabiddu S., Floris C., Melis S., et al., J. Heterocycl. Chem. 1986 23 1815.
Gupta R.R., Gautam R.K., Kumar R., J. Heterocycl. Chem. 1987 24 171.
.., .., .., 2002 (3) 399.
Grandolini G., Perioli L., Ambrogi V., Gazz. Chim. Ital. 1997 127 (8) 411.
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, 2

331

37. Henning R., Lerch U., Kaiser J., 3 347 173; hem. Abstr. 1986
104 88571.
38. Fujita M., Ota A., Ito S., et al., Synthesis 1988 599.
39. 389 112; hem. Abstr. 1990 112 235330.
40. 389 113; hem. Abstr. 1990 112 235331.
41. Fujita M., Ito S., Ota A., et al., J. Med. Chem. 1990 33 1898.
42. Iwao J., Iso T., Kawashima Y., 88 104 969; hem. Abstr. 1990
112 7476.
43. Fujita M., Ito S., Suhara H., et al., Yakugaku Zasshi 1991 111 (1) 59; hem. Abstr.
1991 114 228857.
44. Yukimoto Y., Iwase M., Nagasaki M., 92 120 067; hem. Abstr.
1992 117 171463.
45. Fujimura K., Fujita M., Suhara H., et al., Bioorg. Med. Chem. 1994 2 (4) 235;
hem. Abstr. 1994 121 133310.
46. Shirasawa E., Kageyama M., 95 133 225; hem. Abstr. 1995 123
123157.
47. Tomita K., Araya M., 96 319 237; hem. Abstr. 1997 126 126916.
48. Okami Y., Kawashima Y., 9 712 576; hem. Abstr. 1997 126
171612.
49. Kawashima Y., Ota A., Araki Y., Shii D., 97 100 418;
hem. Abstr. 1997 127 34231.
50. Selvi S., Perumal P.T., Synth. Commun. 2001 31 (14) 2199.
51. Takahashi M., Ohba M., Heterocycles 1995 41 (10) 2263.
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53. Miyakoshi T., Hishama H., Yoshida M., 97 124 626; Chem. Abstr.
1997 127 34228.
54. Mustafa E.M., Takaoka A., Ishikawa N., Heterocycles 1986 24 (3) 593.
55. Rao M.H., Reddy A.P.R., Veeranagaiah V., Synth. Commun. 1991 21 (17) 1715.
56. Konishi H., Takishita M., Koketsu H., et al., Heterocycles 1986 24 (6) 1557.
57. .., .., .. ., 1990 26 (6) 1345.
58. .., .., .., .-. . 1992 26
(2) 38.
59. .., .., . . . 1996 62 (78) 47.
60. .., .., .., . . . 1992 58
(8) 682.
61. Benz G., Fengler G., Meyer H., et al., 3 426 564; Chem. Abstr.
1986 105 60620.
62. Zhong W., Chen X., Zhang Y., Heteroatom Chem. 2001 12 (3) 156.
63. Combs D.W., Rampulla M.S., Demers J.P., et al., J. Med. Chem. 1992 35 (1) 172.
64. Matsuoka H., Ohi N., Mihara M., et al., J. Med. Chem. 1997 40 (1) 105.
65. Lopez S.E., Charris J., Urdaneta N., Lobo G., Phosphorus, Sulfur Silicon Relat.
Elem. 1998 143 53.
66. .., .., .., .., 1998 34
(3) 455.
67. Vysokov V.I., Charushin V.N., Afanasyeva G.B., Chupakhin O.N., Mendeleev
Commun. 1993 (4) 159.
332

InterBioScreen

68.
69.
70.
71.
72.
73.
74.

Culbertson T.P., J. Heterocycl. Chem. 1991 28 (7) 1701.


Cecchetti V., Fravolini A., Schiaffella F., et al., J. Heterocycl. Chem. 1992 29 375.
Cecchetti V., Fravolini A., Schiaffella F., Synth. Commun. 1991 21 (22) 2301.
ecchetti V., Fravolini A., Fringuelli R., et al., J. Med. Chem. 1987 30 465.
Jpn. Patent 85 208 987; hem. bstr. 1986 104 207290.
Gerasyuto A.I., Zlotin S.G., Semenov V.V., Synthesis 2001 (2) 300.
Matschiner H., Biering H., Schilling H., et al., 220 345;
hem. Abstr. 1986 104 88572.
75. Manrao M.R., Kanta C., Kalsi P.S., J. Indian Counc. Chem. 1994 10 (2) 23.
76. Campiani G., Nacci V., Garofalo A., et al., Biomed. Chem. Lett. 1992 2 1193.
77. Nacci V., Campiani G., Garofalo A., et al., Synth. Commun. 1990 20 3019.
78. Nacci V., Campiani G., Garofalo A., J. Heterocycl. Chem. 1990 27 1329.
79. Campiani G., Garofalo A., Fiorini I., et al., Biomed. Chem. Lett. 1994 4 1235.
80. Campiani G., Garofalo A., Fiorini I., et al., J. Med. Chem. 1995 38 4393.
81. Corelli F., Manetti F., Tafi A., et al., J. Med. Chem. 1997 40 125.
82. Sanchez I., Pujol M.D., Tetrahedron 1999 55 (17) 5593.
83. Florio S., Capriati V., Colli G., Tetrahedron 1997 53 (16) 5839.
84. Singh H., Singh D.J., Kumar S., Indian J. Chem., Sect. B 1992 31 (4) 217.
85. Owen T.C., Doad G.J.S., J. Chem. Res. Synop. 1990 (11) 362.
86. Erker T., Bartsch H., Liebigs Ann. Chem. 1992 (4) 403.
87. Ookubo S., Ookuma T., Ito N., 9 641 042; Chem. Abstr. 1996
124 343321.
88. Chihara Y., Setoguchi S., Yaoka O., PCT Int Appl. WO 8 403 700; Chem. Abstr.
1985 103 54090.
89. Kajino M., Mizuno K., Tawada H., et al., Chem. Pharm. Bull. 1991 39 (11) 2888.
90. Jasserand D., Floc H.F., White R., 4 037 427; Chem. Abstr. 1992
117 90326.
91. Aotsuka T., Hosono H., Kurihara T., et al., Eur. Appl. EP 492 667; Chem. Abstr.
1992 117 151006.
92. Rai D., Gupta V., Gupta R.R., Heterocycl. Commun. 1996 2 (3) 273.
93. Hogale M., Uthale A., Proc. Indian Acad. Sci. 1990 102 (4) 535; Chem. Abstr. 1991
114 101880.
94. Babudri F., Florio S., Zuccaro L., et al., Tetrahedron 1985 41 (3) 569.
95. Kawashima Y., Ota A., Mibu H., PCT Int. Appl. WO 9 405 647; Chem. Abstr. 1994
121 108814.
96. Kawashima Y., Ota A., Mibu H., 9 473 033; Chem. Abstr. 1994
121 83354.
97. Kawashima Y., Ota A., Mibu H., Matsubayashi K., PCT Int. Appl. WO 9 513 269;
Chem. Abstr. 1995 123 198818.
98. Kawashima Y., Ota A., Morikawa Y., Mibu H., Eur. Appl. EP 657444; Chem.
Abstr. 1995 123 169638.
99. 83 180 476; Chem. Abstr. 1984 100 85732.
100. 8 572 876; Chem. Abstr. 1985 103 178283.
101. Maki Y., Sako M., Mitsumori N., et al., 4 490 292; Chem. Abstr.
1985 102 132086.
102. 8 572 875; Chem. Abstr. 1985 103 142032.
103. Armenise D., Trapani G., Arrivo V., et al., J. Heterocycl. Chem. 2000 37 1611.
, 2

333

104. Sugiyama K., Yamashita M., Takamatsu M., Chem. Pharm. Bull. 1984 32 (4) 1593;
Chem. Abstr. 1985 102 6368.
105. Kuroki M., Ayabe S., Nishiyama H., Miyakoshi T., 98 130 274;
Chem. Abstr. 1998 129 41139.
106. Kuroki M., Ayabe S., Nishiyama H., Miyakoshi T., 98 130 273;
Chem. Abstr. 1998 129 41138.
107. Macchiarulo A., Costantino G., Fringuelli D., et al., Bioorg. Med. Chem. 2002 10
(11) 3415.
108. Shridhar D.R., Jogibhukta M., Vishwakarma L.C., Indian J. Chem., Sect. B 1984
23 445.
109. Shridhar D.R., Jogibhukta M., Joshi P.P., et al., 153 687;
hem. Abstr. 1985 103 178269.
110. Grandolini G., Tiralti M.C., Rossi C., et al., Farmaco, Ed. Sci. 1987 42 (1) 43.
111. Ambrogi V., Grandolini G., Perioli L., et al., Eur. J. Med. Chem. 1991 26 (8) 835.
112. Armenise D., Trapani G., Arrivo V., Morlacchi F., Farmaco Ed. Sci. 1991 46
(9) 1023.
113. Chorvat R.J., Radak S.E., Desai B.N., J. Org. Chem. 1987 52 1366.
114. Musser J.H., Lewis S.C., Bender R.H.W., Heterocycles 1990 31 (8) 1393.
115. Perioli L., Ambrogi V., Grandolini G., et al., Farmaco, Ed. Sci. 1994 49 (4) 245.
116. Kataoka T., Nakamura Y., Matsumoto H., J. Chem. Soc. Perkin Trans. 1 1997
(3) 309.
117. Kataoka T., Iwama T., Matsumoto H., et al., Chem. Pharm. Bull. 1998 46 (1) 148.
118. Iwama T., Matsumoto H., Ito T., et al., Chem. Pharm. Bull. 1998 46 (6) 913.
119. Iskander G.M., El Khawad I., Zahran H.B., J. Prakt. Chem. 1989 331 (1) 82.

334

InterBioScreen

1,3-

-, -
.., ..
,


- .

- ,
,
[14].
1,3-
, ,
. ,
1,3- ( ).
1,3- ,
1,3- , 1,3-, -, 1,3-, 1,3-
,
. , 1,3-
:
1. , 1,3-
-2,4- 1, 4--6--2 2, 4--6--1-(3,4,5-)-1,2--2 3,
1,3- 4.

HO

O
O
1

OH

O
2

O
N

O
O
O

N
O

2. , 1,3- 3-(2-)-3- 5, (2-)-1- 6, 4,4,4--1-(2-)-1,3- 7, 1,3-(3-)- 8.


, 2

335

O O
O

O
S

CF3

3. , 1,3- 9, 10, 11, -S,S- 12 .

S
O
CF3

10

N
O

S
N
11

NH2

O
12

, 1,3-

,
(Derwent World Drug Index
World Drug Alert), 1,3- 300
[1]. , 4-2- : ( 13, 14); ( 15); ( 16, B 17,
18); ( 19).
2- , 20, .
, .
21 N 22
.
336

InterBioScreen

OH
O
O

O
O

OH
15

13

OH

O
OH

H
N

14

O
O

OMe
OH

H
O

OMe OMe O

OMe O
O

H
O

17

16

OH

18

R
HO

O
N

OMe

OMe

CN

CN

HO

O
N

HO
19

20

21

22


26, 27 - 4--6--2- 2 23
- 24 25 [57] ( 1).
, 2

337

24

O
R'

OH

R'

X
O

2, 23

25

26, 27

X = O, NH; R = Ar, Alk

29
(-) 28 [8, 9] ( 2).
2
O

OLi

Cl

Cl

29

28

3-[3,2-] 32 , - 31 4- 30. 4-[3,2-] [10] ( 3).


3

R'

OH

R"

OH

R"

31

R'

NO2

NO2

30

R'

R"

R
O

32
R = 3,4,5-MeOC6H2, 2,4-MeOC6H3, 4-MeOC6H4; R', R" = H, Ph

338

InterBioScreen


1,3- 4 33, 34,
35 36
[11] ( 4).
4
R"

R'

R"

R'

33

R'

R"
R"

N
O

R'

35

R"

R'
34

R"

N
O

R'
O

N
36

, . ,
37 4--2- 38, 39,
40 [12, 13] ( 5).
5

CN

NC

CN

NC
OH

OH
R'

CN
CN

R'

+
CN

NC
37

R''

R''

38

39

R'
R''

O
NH2

O
O

NH2

40
R', R" = Ph; R' = H, R" = Me

, 2

339


3- 41 (NC)2CHNa+ 42,
43 44 [14]
( 6).
6

O
O

NC
O

42

CN

CN
O

Br

NH2

OH

41

44

NC
CN
43


, , .
[15] 6--4-[3,2-]-4- 47 45 ArCOCH3 46 [15] ( 7).
7
O

O
HO

S
S

NC

46

HO

Ar
S

NC

45

340

InterBioScreen

HO

HO

Ar
S

NC
S

OH

NC

Ar
47

49 50
S,N- 48 1 1,3--2-
.
- [16] ( 8).
8
O

NH

O
1

O
S

Ar
Ar

S
S

H
O
S

49

S
Et

HN

NH
O

48

Et

Ar

H
N Et

N
Et

50


51, 52 1,3- , , 4 [17] ( 9).

CN

N
O

N
4

O
H

N
O

Cl

NH2

N
O

O
OEt

51

Cl

OEt
SH

N
O

OEt

52

, 2

341


.
"" 1,3- . ,
4-()-3,5- 53 [3,4-d]4- 54 [18]. [3,4-d] 55,
[3,4-d]-4- 56 [1820] ( 10).
10

OH

N
S

R
OH

R
N
N

C5H11

RNHNH2

53

N N

R
N
N

C5H11

R'
O

R'

54

56

55
R, R' = Me, Et, Ph

-.
57 ( 11)
58,
[1,2:6,7][4,3-c] 59 [21].
11
H2N

OH
S

342

58

NH
N

57

59

InterBioScreen



. 60 61
[4,3-d]-4- 62 [18] ( 12).
12
O

NH2OH
61

N
S

60

O
62

63 64
65 [22] ( 13).
O
F3C
HO

O
O

EtO

Cl

EtO
O
S

EtO

O
CF3

13

OH
N

Et3N

CF3

O
63

64

65


66, 67
68, 69 [2325] ( 14).

OEt

O
Ar

NC

N
N
Ar

NH2OH
MeOH

Ar

N
H

OH

68

69

NC

O
N

O
O

14
O

O N
N

OH

Ar
N

67

66

OH

N
H

, 2

O
O

343


1,2,5- 70 100 [26] ( 15).

N
S
N

H2 N
F 3C

15

CF3
O
S

71 (28%)

70

2H-
2H- , 2H-.
1. - 72 ( ) [27, 28] ( 16).
16

R'

O
R

N
72

CN

OH

R
R'

R'

CN

OH

R = H, Me; R' = COMe, CONHPh, Ar, Het, CN, COPh, SO2Ph, CONH2, CSNH2

73
( 17), , .
[2,3-] [28, 29].
17
HO

O
H

OH

Cl

73

344

HO

CN

OH
R

CN

OH

R = COMe, , , CN, COPh, SO2Ph, CONH2, CSNH2

InterBioScreen

2. [1,2-b]-2-, [3,2-]2-, [3,2-][1]-2-, [3,2-][1]-2,5-,


[3,2-]-2,5- [3034] 3- 3--2,4- 74 ( = ) [30] ( 18), 75 [35] ( 19), 76 ( = ) [34]
4--2- 76 (X = NH, NMe) [31, 36] ( 20) . -
.
2- 28% 93%.
18

R'

R"

R"

R"

R'

CN

OH

R"

CN

R"

R"

74

O
R'

X
O

R"

NH

+
H

R'

X
O

R"

R"

R"

R = CO2Me, CO2Et, CONHPh, Ar, CN, SO2Ph;


R', R'' = Ph, H, Me; X = CH2, NH, NMe, NCHO, O

19
O
R
O

R'

O
R

+
N
R

N
R"

R"

N
N
R

75
R = H, Me, Ar; R' = Me; R'' = CN, CO2Me, COPh;
X = O, NH, NMe [35, 36]

, 2

345

20
O

+
X

R'''

R'

N
R"

76
R = H, Me, Ar; R' = OEt, NMe2; R'' = CN, CO2Me, COPh;
X = O, NH, NMe

3.
, 77 [37] 1,3- 78 ( 21).
21
O

R'
O

O
O

R'

X
OH

R'

R'

R
77

OH

78

,
2- ,
-- [38]. 6-4--2- 79 80
4--2,5- 81, 82.
82 83 ( 22)
[3943].
22
O

Cl

+
OH
79

346

O
O
Cl

O
O

80

OH
81

InterBioScreen

O
O

O
O
O

OH

OH
O

O
O

82

83

4. , 1,3- . , 84 85 86 [4446] ( 23). [47].


23
O

O
R'

O
R'

R
O

OMe

R'

85

NH2

86

84

5. 2--3- 87 [4850] ( 24).


24

R
NH

O
NH

R'

87

O
R"
O

R
NH

N
N
R"

OR

R
NH
O

O
O
HN
N

R
NH
O

R"'
R = COMe; R', R" = Ph; R" = Me, Et

, 2

347

6. - 1,3- [51, 52]


( 25).
25

O
O
R'

OEt

R''

O
O

X = NH, NMe, NPh, O

4-
4- ,- 1,3- , 4- -, - [5360] ( 26).
26
R'

O
H2 N

HO

NH2

R
R'

NH2
O

NC

R'
O

R
X

R'

R
R'

NH2

NH2
R

R'
O

H
N

HN

NH2
R

R'

R = CN, CO2Me; R' = lk, Ar, Het; X = O, NH, NR

348

InterBioScreen


.

1,3- 2-(, ) 88 [6163]
( 27). 1,3-, 1,3- 1,3-. 88 (X = S) 1,3- 4,6- 3--2(1)- .
27
R'
R'

R
O

CN

X
NH2

N
H

CN
88

R = R' = 2-C4H3S, 3-C5H4N, 4-C5H4N; X = O, S, Se

1,3-
.
, 2-, 1-(3-)- 1-(4-)1,3-
2-(1)- [6468] ( 28).
28

R
O

R'

R'
O

R
CN

CN

CN

NH2
R

N
H

R'

N
H

R = Me; R' = 2-C4H3S, 3-C5H4N, 4-C5H4N; X = O, S

, 1,3-
, . , , 6-(-2)-4-2-(1)- - [69, 70] ( 29).
, 2

349

29

CF3

CF3

CF3

OMe

CF3
CN
X

N
H

X = O, S

- 89 - 90 -,
6--3--2(1)- - 91 [7175]
( 30).
30
CN

O
R
R'
89 R' = ONa;
90 R' = NMe2

NH2
CN

N
H

91

R = 2-C4H3S, 3-C4H3S, 3-C5H4N, 4-C5H4N, 2-C4H3O; X = O, S

- 5,6--3--2(1)-. , 5-()-6--3--2(1)- 92, ,


1-()-1--2- 93 ( 31). - [76].
350

InterBioScreen

31
O

O
O

+
MeO

CN

NH2

CN
N
H

OMe

93

92

94 4-()-3-(4-)-2-
- [77]
( 32).
32
O

NC

CN

CN

NH2

N
H

CN

94

95
3-(4-)-4--2- [78] ( 33).
33
S

NC

OEt

N
NH2

CN
N
H

95

() 96 N-, 5-(2-)-6--3--2- N- 97, 98 [79] ( 34).


, 2

351

34

O
F 3C

S
CN

OEt
96

F 3C

97

CN

F 3C

N
H

98

1,4- 1,3-
, -, -, .
..
[62, 63].
.
(, , ,
) . [63].
[63].
99 100,
2- 101 ,
[80] ( 35).
35

ONa
N

S
CN

NH2

CN

N
N
H

O
99

100

CN

N
N

101


- 102 [62, 63] ( 36). ,
,
- [81].
352

InterBioScreen

36
X

CN

Y
R'
R"

NH2

Y
R'
R"

NH2

CN
N
H

R"'

R'
R"

102
Y = O, S, NMe, NBn; X = O, S; R = ONa, C6H10N;
R"' = COMe, CONHPh, CO2Me

103 89 3-()[3,4-c], 5,6,7,8-, 2,7- [8287]


( 37).
37
R
O

Y
R'
R"

NH2
CN

NH

Y
R'
R"

X
CN

89

103

Y = O, S, NMe, NBn; X = O, S; R = Alk, Ar, Het; R' = R'' = Me, H

- ,
- , - [72, 8891].
-2,4- 104
( ), [3,4-b]1- 105 51% 90% [92] ( 38).
38
Ar
O

NH2
104

Ar

R
O
O

N
105

R = H, Cl; Ar = Ph, 4-MeC6H4, 2-FC6H4

, 2

353

-

[93100] ( 3941).
39

O
N

R'

+
NH
R

O
R'

N
N
R

R'

NH

N
R

R = Bn , CH2Bn; R' = CO2Me, CO2Et, CONH2

40
NC

CN

MeS

O
R'

SMe

R'

R"

CN

R'"

N
R

R'

N
MeS

CN

R'

SMe

N
R

R"

SMe

R'"

NH2

CN

O
O

NH2

N
R

NH2

N
N
R

NH2

SMe

R, R' = Me, H; R'' = Ar, Het; R''' = CO2Me, CO2Et, SO2Ph, CN

41

O
R'
O

R"

R"'

+
N
R

NH2

R'
CN

R"

N
N
R

NH2

R, R' = Me, H; R'' = CO2H ,CO2Me, CO2Et, CONH2, CN; R"' = CHO, NMe2

354

InterBioScreen

N--3--4- 106 107 7-1--4--3--5,6--8-2,7- 108 [98] ( 42).


42
CN

OMe

ONa

OMe
106

NH
OH

OMe

107

NH2
O

NH
108

OH

R = Bn, Et


. ,
1,3- ( ) 1,4,5,6,7,8--1,6- 109, [100] ( 43).
43

O
O

H
Ar

HN

OMe

+
O

Ar

HN

H2 N

O
OMe

N
H
109


1,3-

, 2

355

. 110, 111,
,
112 113 [101, 102] ( 44).
44

O
R

R'
H

N
N

O
N

N
Ar

110

NH
Ar

111

O
R'

R
N

R'

CN
NH
Ar

112

N
Ar

NH

113

R = 2-C4H3S, 2-C4H3O; R' = CN, CO2Et;


Ar = Ph, 4-NO2C6H4, 1-

, N--3(2H)-,
[103] ( 45).
45
O

OH

OH

OH O
R

EtO
N

N
Ar

N
Ar

N
N

O
O

Ar

OEt

R = Me, Ph, Bn; Ar = Ph, 4-ClC6H4, 3,4-ClC6H3, 2,4-ClC6H3

1--3--6--4- 116 115,


4--6--2- 114 .
117 [104] ( 46).
356

InterBioScreen

46
O

OH

114

O
115

HN
N
O

Ar

OH
N
Ar

O
RNH2

116

N
Ar

NH
R

117 (61%)

-
1,3-
.

. .. (InterBioScreen)

[1].

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.

Daylight Chemical Information Systems, WDI 001 & WDA Database Version 4.73,
2000. Los Altos, CA, USA. http: // www.daylight.com.
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28. Saint-Ruf G., De A., Brunskill J.S.A., Jeffrey H., J. Heterocycl. Chem. 1980 17
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55. Shaker R.M., Pharmazie 1996 51 148.
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358

InterBioScreen

57. Yakout E.M.A., Ibrahim N.M., Ghoneeim K.M., Mahran M.R.H., J. Chem. Res.
Synop. 1999 11 652.
58. Abdel Hafiz I.S., Hussein A.M., Mahmoud V.F.R., Z. Naturforsch. B, Chem. Sci.
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1988 805.
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76 113242.
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81. .., .., 2000 (4) 567.
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. 1989 42 505.
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Sulfur Reports 1992 13 (1) 1.
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91.
92.
93.
94.

.., .., . , . . 2000 (2) 347.


Schmidt D.-G., Seemuth P.D., Zimmer H., J. Org. Chem. 1983 48 (11) 1914.
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(48) 8295.
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96. Ivanov I.C., Stoyanov E.V., StoyanovaDenkova P., Dimitrov V.S., Liebigs Ann.
Chem. 1997 (8) 1777.
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104. Wiley R.H., Jarboe C.H., J. Am. Chem. Soc. 1956 78 (2) 624.

360

InterBioScreen


4,5- 2,3--2,3-
.., ..

614600, , . , 15
2,3--2,3- ()
1967 .
. [1], 4--5-- 1
.
[2], . ,
. , 4, 5
.
1. 4,5- 2,3--2,3-
1.1 2,4-
.
,
.
3- 1,
[3] [4], 5--4-- 2 [3, 4]
( 1).
1

OEt

MeONa

OEt

EtO

O
O

AlkOH

OAlk
O

OAlk

MeI

K2CO3

R
2

R = H, Me, MeO, Cl

, 2

361

2-[]-1- , []-2- ,
[3,4][1,2-b]-2,3- 3 [5] ( 2).
2
O
AlkO

O
OAlk

AlkOH

AlkONa

O
O

OAlk

O
3

1.2

4 () [69] ( 3),
.
3
Ar

Ar
O

Si

Cl

Cl

O
O

O
4

, , 4, 5, 6 [9]
( 4).
4
O
Ph
R'
O
R

Si

Cl

Cl

R = Ph
R' = Bn

O
O

R+R' = (CH2)4

362

Ph

O
6

InterBioScreen

1.3 - -

4,5- , .
7 [1] ( 5).
5
O
O

Ph

Ph

Cl

Cl

Ph

Ph
O
O
7

2-, 5-(-)-4-- 8
[11] ( 6).
6

O
Cl

OH
O

O
O

O
O

Cl

Cl

Cl
O

Cl

OH

O
8

O
O

Cl

O
O
O

O
2

, 2

363

- -
9 [12, 13]. [12] ( 7).
7
O
O

O
R

R'

Cl

Cl

MgCl2

R'

O
O
O
9

;
S
R = R' = R"R"'N, R", R"' = Alk, Ph
R = Alk, OAlk; R' = Alk, Ar,

N,N- - 10
11 12 [12], 5-
12 2,5--2- 13
( 8).
8

R'
R'

R
O

R'
O

R'
N

Cl

Cl

10

11

R'
N

O
R

O
R'
N

R'
O

12

OH
R = Me

R'

O
13

R = Me, Ph; R' = Ph, Bn

1.4 2,3--2,3-
5-- 14 5-4-- 5--4-- 15 [14] ( 9).
364

InterBioScreen

9
Hal
Ar

Hal2

Ar

HHal

O
14

O
O

15 O

1.5 , 2,3--2,3-
2--1--1,3-
4--5--2,3- 16, 4-5-- 17 [15] ( 10).
10
Ph
Br

CO

Ni(CN)2

Ph

Ph
SiO2

16

17

4--5-- 1 , 4-[-()]-5-- [13, 1618].


[4+2], [2+2] [17].
3.3.
1.6
18 5--4-(3--2-)- 19; 20
[10] ( 11).
11
61C

100

Ar

+
N
H
18

Ar

Cl

Cl

N
19

20C
5
Ar = Ph

Ar

O
O

Ar
Ph

Ph
Cl

O
20

, 2

O
365

-() 21 2,3-(2--4,5--4,5--3-) 22 ( 12).


12

O
H
N

+
N
H

O
2
Cl

Cl

O
4HCl

Ph
Ph

Ph

Ph

22

21

2. - 4,5-
4--5-(-)-
[12] ( . . 1).

O
Cl

1.386

OMe
1.46

1.215
1.254
1.398
1.182
O
1.395 O

OMe

107

112.7

O
103.5

Cl
O
108.7

O
127.1

. 1. () (.) 4--5-(-)-2,3--2,3-

4,5- (= = 17801845 1),


(= = 17101735 1), (4) [4, 6, 7, 11, 12, 1518].
- 4,5- , , [12, 14, 15, 17],
CO [12, 14, 17]
[RCOC(R')=C=O]+.
5--4-- 15
370405 (lg = 2.693.80), 520 [14].
13 4,5- (5), (2) (3) [4, 11, 12, 18] (. 2).
366

InterBioScreen

113.6 (c)

177.0 (c)

Ph

153.6 (c)

N
Ph

173.9 (t)

. 2. 13 4-[-(-)]-5--

3. 4,5- 2,3--2,3-
4,5- , ,
. ,
(20). 80 4,5- , [2].

. , , , ,
4,5- .
3.1
(2) (5) , , ,
.
3.1.1
5-(-)-4-- 8 , 5,5-3--2,4- 23 [11],
P2O5. 24 ( 13).
13
Bu- t

O
t -Bu

H2O
P2O5

O
O
8

OH

t-Bu

t-Bu

O
H2O

t-Bu

O
23

, 2

t-Bu

24

367

[3,4][2,1-b]-2,3- 3 25 [5],
( 14).
14
H2O

H2O,

OH

25

4--5-- 7
(1)(2) (3)(4) [21] ( 15).
C 15

Ph

R = H, Alk

O
O

ROH

Ph

Ph

Ph

O
RO

O
OR

4--5-- 26
3- 27 [22], ( 16).
16
Alk

Ar

Alk'OH

O
O
26

O
OAlk'

Ar
Alk O
27

3.1.2
-, - 4,5-- 28
29 30 [79, 23]
( 17).
368

InterBioScreen

17

O
R = Ar"

H
N

Ar'

Ar

Ar

Ar'

O
O

Ar"

29

RNH2

R = Alk, Het

28

R
N

OH
Ar'

HO

Ar
30

4--5-- 7 - 31 1 : 2, -
C(5) 32 [24, 25] ( 18).
18
NO2

O
HO
O

Ph

H
2 ArNH2
N
Ar
Ph
N
Ar

Ph

Ph

Ph

H
N
Ph O

NH2

OH
O

31

O2N

32

[1,2-b]2,3- 3, 1--2- 33 [5]


( 19).
19
R

H
N

R'

O
O

O
O
3

R = H, Me; R' = Me, Ph

N R'
R

33

, 2

369

5--4-- 19 20
2--3-[()] 34, 5--1--4--2,3--2,3- 35;
[61] ( 20).
20
R

H
N

Ar

Ar'

Ar'
N

N
Ar

NH2

O
N

Ar

19

34

Ar

Ar
O

AcOH
H2O

Ar

35

3.1.3
5 4--5-- 7
36 [26] ( 21).
21

Ph

Ph

O
O

OH
R'

O
7

H
O

O
Ph Ph O N
36

R'

3.2
4,5-
.
370

InterBioScreen

3.2.1
4,5-- 28
3,4--2,4-
5,6--4,6--1,2,3,6--3- 37 [7, 9],

38. 4,5-- 1,2-
39 [7, 9] ( 22).
22

OH

Ar
Ar'

RNHNH2

R = H, Ar"

O
O

Ar'

Ar
HO

N
R

28

NH

Ar'

, AcOH
R = COAr"

O
N
R

Ar

NH

38

37

Ph
Ph

O
O

H
N

Ph
N
H

O
N

Ph

39

4--5- 7 40;
5--2,6--4--3- 41 [27] ( 23).
23
Ph

OH
O PhNHNH
2

O
Ph

Ph

O
Ph

Ph

PhNHNH2
PhNHN=CRR'

HO

Ph
N N

O
41

Ph

Ph
7

40

[1,2-b]-2,3- 3
42 [5] ( 24).
, 2

371

24
NH2NH2

H
N

H
N

O O

O
42

3.2.2
- , 4--5- 7 43 [28, 29] ( 25).
25

H2N

NH
R

Ph

Ph

O HO
Ph

N
N
H

Ph

OH
R
X

Ph
H2O
CO2

N
Ph

R
X

43

7
R = H, NH2; X = O, S

3.2.3 1,2-
4--5-- 7 - 3-()-1,2--2- 44, 45 [30]
( 26).
26
Ph

H2N

Ph

NH2

H
N

O
H2O

O
O

372

44

Ph

N
O

H2O

O
Ph

Ph

Ph

45

InterBioScreen

5--4-- 19 -, N-- 1,2- 4648 ( 27).


27
NH2

HN

Ph

NH

46 O

NH2

Ar
Ar

N
19

N
H

Ar

Ar

NH2

Ar

N
O

Ar
Ph

HN

H
Ph N

47

Ph

N Ph
H

N
O
Ph

Ph
Ph

48

2,3-(2--4,5--4,5--3-) 22
- 2,3-[-(3--3,4--2-)Z-]-1,2,3,4- 49 ( 28).
28
O

Ph
Ph

O
O

22

NH2

NH2
H2O

H
N
N
H

Ph O

H
N
N
N

Ph O
49

, 2

N
H
373

4--5-- 7 1,2- 50 2-[2,3-b][1,2-b]-as-


51 [31] ( 29).
29
N

NH2 ClO4
NH2
N
+

Ph
Ph

N
N

50

H2O

O
O
7

ClO4

51

PhCO2H

H2O

Ph
O

Ph
N

HClO4

Ph
N

O
Ph

3.2.4
5--4-- 19 (Ar = Ph) (2) (5)
( 30).
30
Ph

O
N

NH2NHR

O
Ph

Ph

Ph

R
HN
NH
O

19

N
N
Ph
HO

Ph

OH
O
N
R

NH

3.2.5
5--4-- 19 -
(2) 3--2-(1--3--2---4,5--3-) 52 [62] ( 31).
374

InterBioScreen

31
N

Ar

N Ar'

O
O

N
Ar

Ar

Ar

N
O

19

Ar'

N
52

3.3
1,3- (5)=(4)C=O 4--5-- 7 .
.
3.3.1
[3,4-b]-2,3- 53 [32, 33] ( 32).
32

O
Ph

O
O
O

Ph

N Ar

Ph

Ph
Ph

N
Ar

Ph

Ar
7

N
53

3.3.2
4--5-- 7
[2,3-d] 54 55 [13, 20, 21, 32,
34, 42] ( 33).
, 2

375

33
O

Ph

O
O

2RNCO

Ph

N
O

N R
Ph
N R

3RNCO

Ph

Ph

O
R

Ph

N
R

55

O
54

3.3.3
4--5-- 7 - - 56, 55 [17,
20] ( 34).
34

Ar
N

Ph
Ph RN

NAr

Ph
Ph

Ph

O
O

Ph

O
O

56

Ar

55

[2,3-d]-2,3- 57 [17] ( 35).


35

Ph

Ph
Ph

[4+2]

O
N

Ph

MeNCO

Ph

O
Ph

Ph
Ph

O
O

Ph

N
O

[4+2]

O
N

Ph

57

376

InterBioScreen

-
[2,3-d]-2,3- 58 55
[17, 18, 20, 35] ( 36).
36

Ph

Ph
Ph

RN

NR

O
7

O
O
N
Ph
R

N
R

Ph

Ph

O
RNCO

NR

Ph
N
O

R
55

58

R = Et, i-Pr

Ph

O
O
N
Ph
R

N
R

Ph

RN

R
N

3.3.4
4--5-- 7 4--5--2,3--2,3- 55 [18, 20] ( 37).
37

Ph

Ph
Ph RN S O

O
O

O 7
RN

Ph

O
O
N
Ph
R

Ph
Ph

O
SO2

O
O

Ph
O

N
Ph
R

S NR

O
N
R

O
S

R
N

RNSO

N
R

Ph

Ph
O

O
N
Ph R

, 2

377

Ph

Ph
N
O

R
55

R = t-Bu, Ph, Ts

3.3.5
N- 4--5-- 7 [4+2]- [3,2-c]-2,3,6 59 [16, 35, 39, 40] ( 38).
38
Ph
O
R'

Ph
R

R'

O
O
N
Ph
R'

R
Ph

Ph

O
R

Ph

59

O
O

Ph

O
R'

R
O

Ph

Ph

R
O

O
O
N
Ph
R'

3.3.6
4--5-- 7 N-(4-) [4+2]- [3,2-c]-2,3,6- 59 [35]. 3--2,3-2- 60 [2+2]- [35, 36] ( 39).
378

InterBioScreen

39
X
Ph

Ph

Ph

Ph

Ph

Ph

Ph

Ph

Ph

O
O

X=C=O

Ph

O
60

Ph

Ph

O
O

Ph

Ph

Ph

O
Ph

O
Ph

Ph

59

4-[-()]-5-- 61 1,3- [3,2-c]-1,3,6-


59 [16, 20] ( 40).
40

Ar
N

Ph

Ph

Ph

Ph
Ar

Ph

[4+2]

O
Ph

O
O

Ph

Ph

59

61

3.3.7
4--5-- 7 1-4--5--2,3--2,3- [37].
[38],
N--2,3- 55 ( 41).

Ph

41
R

Ph

Ph Ph

O
O
O 7

Ph

Ph

R
O

O
N
Ph
R

Ph

O
O

Ph

, 2

379

R
N

Ph

Ph

Ph

O
PhCHO

Ph

55

R = Alk, Ar

4--5-- 7 N,N'--- --2,3- [38].


3.4
(LR) 2,4--(4-)-1,3,2,4--2,4 4-- 4--5-- - 62, [41]
( 42).
42
Ph
O

R
Ph

O
O

LR

O
Ph

O
O S

R
S

O
O

S2

O
Ph

R
Ph

O O
O

O
O O
62

Ph
R

R = Ph, CO2Et

3.5
4--5-- 7 4--2,3--5--1- 63 [42]
( 43).
380

InterBioScreen

43

O
Ph Ph3P=CH2

Ph

P+

R
HO

Ph

O Ph

Ph

HO
Ph

Ph

Ph

R
Ph
Ph
Ph

Ph

P+
O
Ph

R
O

Ph
Ph

Ph

P+
O
Ph

63

5--4-- 15 4- Z-2-5--4--2,3--3- 64 [51, 52] ( 44).


44

Hal

Hal
Ar

O
O
O
15

Ph3P=CHCO2Alk
Ph3P=O

Ar

O
O

O
64

OAlk

3.6
5--4-- 2 (-) 65, 66 67 [19]
( 45).
, 2

381

45
O

Ar

N2

H
O

MeCHN2

Ar

N2

(2)O(1)

CH2N2

N2

(2)=O

O
2

Ar

O
O

O
65

Ph2N2

MeCHN2


(3)=O

O
OEt
Ar

Ar
O

O
67

66

4. 2,3--2,3-
, (130140). 5070. ,
( CO) 68 [6, 14, 4346] ( 46).
46

R
R'

O
O
O

R
R'

O
68

- , 4--5-- 1 [47],
2140 1, 196 [47]. 79 , .

5--4-- 15 , ,
. , 382

InterBioScreen

[2s+2s+2s],
4- [14].
(), ,
[4+2]- [53], - .
4.1
, 4,5-
, .
[4+2]-,

==, = .
69, 4,5-[2,1-b] 70,
71 [6, 49] ( 47).
47

[4+2]

CO2

O
69

70

71

, 2- 72 ()-
(), [6, 44, 45,
48] ( 48).
48

R
Ar

O
O
O

CO2

O R

R
Ar

O
Ar

[4+2]

R
Ar

O
Ar
R

72

R = Ar', Me

3,5--6--3--2,4- 73 (Hal = Br),


() 74, , [14], 6- , 2

383

3--5--4--2- 75. 73 (Hal = Cl),


, 5-(-)-4-- 76 (Ar = p-Tol, Hal = Cl) [14]
( 49).
49

Hal
Ar

CO2

O
76

Hal

Hal

[4+2]

Ar

O O

Ar

O
74

Ar
Hal
O

73

OH

Hal

Ar
O

Ar

75

4--5-- 7 CO
[44], [4+2]-. 77 CO2 1,3- [1, 47, 49, 50]
( 50).
50
O

Ph

Ph
O
O

CO2

[4+2]

O
Ph

Ph

Ph

Ph

COPh
COPh
O

77

O
Ph

Ph
CO2

Ph

Ph
O

[1,3]PhCO

384

Ph
O

Ph

Ph
Ph

InterBioScreen

[4+2]-
= , 78 .
79 [44, 49, 50] ( 51).
51
O
[4+2]

O
O

R
O
O

R
R
O

78

O
R

[4+2]

O
O

R
R

R
O

79

R = t-Bu

4-[-()]-5-- 61
() 80, 4- 81 [17]
( 52).
52

R
R

Ph

O
Ph

O
O
O

Ph

CO2

61

Ph

Ph
O

Ph

80

N
H
81

5--4-- 19 5--2(3--2-)-4--3--1-[1,2-a]-1-
82 [63] ( 53).
, 2

385

53

O
O

Ar

Ar

Ar

[4+2]

N
N

CO2

Ar

Ar

Ar

O
Ar
N

O
COAr

19

Ar

N
[1,3]COAr

O
Ar
Ar

N
O
Ar

O
O

N
N

82

4.2 C=O-, C=S-, CN-


, 5-(-)-4-- 8, [4+2]-, 83 [49] ( 54).
54

R
O

CO2

O
8

386

R = t-Bu

O
R

O
S

R
R

O
83

InterBioScreen

4--5-- 7 120 , , 1,3--4- 84,


170 , 3,5-2,6--4- 85 [54] ( 55).
55

Ph
Ph

120C

CO2

Ph

O
7

CO2

Ph

170C,

R'

O
Ph

Ph

O
R

Ph

85

O
R

Ph

R'

Ph
O

Ph

84

R
R'

4,5-- 28 () 86, [4+2]-


87, 88
[55, 56] ( 56).
56
O=C

O
Ar
Ar'

Ar
Ar'

CO2

O
O

Ar

28

(CH2)n

Ar'
86

O
(CH2)n

O
87

O
Ar
Ar'

O
O
88

, 2

387

5--4-- 19 138140
3--2-(6-4--2- 4-1,3--5-) 89 ( 57).
57
O

Ar

, R

CO2

Ar

Ar
O

Ar

R'

R'
O

O
R

19

Ar

Ar

O
O

89

R
R'

[4+2]- (),
, , ()
== ,
; .
, 4--5-- 7, 2--5--6--1,3--4- 90 ( 58).
58
O

Ph

Ph
O
O
7

CO2

O
Ph

Ph

O
N

Alk Ph

Ph

Alk

90

, 90,
9--8--6-[2,3-c]-6,10- 91 [57] ( 59).
388

InterBioScreen

59

Ph

Ph

Ph

Ph

O
O

N
H

91

4.3
92 [58]
( 60).
60
O

Ph
Ph

CO

O
Ph

RN

Ph
Ph

Ph

R
O

92

, [4+2]-,
- , 93
[44, 58] ( 61).
61
R'
R

R'

O
CO2

O
O

N
R"

N
R"'

R'
R

N
O

R"
N
R'"

93

5--4-- 19
[4+2]-
94, 95.
.
= C=N ,
96 97 [44] ( 62).
, 2

389

62

Ar

Ar
O

CO2

N
Ar

Ar

19
p-RC6H4CH=NC6H4R'-p

Ar

H11C6N

Ar

Ar

Ar

O
O

NC6H11

O
O

94

R'

95

X=O

R
R

O
O

CO2

O Ph
R

N
R

R = t-Bu

Ph
Ph

96

Ph

X = NTol-p
8

Tol-p
Ph

O
97

Ph

4,5-[1,2-b]-2,3- 98
99
[49, 60]. , 1--2- 100 [60]
( 63).
390

InterBioScreen

63

RNSO

O
O
O

99

CO2

N
S
N

98

SO

OH O

O
NH
R

H2O

S
O

S
N

O
N
H
NH
R

100

4.4
, 4,5-
, , .
, 5-(-)-4-- 8,
101 [50]
( 64).
64

R
R

O
O
O

CO2

O
R

MeOH

OMe

O
R

R = t-Bu

, 2

R
101

391

4--5-- 7
102, 103 [27, 28] ( 65).
65
N

OH

Ph

Ph

O
O

Ph

Ph

CO2

O
O

Ph
O

O
Ph

Ph

N
R

N
O

Ph

102

Ph
NH

Ph
N

Ph

O
Ph

Ph
N
O

Ph
103

4.5
5--4-- 15 9-
, ,
2- 104, 105 [46, 59]
( 66).
66
Br
Ph2CN2

Ar

Br

Ar

104

O
15

Ph
Ph

N2

Br

O
O

Ar
105

392

InterBioScreen

5--4-- 2
, -,
[45].
5.
4,5- 2,3--2,3-
, , , [1, 3, 418, 22], . , ,
[912, 14, 2325, 2760, 64].
, , [20, 27, 28,
35, 41, 50].
( 01-03-32641, 02-03-96411).

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.

Ziegler E., Eder M., Belegratis C., Prewedourakis E., Monatsh. Chem. 1967
98 2249.
a) .., ..; b) ., .
2,3-, . .., : - .
-, 1994.
.., .., . . 777 030, . . 1980
(41) 88.
.., .., 2002 38 (10) 1544.
Horton W.I., Hummel C.E., Jonson H.W., J. Am. Chem. Soc. 1953 75 (4) 944.
Murai S., Hasegawa K., Sonoda N., Angew. Chem. 1975 87 (18) 668.
.., .., .., 1992 28 (6) 1287.
.., .., . . . .
": ", , 1990, . 107.
.., .., . . . ,
, 1991, . 12.
.., .., .. ., 2000 (4) 556.
Kollenz G., Kappe C.O., Abd El-Nabi H.A., Heterocycles 1991 32 (4) 669.
Saalfrank R.W., Lutz T., Hoerner B., et al., Chem. Ber. 1991 124 (10) 2289.
Kollenz G., Penn G., Dolenz G., et al., Chem. Ber. 1984 117 1299.
.., .., .., 1984 20 (8) 1749.
Alper H., Vasapollo G., Tetrahedron Lett. 1989 30 (20) 2617.
Kollenz G., Penn G., Ott W., Peters K., et al., Heterocycles 1987 26 (3) 625.
Kollenz G., Penn G., Ott W., Peters K., et al., Chem. Ber. 1984 117 (4) 1310.
Heilmaeyer W., Kappe C.O., Sterk H., et al., Chem. Ber. 1993 126 2061.
.., .., .., .., 1998 34
(1) 112.

, 2

393

20. Kollenz G., Heilmaeyer W., Sterk H., Synthesis and applications of isotopically
labelled compounds, 1994, . 773.
21. Kollenz G., Ziegler E., Ott W., Igel H., Z. Naturforsch. B 1976 31 (11) 1511.
22. Kozlov A.P., Konovalov A.Yu., Maslivets A.N., Andreichikov Yu.S., 5
International Symposium on Furan Chemistry, 1988, . 134.
23. .., .., .. ., . . 7 .
. " ", 1991, . 129.
24. Penn G., Thesis University of Graz, 1984, . 52.
25. Terpetschnig E., Diploma Thesis University of Graz, 1984, . 40.
26. Akcamur Yu., Kollenz G., Orp. Prep. Proc. Int. 1987 19 (1) 52.
27. Akcamur Yu., Penn G., Ziegler E., et al., Monatsh. Chem. 1986 117 (2) 231.
28. Akcamur Yu., Altural B., Saripinar E., et al., J. Heterocycl. Chem. 1988 25
(5) 1419.
29. Altural B., Akcamur Yu., Saripinar E., et al., Monatsh. Chem. 1989 120 1015.
30. Ott W., Ziegler E., Kollenz G., Synthesis 1976 (7) 477.
31. Juhasz-Riede Zs., Hajos G., Kollenz G., Messmer A., Chem. Ber. 1989 112
(10) 1935.
32. Kollenz G., Akcamur Yu., Istanbul Ueniv. Fen. Fak. Mec. Seri C 1981 46 75.
33. Kollenz G., Ott W., Ziegler E., et al., Liebigs Ann. Chem. 1984 (6) 1137.
34. Peters K., Kollenz G., Chem. Ber. 1981 114 (13) 1206.
35. Terpetschnig E., Penn G., Kollenz G., et al., Tetrahedron 1991 47 (19) 3045.
36. Penn G., Kollenz G., Oesterr. Chem. Z. 1983 234.
37. Ott W., Terpetschnig E., Sterk H., Kollenz G., Synthesis 1987 (2) 76.
38. Ott W., Kollenz G., Ziegler E., Synthesis 1975 (7) 433.
39. Fabian W., Kollenz G., J. Mol. Struct. (Theochem.) 1989 187 199.
40. Fabian W., Kollenz G., J. Org. Chem. 1997 62 8497.
41. Kollenz G., Penn G., Theuer R., et al., Tetrahedron 1996 52 (15) 5427.
42. Kollenz G., Ziegler E., Igel H., Labes Ch., Chem. Ber. 1976 109 (7) 2503.
43. Andreichikov Yu., Shurov S., Maslivets A., Int. Chem. ongress of Pacific Basin
Societies, 1995, p. 1137.
44. Kappe C.O., Faerber G., Wentrup C., Kollenz G., J. Org. Chem. 1992 57 7078.
45. .., .., .., .., 1997 67
(4) 674.
46. .., .., .., ..,
. . " ",
1988, . 27.
47. Wentrup C., Winter H.W., Cross G., et al., Angew. Chem. 1984 94 (10) 791.
48. .., .., .., 1980 26 (11) 2336.
49. Wentrup C., Heylmayer W., Kollenz G., Synthesis 1994 1219.
50. Kappe O.C., Evans R.A., Kennrad C.H., Wentrup C., J. Am. Chem. Soc. 1991
113 4234.
51. .., .., .., 1985 21 (2) 402.
52. .., .., .., 1989 (8) 1034.
53. Jaeger G., Wenzelburger J., Liebigs Ann. Chem. 1976 1698.
54. Kollenz G., Ziegler E., Ott W., Kriwetz G., Z. Naturforsch. B 1977 32 (6) 701.
55. .., .., . . "
", , 2000, . 40.
394

InterBioScreen

56. .., .., . . "1-


.. ", , 2000, . 140.
57. Ziegler E., Kollenz G., Kriwetz G., Ott W., Liebigs Ann. Chem. 1977 (10) 1751.
58. Kollenz G., Igel H., Ziegler E., Monatsh. Chem. 1972 103 (2) 450.
59. .., .., 1984 20 (2) 411.
60. Minami T., Yamauchi Y., Ohschiro Y., et al., J. Chem. Soc. Perkin Trans. 1 1997
(8) 904.
61. .., .., .. ., 2002 (3) 398.
62. .., .., .., .., 2001
(9) 1282.
63. .., .., .. ., 2001 (10) 1429.
64. .., 2001 (3) 291.

, 2

395

-4,5-
..

614600, , . , 15

, -4,5-
, 1914 . [1], 50-
. ,
(,
-2,3- -2,3-)
[2].

. -4,5-,
-4,5-, [3]
.

-4,5-
-4,5-
. ,
-4,5- 1 [4, 5] ( 1).
1

R'

Cl

Cl

R'
N

O
1

R = Ar; R' = Me, Bn

N-()
-4,5- 2.
2 N-(), N--- [6] ( 2).
396

InterBioScreen

2
R

O
R'

O
R

N
H

Cl

OH

Cl

R'

O
O

R = Me, Vin, Ar, Bn; R' = H, CHal3


2--4,5- 35 ( 3).
3
O
Cl

N
H

Cl

Ph

Ph
N
O

[7]

3
O

Cl

Cl

Ph

Ph

H
N

NH2

[7, 9]

4
O
Ph

N
H

[7, 8, 11, 12]

Ph

O
O
R

O
O

5
R = OH, OMe, Cl, NHPh


2--4,5- 6; ,
[7, 10] ( 4).
4
O

R'

Cl

+
O

Cl

H
N

R'
R"

O
R, R', R" = H, Et, Cl, Ar

R"
N

O
6

, 2

397

.
, N--N'- -4,5- 7 [13]. HCl
( 5).
5

O
O

Cl

+
O

H
N

F 3C
O

Cl

H
N
O

O
S

Ar

Ar

CF3
N

-4,5- 8 2,3--4-1,4- [14] ( 6).


6
O
O

O
S

R''

N
R'

R'
N

R''

O
O

O
R

R = OEt, Ar; R' = Me, Ph; R" = Ph,

O
O

O
O

- --,- -4,5 9 [15] ( 7).


7
R'

R
NH2

X
R'

SH

O
Et

R"
Cl

NaH
KOH

R = H, Cl; R' = H, OMe; R" = Alk; X = CH, N

X
N

N
S
R"

O
O

-4,5- 10
[16] ( 8).
398

InterBioScreen

8
O

HN

R'''

R''

O
O

Cl

Cl

R''

CH2Cl2

R'

Cl

R'''

R'''

R'

O
O

FeCl3

R
R''
R'

10

R, R', R'' = H, Alk, OAlk; R'" = H, Ar, OAc

11 [17] ( 9).
9

R
R

R R

H
N
H

N
O

Cl

Cl

FeCl3

CH2Cl2

O
O

11

R = Me; R+R = (CH2)4, (CH2)5; X = Cl, CF3


---4,5- 12 [18] ( 10).
10
O
O
(CH2O)n

+
O

NH2

H2SO4

NH2

O
N

O
12

O
O

-4,5-
2,3-
4 .
,
.
, 2

399

5
13 [7, 10, 11] (., , 11).
11
O
Ph

O
Ph

N
H
O

H2O/HO

N
H
O

Ph

O
Ph

O
13

5
14 [7, 8, 10] ( 12).
12

O
OMe

Ph

O O

Ph
EtOH

O
O

OMe
N

EtO

O
14

10 .
15 [16] ( 13).
13
R'''

O
O

MeOH/H2SO4
19 : 1

R''

R'''

R'

R''
R'

R
10

15

16 ,
17 18 [17]. ,
( 14).
400

InterBioScreen

14
O
N
16

N
H

MeOH/H2SO4
19 : 1

+
N

MeO

17

18

() 12 .
(NH)2CH2, BuNH2 ---- [18].
19 (2)-,
(3)-N. 20 [19] ( 15).
15

Cl

R
Cl

O
R'

H
N

NH
Cl

R''

Cl

N
R'

R''

S
R

19

R'
O

HCl

Cl

R''

O
R

20

9 80100 21. 22.


23
[20] ( 16).
, 2

401

16
R'

X
N

AcONH4

N
S

N
R" H

21

NH2
R'

X
N

O
O

N
S
R"

NH3

AcOH

O
R"
OH

Cl

S
22

O
R
R"'NH2

O
NH

X
R'

R"'

N
H

S
R"

23

9

(2)- N(10)-C(3a), N-(-3)- N-(-5) 24.
HCl 25 [21, 22] ( 17).
17

O
N

X
R'

R
O
R"

S
9

O
NH2NH2

R'

O
NH

X
N

O
N
H

R
HCl

S
24

NH2

R"

R'

O
N

X
N

NH
NH
R"

S
25

19 PCl5 POCl3 100105


4
, 26
[23] ( 18).
402

InterBioScreen

18
O

POCl3, PCl5

Cl

Cl

R
Cl

26

19

. , 1 90110
[5] ( 19).
19
R'
N

t
CO, CO2

R'

2--4,5- 6
190200 27
[7] ( 20).
20

Ph

H
N

190200C

NCO

Ph
27

R = H, Ph

11 150175 28 [17] ( 21).


21

O
N

O
O

Cl

t
CO, CO2

11

Cl

N
28

, 2

403

. 1 11
[5] [16, 17], .
9 [15, 24].
( 01-03-32641,
02-03-96411).

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.

404

Feist F., Ber. Dtsch. Chem. Ges. 1914 47 1173.


2,3-, . ..,
, 1994, . 147, . 166.
.., . ,
. .., .., .: -, 2001, . 2, . 217.
.., .., .., . . 819 100,
. . 1981 (13).
.., .., .., 1982 (8) 1126.
Bohme H., Ahrens K.H., Tippmann E., Arch. Pharm. 1977 310 (3) 242.
Speziale A.I., Smith L.R., J. Org. Chem. 1963 28 (7) 1805.
Spielman M.A., The Chemistry of Penicillin, Princeton, 1949, . 239.
Skinner G.S., Miller C.B., J. Am. Chem. Soc. 1953 75 977.
Skinner G.S., Ludwig R.E., J. Am. Chem. Soc. 1956 78 4656.
Cheehan I.C., Corey E.I., J. Am. Chem. Soc. 1952 74 360.
Cheehan I.C., Buble E.L., Corey E.I., et al., J. Am. Chem. Soc. 1950 72 3828.
.., . . . .
, , 1989, . 1, . 68.
Toda I., Seki M., Amano K., et al., Chem. Pharm. Bull. 1994 42 (3) 739.
.., .., .., .., 1979
(2) 250.
Larsen R.D., Reamer R.A., Corley E.G., et al., J. Org. Chem. 1991 56 (21) 6034.
Bernotas R.C., Adams G., Nieduzak T.R., Synth. Commun. 1996 26 (18) 3471.
Gilbert E.E., J. Heterocycl. Chem. 1971 8 (2) 327.
.., .., .. ., 1993 (8) 1125.
.., .., .., .., 1986
(7) 992.
.., .., .., .., . .
638 068, . . 1979 (43) 259.
.., .., .., .., 1993
(4) 559.
.., .., .. ., 1984 (9) 1191.
.., .., .., .., .
, . .., .., .:
-, 2001, . 2, . 139.

InterBioScreen

- ,
,-

.., .., ..
. .. ( )
119991, , , 47
,
[18]. - ,
[4, 5]. -
[6, 7].
,
, .
, ,
N- 2-() 5 [9].
4--2- 4--3--2- [10]. ,
-
, -
, . [11], ,
, .
,
.
- , , ,-
, .
1. 2--1,3-
2--1,3- .


, . ,
, , , 1 (. [12, 13]). , 2
1 ( 1).
, 2

405

OH O

H
N

H2NNH2

H
O2N

NO2

1 3,
4 [14, 15] ( 2).
2
OH O
H

NC

CN

O2N

S
NH2

NO2

N
H

NH2

O
Ar

Br

O2N

O
Ar

3-
1--4- [16, 17], 3- 5
6 [18] ( 3).
3
NO2
H 2N

Cu/2
5

NH2

N
O2 N

Cu
N

NO2

7 1,3- 8 3--2-(1H)- 9 [19] ( 4).


406

InterBioScreen

4
OH

O
O

EtO

OEt

NH2 O

NO2

R
R

N
H

NO2
7

R = Me, OMe

7 10
[20], 2- 11 6- [1,2-a] 12 [21] ( 5).
5

S
H2N

NH2

O 2N
HO

EtO

NH2

OEt
NO2

N
H

10

NH
11

NH

H
N

N
N

O2N

OH
12

2.
-
.
, .
2.1 ,

. ,
13 14
, 2

407

- , , - . 14
, 1,3-, , 1,2,4- [2224]. 14 15,
, , , 16,
N- 17. 18,
19, N- [25] ( 6).

EtO
NO2

EtO

H2O

OEt

14

13

EtO2C
N

N O
O
15

CO2Et

O N O

EtO

OEt
R

NCCO2Et

N O
O

17

16

OEt

O N O
18

R
R

OEt

+
O

19


. 20

2,4- 21, , , N- 22 [26]
( 7).
408

InterBioScreen

7
O

OR' R"

R'O
NO2

R"

OR'

R"

N O
O

R'O

21

20

NO2 NO2

OR'

22

2- , 20 . -
.
N- , [27, 28].
23 24 [29] ( 8).
8
R' = Alk, R" = H

NO2

N
R"

23

26

O
H

N
R'
27

MeO

O2N

N
R'
24

R'

R' = R" = Alk

MeO2C

CO2Me

N O
O
28

N O
MeO2C

CO2Me

R'

CO2Me
O N
25

24 23,
25.
26 24
, 2

409

.
27, 28.
[30], 20 22 -
4 5. 22
5.
13 29
-N- 31 - [31].
, -, 30
31. , -, 30 ( 9).
9

EtO

29

13

OH

O2N
O

NO2

OH

OEt

OH

O
+
N
O

OEt
O

30

31

13 ,- 32 33, S,S-
34 [32] ( 10).
10
R'

EtO

NO2
32

13

SO2
H 2N

R'

O
Ar

NH2

Et3N, i-PrOH

O
O2 N
33

Ar
O
H2N

O
OEt
O

R'

H
N

EtO
O

OEt

410

Ar

R'

Ar
34

InterBioScreen

13
. , 35 [33]
36,
35 37 [34] ( 11).
11
O
EtO

OH

NO2

NO2

13

N
R

O
O
N
R
35

36

O
NO2

MeNO2, K2CO3

(R = H)

NH2
37

13 2- 3--2--1,8 [35]. 13 - 38 KOH 39 [36], 13 40


41 [37] ( 12).
12
NH2
SH

38
KOH, EtOH

O N+ N

EtO

N
OH

39

NO2
13

H
N

40

O
N+

N
OH

O
OEt

41

, 2

411

42
. 43 42
44, 45, 46 42
47. 45 47
-
[38, 39] ( 13).
13

NH2
O2N
NC
42

+
R

N N

N N

N2Cl

N
H

H
N
N

N
H

44

43

CN

NO2

N N

N
NO2

45

NH2
CN

N N
N N
H

NO2
42

NO2

N2Cl

N3

47

46

42
3- 5--4- [40].
42 - 48 49 [41] ( 14).
14
O

CN

NO2

SH

42

H2 N
O2 N

48

49

[42] , - 38 42 , , - 2-() 50
( 15).
15

CN

NO2
42

412

38

NH2

SH

S
50

NO2
+

NH4

InterBioScreen

, ,
.
, , 3-. , 51

4,6--3--2(1H)- [43]. 53,
52 51,
54, ,
55 [44] ( 16).
16

OH

R"

R"

H 2N

NO2

R'

R'

52

51

N
H

NO2

R"

R'

53

NH2
N
H

54

O
NH

+ CH2O

R"
O

H
N

R'
N
H

N
O
O
55

N- 56 57 [45] ( 17).
17
R

O
O2N

HO N
CF3SO3H

N
H
56

O
N
H
57

2.2 -
-. [40], 58
, 2

413

59 60
( 18).
18

O
R

OH

Cl

R'

NO2
58

R
O2 N

N
R'

60

59

58 61 63.
62 [46]. 58
64 [47] ( 19).
19
R'

R
NO2

61

O N

N O

H2O

58

R'

R
62

R'

63

OAc
64

- - - 65. ,
65
2--3- 66 (R'' = Me) [48].
58 - 2--3- 66 (R'' = Ar) [49] ( 20).
20
R'
O

NO2

R"
NO2

NH2
65

R'

58

R"

66

,
2- 3- 66 (R'' = H) [50].
414

InterBioScreen

- 58 (R'' = Ph) - 38
KOH 67, 39
( 21).
21
O

SH

Ph

N
OH

Ph
NO2

NH2
38

67

58

, - ( 12, 15, 21),


, [36, 42].
- 68
2- 69 [51] ( 22).
22
NH2

Na2S2O4, NaOH

Ph
NO2

NH2
68

58

Ph

69

70 71 3- 72 [52] ( 23).
23

OH

HO

O
HO
HO
70

OH

HO

NH

HO

NH2

NO2
71

HO
O2N
72

, - 74 [53] . , --- 73 74 75,


, 2

415

- 58 (R = Ph) ( 24).
24
O

Ar
NO2

OH
NO2

NC

CN

CN

74

73

CN

Ar

O
O
O

NH2
CN

O2N

Ar

75

76 71
77,
78 [54],
( 25).
25

O
O

N3

H
N
N3

NO2
71

NO2

X
O2N

76

77

78

X = O, S, Se

--- 79
. 80,
[55]. - 79
81 [56] ( 26).
416

InterBioScreen

26

R'

Py

NOH

R"
NO2

R'

R"'
80

R"

OH

R"'

R'

79

NO2

R"

O
R"'
81

2,2'- 82 83 [57], , ( 27).


27
Ph
NO2
O

NH
N

NO2

+
PhN2X

O
NO2

NO2

NO2
83

82

N
Ph

71,
, [58]. , 71, 84 85 86 ( 28).
28
H
O

F
84

OR

+
NO2

O
O2N

O
OR

NH2
N
H

F
71

85

, 2

86

417

-
[4,5-d],
[59]. 87 88,
89 90,
91. ,
92 93 [4,5-d] 95 94 ( 29).
29

N
NH2OH

OH

Cl

OEt
89

NO2

88

O 2N

O
N
R

90

OEt

OEt
O

NO2

NO2

87

OEt

O
Zn

H2 N

HCl

91
MeC(OEt)3
94

NH3

O
N

H 2N

O
N
R

92

NH2

93

NH

O
O

R = 2,4-ClC6H3

95

3. ,-

-
, ,-
,
1,3- .
3.1 -- -
96 97 56 98 5060% [60]. 96
418

InterBioScreen

100 3--4- 99,


3-, 2, 4
[61, 62] ( 30).
30
Et
N N

Et
N
N

97

N
NO2
Ar

NO2

98
Tos

Ar
96

H
N

N C
100

t-BuOK

NO2

Ar
99

101 96 102
103 [63].
102 104
( 31).
31

NO2

O
HN
R*

Ar
96

O
R

HN
R*

101

OEt

OEt Ar

OEt

NO2

Ar

R
N
R*
103

102

OEt

O
R

Ar

N
104

, 2

419

96 105 106.
, 106 108 [64]. , ,
107
( 32).

32

R'

Ar'

+
S

Ar

Ar

Ar

AcOH

Ar'

R = H;

C6H6

O2N

NO2 R' = Ar"


R

96

105

Ar'

NO2H
NAr"

R'

107

106
AcOH
R = R' = Me

Ar

Ar'

Ar

Ar'

NO2

NO2
HN

109

108

Ar"

, 105 (R = R' = Me) 106,


, , 109. [65],
32 -- 106
(R = R' = Me).
110 113
, , [66].
111 =
110 112, ( 33).

MeO

N
110 R
420

NO2

MeO

SnBu3
N
111

Boc

33

NO2
N Boc

N
112 R
InterBioScreen

H
N

O
NH2NH2

H
N

HCl

N
R
113

114 ,- 96
115, [67] ( 34).
34

Ar

NaH/

+
O2N

Ar

NO2 Me SiCl
3

Et3N

OH

96

Ar

Ar
N

MgBr

BF3Et2O

H
N

HO

NO2
114
DCC

R
O N
NO2

N
O

H
Ar

Ar

O
R

OCNC6H4NCO
Et3N

O
N

O
R
115

3.2 --, -- -


,- ,
, 2

421

-, - - . ,
1,1-()-2- 116 2--1,1-
.
-, - 1,1-()2- 116 66 (R = SMe) [68, 69].
2--3-
116 [70].
117 1,1-()-2- 116
118 119 [71] ( 35).
35

R''

O2 N

R'" Et N
3

R'

X
116

R'"

R'

R'"

R'

R"

R"

CN

NO2

N
NC

117

N
NC

118

119

2--1,1- 120
121, 125 [72] ( 36).
36
O

O2 N
KS

SK

S
Br

NO2

121

120

SK

122

S
NO2

1--2--1- 123 -
124,
125 [73] ( 37).
37

KS

NH
Ph
123

422

O 2N

O2 N

R'

R
Br

Ph

S
O

N
H
R'

124

Ph

HN

O 2N

R'
R

125

InterBioScreen

1--1--2- 126 127 128 [74] ( 38).


38

O2N
S

NH
Ar

O2N

S
Cl

Cl

N
S

Ar
128

127

126

2-()-1,3- 129
130 131 [75, 76] ( 39).
39
O

S
H
N

NO2

S
129

130
O

OEt

NO2

O
N

OH

NO2
131

1,1-()-2- 116
132, 133 [77] ( 40).
40
O2N
S
116

NH2NH2H2O

O2N
H2NN

O2N
S

132

, 2

133

423

- 134, - - 1,1-()-2- 116


135 (X = O) 135 (X = NH). 136 [78] ( 41).
41
NO2

116

NH2

NO2

N
N

X = NH

XH

136

135

134
X = O, NH

137 1,1-()-2- 116


139.
N- 1--1--2- 138 [79] ( 42).
42
NH2
O

O2N
S

O
137

O
S

HN

O
138

116

O2N

O
NH

NO2
139

1,1-()-2- 116 140


141,
142, 143 [80] ( 43).
424

InterBioScreen

43
O2N
HO

O2N
S

H
N
O

NH2

NH3

t-BuOH

116

140

O
R
R'

N
R'
142

O 2N
H 2N

N
H

OH

R
N
NO2

141

N
H

OH

143

145 144 146 [81]


( 44).
44
O

O2N
HN

NH

O
H

OH
144

HN

145

NO2

N
H

146

, . , 1--2--1-
[82] 2--5--4-. 2--1--1- 1--5-4--1,2,3-,
[83].
, 2--2- 147
1,2,3- 148 [84]
( 45).
, 2

425

45

Ar

NaN3

NO2

Br

H
N

Ar

N
NO2

148

147

2--1,1,3,4,4- 149
, 3--4,5- 150 [85] ( 46).
46
Cl

Cl

Cl
Cl
O2N

Cl

Cl

Cl

Cl

Cl

Cl
150

149

,- 151 100
2- 152
[86] ( 47).

+
NO2
151

47

O
Tos

Tos

NH

N C
100

152

3.3 ,
-
,- 153 154 3035%.
, -,
- - .
[87] ( 48).
426

InterBioScreen

48

Ar
Na

NO2

O
NO2
Ar

NaCN
MeOH

NH2

N O

Ar

NC

153

154

- 155 . , 156 155 1,3- [88] ( 49).


49

Ar

Ar

NO2

+
O2N

CN

OH

155

NH2

156

13 157
2--3- 158,
. 158 ,
159 [89], 160 161 [90] ( 50).
50
O
HN
R

O
EtO

OEt

NO2
13

O2N

O2N
158

N
N
H

O
OEt

157

OEt

OEt

EtO

NH2

NH2
160

159

NH
R

O2N
O

R = Me, Ph

, 2

N
N
H

161

427

2- 162 2--3- 158


(2-) 163,
90 164 [91] ( 51).
51
OEt

O2N

R
N

OEt

NH2

N
O2N
O

162

158

H3PO4

NH

163

OEt

N
R

NO2
O

164

. , 165 158, 2-3- 166 3--2- 167 [92] ( 52).


52
X

Li

Ar

N
Si

OEt

165

O2N

NO2

X
Ar

OH

NO2

+
Ar

OEt

OEt
166

158
X = Ar, CONR2, CN

167

168 2--3- 158 169, MgHgCl2


170,
[93] ( 53).
53
O

OEt
O

O2N
158

428

NH

NO2

N
O

OEt
168

Mg/HgCL2

OEt

169

InterBioScreen

O
NH
N

O
OEt

170

171, , 2--3- 158


172 [94] ( 54).
54
O

OEt

OEt
O

O2N

OEt

OEt

O
171

158

NO2
O

172

158
: 1,2- 173,
158 1,1- 1,4- 174,
-, [95] ( 55).
55
R

H
N

N
H

R'

R' N

OEt

173

O2N

OEt
158

R
N

R'"
NH2
N
R"'
R"

O
NO2

R"
O

N
EtO

OEt

N
O
N
R"
R"'
174

, 2

429

176,
-
(-, ), 175 [96] ( 56).
56

OMe
MeO

OMe

R
NH

RNH2

XCH2NO2

175

NO2
176

R = Ar, Alk;
X = CO2Alk, COAlk, COAr, CN

177 (R = Alk, Ar)


178 [97] ( 57).
57

R'
NH
O

H2N

H
N

NO2

R"
N

R"

O2N

N
R

178

177

3,3-()-2- 179 177 180 [98100]


( 58).
58
NC
HN

NO2
NH

NH2NH2

H2N

H
N

O2N

179

N
N
H

180

181
182, -
430

InterBioScreen

183, 184
[101, 102]. 185 -,
182, 186, ( 59).
59

R
HN

O
Br

R'

HN
NO2
RNCS

HN

NH

Bn

HN

Bn

R
HN

Bn
BrCH2NO2

182

181

O2N

S
O2N

N
H
NMe2

Me2N

O2N

184 H

Bn

NMe2

Ph
Br

Ph

NO2

NMe2

Bn

N
H
183

NH

Bn

R'

O2 N

NO2

Ph
Ph

185

186

187, [103],
188 [104] ( 60).
60

O
NO2 [H]

R
R'
187

NH
Ar

NH2

R
R'

NH
Ar

R"C(OR"')3

R'

N
N
R"

Ar
188

R = Me, OMe; R', R" = H, Me; R+R' = CH2CMe2CH2

, 2

431

189 190
(R = CH3, H) [105] ( 61).
61

O
NC

NO2
HN
R

NO2

MeONa

N
R

H2N

NH
R

NH
R

190

189

,-
, 1-()-3,5--4(1H)-
191, 1,5--2,4--1,4--3-. 191 192 193 194 [106]
62 176.
62

O
O2N

O
NO2

NH2OHHCl

Py

N
R
191

NO2

Py

PyH

192
+

2PyH
NO2

NC

O
193

R'

R"
HCl

NC

NO2

R'

R"
194

191 ,
.

. R = CH3 191
195,
R = 2- 196 [107, 108]
( 63).
432

InterBioScreen

63

O
O2N

R = Me

O
O2N

NO2

N
R

OEt

195

OEt

N
R

OH
O2N

191

NO2

R =

OEt
196

191 1,3,5-
N- 3,5--4(1H)-,
1,3-, [108].

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.

- , . ., .: , 1972.
.., .., , : , 1995.
Barret A.G., Grabovsky G., Chem. Rev. 1986 86 751.
Rossini G., Ballini R., Synthesis 1988 (11) 832.
Shipchandler M.T., Synthesis 1979 (9) 666.
.., .., .., 1989 58 796.
Rajappa S., Tetrahedron 1981 37 1453.
.., 1994 (10) 1299.
Wieczorek J.S., Plazek E., Recl. Trav. Chim. Pays-Bas 1964 83 2449; Chem. Abstr.
1964 60 15822b.
Stadlbauer W., Fiola W., Fisher M., Hojes G., J. Heterocycl. Chem. 2000 37 1253.
.., .., , : , 1991.
Rajappa S., Nair M.D., Adv. Heteroycl. Chem. 1979 25 113.
.., .., .. ., 1998 34 1271.
.., .., .., .-. . 1997 31
(7) 18.

, 2

433

15. Peter F.M., US Patent 3 624 877; Chem. Abstr. 1972 77 88314d.
16. Eliseo Q.A., Alfonso S.A., Span. ES Patent 2 008 340; Chem. Abstr. 1989 114
164218.
17. Maria R., Span. ES Patent 2 008 770; Chem. Abstr. 1989 114 164220.
18. Fujiwara M., Kinoshita S., Wakita H., Chem. Lett. 1987 (7) 1323.
19. Dornow A., Plessen H., Chem. Ber. 1966 99 (2) 244.
20. Nutui R., Sebe I., Nutui M., Rev. Roum. Chim. 1974 19 679.
21. O'Brien D.E., Robins R., Simon L., US Patent 907 799; Chem. Abstr. 1976
84 4998.
22. (a) Shimuzu T., Huashi Y., Teramura K., Bull. Chem. Soc. Jpn. 1984 57 2531;
(b) Shimuzu T., Hironi H., Teramura K., Bull. Chem. Soc. Jpn. 1986 59 2827;
(c) Shimuzu T., Huashi Y., Teramura K., Bull. Chem. Soc. Jpn. 1985 58 2519.
23. Shimuzu T., Huashi Y., Hironi H., Teramura K., J. Org. Chem. 1983 48 3053.
24. Barlas J., Grook S., Leslie M.G., et al., Chem. Ind. (London) 1986 (16) 534.
25. Sagiyama T., Ohno A., Oka Sh., Susumi H., Kidorui 1988 12 112; Chem. Abstr.
1988 109 230867.
26. Dornow A., Wiehler G., Liebigs Ann. Chem. 1952 578 113.
27. .., .., 1970 (11) 1505.
28. Umezama S., Zen S., Bull. Chem. Soc. Jpn. 1960 33 1016.
29. .., . . . . 1974 (4) 845.
30. Melor J.-M., Texier-Boullett F., Foucand A., Synthesis 1988 (1) 55.
31. Rosini G., Galarini R., Maratta E., J. Org. Chem. 1990 55 781.
32. Quiclet-Sire B., Trevenot I., Zard S.Z., Tetrahedron Lett. 1995 36 9469.
33. Hadtmann G.E., Ger. Offen. Patent 2 635 216; Chem. Abstr. 1977 87 23245.
34. Gosteli I., Helv. Chim. Acta. 1977 60 1980.
35. (a) Haves E.M., Wibberley D.G., J. Chem. Soc. C 1966 315; (b) Haddadin M.J.,
Issidorides C.H., UK Patent 1 305 138; Chem. Abstr. 1973 78 136339.
36. .., .., 1961 31 531.
37. Haddadin M.J., Issidorides C.H., UK Patent 1 305 138; Chem. Abstr. 1973 78
136339.
38. .., .., .., 1984 (4) 557.
39. .., .., .., .., 1985 (5) 682.
40. Dal Piaz V., Pinzauti S., Lacrimini P., Synthesis 1975 (9) 664.
41. Jpn. Kokai Japan Patent 81 100 780; Chem. Abstr. 1978 96 19954.
42. .., .., 1962 32 3703.
43. .., .., .., .., . ,
. . 1997 (3) 559.
44. Hoffman J.M., Wai J.S., Thomas C.M., et al., J. Med. Chem. 1992 35 3784.
45. Kozikowsky A., Acc. Chem. Res. 1984 17 410.
46. .., .., .., .., 1998 34 2804.
47. Smith J., J. Org. Chem. 1972 37 2686.
48. Dornow A., Sassenberg W., Liebigs Ann. Chem. 1957 602 14.
49. Baumgarten H., Saylor J.L., J. Am. Chem. Soc. 1957 79 1502.
50. Ockenden D.W., Schofield K., J. Chem. Soc. 1953 (12) 3914.
51. Dornow A., Sassenberg W., Liebigs Ann. Chem. 1955 594 185.
52. Chiara J.L., Gomez-Sanchez A., Hidalgo F.J., Carbohydr. Res. 1989 188 55.
53. .., .., .., 1998 (12) 1661.
434

InterBioScreen

54. Gronowitz S., Westerlund C., Horfeldt A.B., Acta Chem. Scand. B 1976 30 391.
55. Venkatesauara Rao K., Sundaramuthy V., Proc.-Indian Acad. Sci., Chem Sci. 1976
83 238.
56. Becket G.J., Ellis G.P., Tetrahedron Lett. 1976 (17) 719.
57. Sandison A., Tennaut G., J. Chem. Soc. Chem. Commun. 1974 (18) 752.
58. Vogel A., Borman G., Ger. Offen. DE 3 438 884; Chem. Abstr. 1985 102 132271.
59. Frietze W.E., PCT Int. Appl. WO 0 011 003; Chem. Abstr. 2001 132 180596.
60. Diaz-Ortiz A., Carrillo J.R., Gomez-Escolonilla M.J., et al., Synlett 1998 1069.
61. Ono N., Muratani E., Ogawa T., J. Heterocycl. Chem. 1991 28 2053.
62. ten Have R., Leusink F.R., van Leusen A.M., Synthesis 1996 (7) 871.
63. Revial G., Lim S., Viossat B., et al., J. Org. Chem. 2000 65 4593.
64. Baruah P.D., Mukheije S., Mahajan M.P., Tetrahedron 1990 46 1951.
65. Bogdanovich-Szwed K., Budzowski A., Monatsh. Chem. 2001 132 947.
66. Strekowsky L., Aken R.V., Gulevich Y., J. Heterocycl. Chem. 2000 37 1495.
67. Charette A.B., Wurtz R.P., J. Org. Chem. 2000 65 9252.
68. Schafer H., Bartho B., Gewald K., Z. Chem. 1973 13 294.
69. Schafer H., Gewald K., Seifert M., J. Prakt. Chem. 1976 318 39.
70. Kumar A., Junjappa H., J. Chem. Soc. Chem. Commun. 1976 (15) 593.
71. Tominaga Y., Shiroshita Y., Hosomi A., J. Heterocycl. Chem. 1989 25 1745.
72. Olie S., Acta Chem. Scand., Sect. A 1970 24 2629.
73. Schafer H., Gewald K., Z. Chem. 1975 15 100.
74. Shaefer H., Bartho B., Gewald K., J. Prakt. Chem. 1977 319 149.
75. Powel J.F., US Patent 4 033 955; Chem. Abstr. 1977 87 117889.
76. Katritzky A., Adv. Heterocycl. Chem. 1976 Suppl.1 224.
77. Hamberger H., Reinsgaden H., Tetrahedron Lett. 1977 41 3619.
78. Schaefer H., Gewald K., Z. Chem. 1976 16 2721.
79. Braun O., Mohanta P.K., Jujappa H., Synlett 2000 (5) 653.
80. Mertens K., Troschutz H., Arch. Pharm. 1987 320 1143.
81. .., .., .. ., 1997 33 1044.
82. Tokumitsu T., Hayashi T., J. Org. Chem. 1985 50 1547.
83. Neumann P.N., J. Heterocycl. Chem. 1971 8 51.
84. .., .., .. ., 1979
15 1307.
85. .., .., .., . 1988 300 1133.
86. Boelle J., Gerardin P., Loubinex B., Synthesis 1997 (12) 1451.
87. Ciller J.A., Ceoane C., Soto J.L., J. Heterocycl. Chem. 1985 22 1663.
88. .., .., .., .., . ,
. . 1999 (6) 1142.
89. Prystas M., Cut J., Collect. Czech. Chem. Commun. 1977 42 269.
90. de la Creta E., Advendano C., J. Heterocycl. Chem. 1985 22 337.
91. Wolfbeis O.S., Chem. Ber. 1977 110 2480.
92. Konakahara T., Ogawa R., Tamura S., Kakehi K., Heterocycles 2001 55 (9) 1737.
93. Brimble M., Tetrahedron 1994 50 4887.
94. Thyagarajan B.S., Gopalakrishnan P.V., Tetrahedron 1964 20 105.
95. Wolfbeis O.S., Synthesis 1977 (2) 136.
96. Wolfbeis O.S., Chem. Ber. 1981 114 3471.

, 2

435

97. .., . . : . . .,
, 1989, . 1, . 1920; . 1990 4299.
98. .., .., .., . , . . 1986
(10) 2342.
99. .., .., .., 1997 (1) 89.
100. Rajappa S., Advani B.G., Indian J. Chem., Sect. B 1977 15 809.
101. Rajappa S., Advani B.G., Sreenisavan R., Synthesis 1974 (9) 656.
102. Rajappa S., Sreenisavan R., Indian J. Chem., Sect. B 1977 15 301.
103. Fisher R.H., Weitz H.M., Synthesis 1980 (4) 261.
104. Gomez-Sanchez A., Hidalgo F.J., Chiara J.L., J. Heterocycl. Chem. 1987 24 1757.
105. Mertens K., Troschutz H., Arch. Pharm. 1986 319 947.
106. Nishiwaki N., Nogami T., Tonaka C., et al., J. Org. Chem. 1999 64 2160.
107. Matsumura E., Ariga M., Tohda Y., Bull. Chem. Soc. Jpn. 1980 53 2891.
108. Ariga M., Tohda Y., Nakashima H., et al., Bull. Chem. Soc. Jpn. 1991 64 3544.

436

InterBioScreen


3-
.., .., ..
""
103787, , . , 1/4

-

[13].

,
- [4].
3- [57].

3-
.
[3,2-d]- [3,4-d]
3--4--5--2- 1 [8, 9] , ,
- - ,
1,2,3,4- 2 3, 2-()-7-3,4-[3,4-d]-4- 4 ( 1).
1 (R = H) 3.
1 (R = Alkyl, H)
3, 3,4-[3,4-d]4- 4 . 1 (R = H)
- ( ) 2
2 (, TsOH) [3,4-d]-4- 4 (R' = Me, Ph). 1 (R = H)
- ( ) (,
110, TsOH) 4 (R' = Me) ( ).
4 (R' = Me) 1
( ) [10, 11].

, 2

437

O
N

S
O

O
R'

N
H R'

EtO

R'

A:

N R
H

NH2

R' = Me, Ph
TsOH

EtO

R'
O

TsOH

TsOH

R'

S
N

B: MeC(OEt)3, AcOH

EtO

R
R'

O
R'

R"

R' = Alk, Ar;


R" = H, Alk

S
N
H

EtO

Cl

Cl

R
Cl

R'
R"

Cl
O
R" = H

2
OMe

R
NH

N
( )n
5

NH2

H
N

R=H

H2N

OEt

O
EtO

O
1

7
5

R
NH
N
N

S
6

438

InterBioScreen

3- 1 [3,2-d].
1 (R = Alkyl) 5 (O--
O-) 2,3-[3,2-d]4- 6 ( 2). R = H , 7.
7-(-2-)-5-[3,2-d]-4- 8
[3,4-d]-4- 3 ( 1)
1 (R = H; R', R'' = Alkyl). 3
(LR) [12]
9 - (, 50, 23) 3-4-(-2-) 10
11 [13]
( 3).
3

R'

H
N

R"

NH

R'

H
N
S

LR

Ar
R"

Ar

NH

OEt
S

Br

NH2

OEt
S

10

OEt
O

Ar
EtO

N
EtO

11

N
OEt

NH3

Ar

O
H

NH

S
NH2

O
8

3- 12 [9]
2 4 . .
, 2

439

R
HN

R
N
H

R
N

O
NH2

HCO2H

N
O

Ph N
H

Ph

O
N
N

Ph

NH
13

12

,
2 [3,2-d] 13 ( 4). ,
- -, [13] [14].
3-[2,3-b] 14, , . [3], 2,
[3',2':4,5][3,2-d] 15,
NHR- 4, [4,3,2-d,][4,3-d] 16 [15, 16] ( 5).
5
N
N

N
N

R'

R"

NH2
S

O 11

R = NH2,
R' = H,
R" = Ph

Ph

AcOH/H2O

R
16

N
O

14
R = OEt,
R' = R" = Me

OEt

RNH2

N R
O

15

440

InterBioScreen

[3,2-d]- [3,4-d]
3--2- 17
11 [1720] 4-[3,2-d] 18 ( 6).

R"

N R'

H2N
O

R
NH2 19

R"
HCONH2
N R'

H2N
NC

R"

R"

N R'

R' N

18
NH3

N
R'

R"

11

HN

17

HCO2H

CN

N
CN

20

4 .
CN- 17

19 2 [3,4-d] 20.
3--2,4 21 ,
CN 2. 4-
[3,2-d] 22 3-2- 23 ( 7).
3--4--2--1,5- 24 COOEt
2 [3,2-d] 25,
N 4
[3,4-d] 26 [15].
, 2

441

CN

R
R'

NH2

N
21

CN

R
N

R'

CN

N
O

R'

O
NC

NC
N
N

R
N

CN

POCl3

N
R'

OEt

23

R"NH2

CN
N

R'

NH2

OEt

11

11

CN

R
N
R'

R"

N
Cl

R"NH2

NC

N
R'

HN
22

R"

8
CN
n( )

CN

11

NH2

n( )

OEt

N
O

OEt

24

NC

n( )

n( )

RNH2

N
O
25

HN

R
N

N
O

OEt
26

n = 13

442

InterBioScreen

3--4--2--1,5- 24 11 ,
. n = 3 [3,2-d] 25, n = 1
[3,4-d] 26 [15] ( 8).

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.

Secrist III J.A., Montgomery J.A., Ealick S.E., et al., US Patent 4 985 434;
Chem. Abstr. 1991 114 185541.
Norman M.H., Chen N., Chen Z., et al., J. Med. Chem. 2000 43 4288.
Quintela J., Peinador C., Veiga C., Bioorg. Med. Chem. 1998 6 1911.
Brown D.I., The pyrimidines, New York: Wiley, 1962, vol. 12, p. 1970.
Gewald K., Chimia 1980 34 101.
Gewald K., Lect. Heterocycl. Chem. 1982 6 121.
Granik V.G., Kadushkin A.V., Liebsher J., Adv. Hetetocycl. Chem. 1998 72 79.
.., .., .., . . 1 . .
.. , , 2000, . 334.
.., .., .., .., . ,
. . 2002 (5) 789.
.., .., .., .., . ,
. . 2002 (10) 1730.
.., .., .., .., . .
3 . , , 2001, . 94.
.., . ,
. .., .., .: -, 2001, . 2, . 438.
.., 1983 52 669.
Saito K., Kambe S., Sakurai A., Midorikawa H., Synthesis 1982 1056.
.., .., .. ., .-. . 1990
12 (12) 18.
.., .., .. ., .-. . 1993
27 (910) 32.
.., .., .., .-. . 1993 27
(3) 40.
.., .., .., .., 2000
(26) 1643.
.., .., .., . 1 . .
.. , , 2000, . 32.
.., .., .., .-. . 1991 25
(12) 19.

, 2

443

,
[2,3-c]
[2,3-c]
..
-
. ..
83114, , . . , 70

, , ,
. , , ,
. 80 ; Harmala 70 . 1980 .
[2,3-c]- [2,3-c], S- O-
-, .

in vitro , S- , S- 50
. Harmala
,
, [1]. ,
, [2,3-c]- [2,3-], [2],
[38], 2- [912], , [13, 14].
, [2,3-c]- [2,3-].
, [2,3-]- [2,3-] .
1. [2,3-c]- [2,3-c]
1.1 2-(3-[b])- 2-(3-[b])
[2,3-]- [2,3-]
[1533]. [2,3-],
[b]444

InterBioScreen

3- 1, 1950 . [15]. 3,4- 2 50 90%. (R' H) POCl3


[20, 27] P2O5 [15, 2332]. R' = H
() [11, 16, 17, 19, 22]. 1 (R' = H)
P2O5POCl3 2 ( 52%) 3 ( 20%, 1) [26].
1

R"
R
X

HN

+
H

R"
R

X
2

R'

R'

[H]
2H

R"
R

NH

X
4

R'

R"
4H

X
3

R'

R = H, Alk, , CI, Br, I; R' = H, Alk, OH, Ar, Het;


R'' = H, CO2Alk; X = O, S

[2,3-c] [11, 15, 16, 1820, 3234]. [1619, 22] 100 ( 70%),
90 ( 90%) [34], [20, 3638], [35].

10% [37].
3,4- 2 1,2,3,4- 4 [2832] [21, 27]
( 8095%).
2 3
190200 ( ) [22, 37, 38],
[26], (Pt2O) (190200) [23].
4 260270 Ph2S2,
, , [39, 40].
3,4-[2,3-c]-1(2)- 6 N--2-(3-[b]) 5 POCl3P2O5 ( 61%)
8 ( 70%) [41, 42]. 6
1,2,3,4-[2,3-] 7 [41, 42] ( 2).
, 2

445

2
POCl3

HN

S
5

P2O5

OEt

LiAlH4

NH

NH

NOH

6--3,4-[2,3-c]-1(2)- 10 9 [43] ( 3).


3

MeO

HCl

MeO

NCO

NH

10a

3-(2-)[b] -[b] 11 12
13 [20, 4345] ( 4).
4
R" +
R

X
11

R'

R"

R"

NH

X
12

R'

4H

X
13

R'

R = , Alk, OAlk, CI, Br, I; R' = H, Alk, Ar; R'' = H, CO2Alk; X = O, S

11 - (, ) ( 90%) [20, 44].


3-(2-)[b] 11, in situ 3-(2-)[b] 16 446

InterBioScreen

[20, 21, 26, 27, 44, 4649]. 12 ,


[20, 44].
3-[b] 16 , , 14 ( 97%) [46, 47].
14 7 N- 15.
15 95% 14
, .
14 7 . 7
14 (90%). 16
(R = CH3)
15 9394% ( 5).
5
HCOH

HN

16

14

HCOH/HCO2H

NH

15
HCOH/HCO2H

R = H, Me

, [47] ,

3-(2-)[b] 16 (R = H)
7, , , 14. 14 7 ,
N- 15.
7 15.
1.2
[2,3-c] [2,3-c] 17
18 [5052]. 17
POCl3 90100 [50]. 18 4- , 2

447

20 90% 6N HCl
(1 : 1) [51, 52]. 21 (R' = CH3)
( )
4-[2,3-c]
22 95% [53]. R' = H 05
; 22 75%
[54] ( 6).
6

OR
OR
X

POCl3

19

17

OR
OR
X

OH
AcOH
HCl

R'

18

R'

20

OH
Ar
X

Ar
+
H

R'

21

R'

22
R' = H, Me; X = O, S

21 (R' = H)
30%- ,
22 (R' = CH3) 75% [54].
1.3 2-(2-)
[2,3-c] [2,3-c]
2-(2-() 23 [5557].
. 4-()[2,3-] 25 4-()[2,3-b] 26. ,
24 [57] ( 7).
448

InterBioScreen

C 7
R'
Bu
R
Cl

Bu
N

Cl

O
R'

NX

R=H

Bu

25

R'

R = Ph

Ph
23

R'

24

Cl

26

R' = Ph, SiMe3; X = O, S

1.4 - [2,3-c]

1,3- [2,3-c] [2,3-c] 28
[2,3-c]- [2,3-c] 27
. R' R'' ,
. 9095% [5860] ( 8).
C 8

R
R"

X
27

NH3

R"

R' ClO4

28

R'

R, R' = Alk, Ar; R" = Me, Cl; X = O, S

- 1- ()[2,3-] 29 [61, 62].

X
29

R = Alk; X = O, S

, 2

449

[2,3-] 30.
. , 27
30, 1-R'''- 31. 30 1-R'''- 31 [63] ( 9).
9
R'

R"
+

O ClO4

S
27

R
R'"NH2

O
R"
S

R'

O
R"

R'"
N

R'
R'"
NH

R"

R"

R'

R'

S
30

N
R

R"'

ClO4

R
HN

31

R"'

R = H, Me; R' = Me, Ph; R'' = H, Me, Cl; R'" = Me, Ar, Bn, CH2CH2OH

[2,3-] , .. , N--1,3-[2,3-] 32 , 5-[2,3][2,3-] 33. 1,3- [2,3-]


N- 32. [2,3-] 27,
1 3 , N- 32
33 [64] ( 10).
450

InterBioScreen

10

R"

ClO4

R'
+

R'

R"
+

S
27

S
R"'NH2

ClO4
R

32

NH2

R'

R"

N
N

33

R
R = H, Alk; R' = Me, Ph; R'' = H, Me, Cl

1--3(2)()[2,3-] 34 1--N--3(2)()[2,3-] 35
3--(3-, 3-)[2,3-] 27 1--3-[2,3-], ([2,3-])
[65, 66] ( 11).
11
O

X
R
+

X
27

Ar

35

ClO4

X
a - R = NHAr; X = O, S;
b - R = OH, NMe2, C4H8NO; X = O;
R = OH; X = S

NH

34

, 36 10b 7080% [67] ( 12).


, 2

451

12
R

R
O

O
36

NH

10b

R = H, CO2H

3- 37a, b 1--3(2)()[2,3-] 38a, b [65]


( 13).
13

AcONH4

NH

38a, b

37a, b

a X = O, b X = S

1.5
2--5-[b]-3- 39 ( : POCl3 = 6 : 1) 40 (60%) [68]
( 14).
14
OH

O
MeO

O
/POCl3

OH

O
39

OH

MeO
N

O
40

39 41 10%- -6--4,9-[2,3-c]-1,3(2,4) 42 [69] ( 15).


452

InterBioScreen

15

OH

Cl

10 % NH4OH

O
NH

OH

41

Cl

42

2--3-[b]-1,1- 43

4--2--1-[2,3-c]-9,9- 44 50% [70] ( 16).
16
O
Cl
S
O O

OEt

O
Ph

OEt
H2N

S
O O Ph
44

43

[2,3-c]
() 3-[b]-2-
[7174] ( 17).
17

Cl
H
N

O
45

NH

S
46

2.
2.1
[2,3-]- [2,3-] . , -
[75], [2,3-]- [2,3-] , 2

453

[76].
2.1.1
[2,3-]- [2,3-]. ,
[2,3-c] 47 6- 48, 48 49 [77, 78].
, 1,3-[2,3-c] 47a 99%
50 1,3--6-[2,3-c] 48a (97%) 1,3--6,8-[2,3-c] 49a (3%).
47a (85%)
6- 48a ( 89%). 48a
, 56% 47a.
47a 99%
05 48a 49a (%) 55 : 45.
1--3-[2,3-c]
47b [77] ( 18).
18
HNO3 O2N

S
47a, b

O2N
S
NO2 49a, b

48a, b

R = Me, b R = Et

6 8
(, ), .
1,3,6-[2,3-] 47c 1,3,6--5-[2,3-c] 50 (88%)
8- 51 (8%) 5,7- 52 (4%).
1,3,8-[2,3-] 47d 1,3,8-6-[2,3-c] 53 ( 73%) [77] ( 19).
19
NO2

NO2

S
47c

454

+
O2N

50

NO2
51

52

InterBioScreen

O2 N
N

S
53

47d

1--3--6-[2,3-c] 54 1,3,6-[2,3-c] 47c.


5, 7 8 55ac.
54
80 [77] ( 20).
20

NO2

Cl

Cl

Cl
N

Cl

HNO3

O2N

Pr

NO2
55a

54

55c

55b

[2,3-c] 56a, b ,
[2,3-c]. 1,3-[2,3-c] 56a 6- 57a.
1,3,7-[2,3-c] 57b. 6
, 1,3,6-[2,3-c] 56c,
8 57c [79] ( 21).
21
HNO3

O2N

56a, b

57a, b

HNO3

O
NO2

56c

57c

a R = H, b R = Me

1-()-3-[2,3-c] 58a, b ,
, 2

455

3- . , 58a 99%
1820 6- 59a,
58b 99%
59b,
- 3- [79] ( 22).
22

HNO3

O
58a

O2N
N

Et

Et

59a

NO2
HNO3 O2N

H2SO4

58b

59b

1,7-[2,3-c]-3(2)- 60a 1-[2,3-c]-3(2)- 60b 85%


1015 4- 61a, b.
99%
4,6- 62 [77, 80] ( 23).
23
NO2

HNO3
AcOH

R
O
R

X
60a, b

NH

NH

61a, b
HNO3
H2SO4

NO2

O2N

X=O
R = H, Me; X = O (a), X = S (b)

456

NH

62

InterBioScreen

2.1.2
[2,3-c]
(
)
100110 [81].
, 1--3-[2,3-c]
47ac, e 8- 63a, ( 24).
24
R'

AcCl
AlCl3

R'
N

47ac, e

63ac, e

63: a R = Me, R' = ; b R = Et, R' = ; R = R' = Me; e R = Me, R' = Cl

8 , 1,3,8-[2,3-c] 47d 1,3,5,8-[2,3-c]


47f, 6 64a, b ( 25).
25
R

O
R'

R'

Cl

AlCl3

47d, f

64a R = H;
64b R = Me

R' = Me, Ph


47a 4-.
6 8, (6)- 61 [81]. 65 : 66a (Ar = Ph)
65b : 66b Ar = 4-ClC6H4 % 81 : 19 63 : 37 ( 26).
26

O
ArCOCl

Ar

AlCl3

47a

65a, b

Ar

66a, b

65, 66: a Ar = Ph; b Ar = 4-ClC6H4

, 2

457

[2,3-c] 56
130135 .
[2,3-c]
,
100110 30%. ,
6-[2,3-c]
6769 [79] ( 27).
27
O
R"
R

R'

R'

56ac
6769
67 R = H, R' = R'' = Me; 68 R = R' = Me, R'' = Ph; 69 R = H, R' = Et, R'' = Ph

1--3-[2,3-] 58a , 6- 70. , 6


, - 3-
( 71) - ( 72) ( 28).
28

Ac
N

O
70

Et

Ac

Ac
N

O
58a

Et

71

Et

Ac

Ac
N

O
72

458

Et

InterBioScreen

1,7--3(2)[2,3-c] 60a
AlCl3 130135 6- 73. 60a
74, 4
6. 74
,
[80] ( 29).
29

O
O

AcCl

O
O

NH

O
73

NH

O
PhCOCl

60a

Ph
O

Ph
O

NH

74

4-()- 1,7--3(2)-[2,3-c] 3-() 75a, b. ,


6- 73 64% 60a.
3- 75b 6- 76 85% [80] ( 30).
30

O
R

O
O
75a, b

R
O

NH

73 R = Me;
76 R = Ph


[2,3-], [2,3-] [2,3-].
" " [80].
-
[2,3-] , , 2

459

, 2M COSY 2DJ,
, [82].
2.1.3
1,3- - [2,3-]
. 1-3,3,6--1,2,3,4-[2,3-] 29 6- 77
78.
,
2--1--3,3,6--1,2,3,4-[2,3-] 79 [78] ( 31).
31

O
29

Br2

O
Br

Br

Br

78

77

Br
O

O
79

60a 4-()
80a, b [80] ( 32).
32
R
O
O

NH

60a
a - Br2, AcOH, AcONa;
b - KSCN, Br2, AcOH

460

a, b

NH

80a R = Br;
80b R = SCN

InterBioScreen

1,7--3-[2,3-c] 75a, N- 1- ,
79% 1- 81 [80] ( 33).
33
O
O
75a

Ac

NBC
CCl4

O
81

Ac

N
Br

3. [2,3-c] [2,3-c]
- [2,3-c] . [2], [38], 2- [912],
[13, 14]. ,
- [2,3-c]
[38, 11, 2831, 42, 8387].
[2,3-] [2,3-] 28, 29
. ,
[2,3-] , [88, 89]. [2,3-]
. 28 29
[61]. ,
, 10 /.
[2,3-]- [2,3-], , , .

1.
2.
3.

Campaigne E.E., Knapp D.R., Neiss E., Bosin T.R., Adv. Drug Res. 1970 5 1.
Bowersox S.S., Singh T., Wang Y.-X., PCT Int. Appl. WO 9 827 984; Chem. Abstr.
1998 129 100057z.
Kawakubo H., Nagatani T., Ueki S., PCT Int. Appl. WO 9 321 189; Chem. Abstr.
1994 121 9382a.

, 2

461

4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.

462

Kawakubo H., Hase T., Ueki S., Jpn. Patent 5 163 278; Chem. Abstr. 1994 120
270355b.
Kawakubo H., Jpn. Patent 7 109 281; Chem. Abstr. 1995 123 285988w.
Kawakubo H., Nagatani T., Ueki S., PCT Int. Appl. WO 9 413 679; Chem. Abstr.
1995 123 340082y.
Kenis L.E.J., Bischoff F.P., Mertens C.J., et al., Bioorg. Med. Chem. Lett. 2000 10
(1) 71.
Takada S., Fukui K.S., Sasatani T., Jpn. Patent 10 298 180; Chem. Abstr. 1999
130 38288r.
Kenis L.E.J., Keybus F.J.E., Mertens C.J., PCT Int. Appl. WO 0 020 421; Chem.
Abstr. 2000 132 265187s.
Grunewald C.L., Caldwell T.M., Dahanukar V.H., et al., Bioorg. Med. Chem. Lett.
1999 9 (3) 481.
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109 110430s.
Volante R.P., Desmond R., Shinkai I., Eur. Patent 251 713; Chem. Abstr. 1988
109 6495f.
Kawakubo H., Kawasaki M., Jpn. Patent 7 145 054; Chem. Abstr. 1995 123
208784z.
Bosin T., Bitner R.S., Gadbois T.M., et al., PCT Int. Appl. WO 8 912 477;
Chem. Abstr. 1990 113 59150d.
Herz W., J. Am. Chem. Soc. 1950 72 (11) 4999.
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148446q.
Baldwin J.J., Huff J.R., Vacca J.P., et al., Eur. Patent 204 254; Chem. Abstr. 1987
106 76431n.
Huff J.R., Baldwin J.J., Vacca J.P., et al., Eur. Patent 214 556; Chem. Abstr. 1987
107 23254c.
Baldwin J.J., Huff J.R., Vacca J.P., et al., US Patent 4 710 504; Chem. Abstr. 1988
109 73354x.
Kawakubo H., Hase T., Jpn. Patent 61 236 779; Chem. Abstr. 1987 106 67284w.
Clarke K., Hughes C.G., Humphries A.J., Scrowston R.M., J. Chem. Soc. C 1970
(8) 1013.
(a) Huff J.R., Vacca J.P., Baldwin J.J., US Patent 4 690 928; Chem. Abstr. 1988 109
23864p; (b) Pendelton R.G., Eur. Patent 216 247; Chem. Abstr. 1987 107 70814v.
Martin-Smith M., Reid S.T., J. Chem. Soc. C 1967 (19) 1897.
Campaigne E., Homfeld E., Mais D.E., J. Heterocycl. Chem. 1978 15 1351.
Ruffin L.D., Bowlus S.B., J. Heterocycl. Chem. 1983 20 461.
Shafiee A., Mohammadpour-Toiserkani M., J. Heterocycl. Chem. 1979 16 653.
Wolf G., Zymalkowski F., Arch. Farm. 1976 309 (4) 279.
Suh J.T., US Patent 3 651 068; Chem. Abstr. 1972 77 34480m.
Suh J.T., SA Patent 6 801 235; Chem. Abstr. 1970 72 90427h.
Suh J.T., US Patent 3 767 659; Chem. Abstr. 1974 80 27233s.
Suh J.T., US Patent 3 520 895; Chem. Abstr. 1970 73 130980n.
Suh J.T., US Patent 3 626 068; Chem. Abstr. 1972 76 46185m.
Bosin T.R., Maickel R.P., Dinner A., Campaigne E., J. Heterocycl. Chem. 1972
9 1265.
InterBioScreen

34. Volante R.P., Desmond R., Shinkai I., Eur. Patent 251 713; Chem. Abstr. 1988 109
6495f.
35. Jaeggi K., Renner U., Ger. Offen. 1 945 161; Chem. Abstr. 1970 72 121352m.
36. Fr. Patent 1 339 382; Chem. Abstr. 1964 60 2932a.
37. Kyburz E., Pletscher A., Staebler H., et al., Arzneim.-Forsch. 1963 13 (9) 819.
38. Brossi A., Kyburz E., Belg. Patent 624 518; Chem. Abstr. 1964 60 2932.
39. Nakasaki M., J. Chem. Soc., Pure Chem. Sect. 1953 74 403.
40. Kotake H., Sakan T., J. Inst. Polytech. Osaka City Univ. C 1951 2 (1) 25.
41. Suh J.T., Ger. Offen. 2 000 775; Chem. Abstr. 1970 73 120599f.
42. Chapman N.B., Hughes C.G., Scrowston R.M., J. Chem. Soc. C 1970 (16) 2269.
43. Fournier C., Boyer F., C. R. Acad. Sc., Ser. C 1970 270 (13) 1179.
44. Ueki S., Kawakubo H., Okazaki K., Nagatani T., PCT Int. Appl. WO 8 802 751;
Chem. Abstr. 1988 108 149508y.
45. Bottcher H., Hausberg H.H., Seyfried C., Mink K.O., Eur. Patent 206 225;
Chem. Abstr. 1987 106 119964b.
46. Bosin T., Bitner R.S., Gadbois T.M., et al., Adriaenssen P.I. WO 8 912 477;
Chem. Abstr. 1990 113 59150d.
47. Campaigne E., Homfeld E., J. Heterocycl. Chem. 1979 16 1321.
48. Suh J.T., Ger. Offen. 2 000 775; Chem. Abstr. 1970 73 120599f.
49. Suh J.T., SA Patent 6 908 358; Chem. Abstr. 1972 77 48433k.
50. Herz W., Tsai L., J. Am. Chem. Soc. 1953 75 (20) 5122.
51. Frehel D., Maffrand J.P., Fr. Patent 2 400 518; Chem. Abstr. 1979 91 175318r.
52. Boigegrain R., Maffrand J.P., Fr. Patent 2 414 048; Chem. Abstr. 1980 92 110987j.
53. Brenner L.M., US Patent 4 282 227; Chem. Abstr. 1981 95 187224c.
54. Schneider C., Weber K.-H., Langbein A., et al., US Patent 4 322 423; Chem. Abstr.
1982 97 23769z.
55. Stoll W.A.W., Marcelis A.T.M., Koetsier A., van der Plas H.C., Tetrahedron 1989
45 (20) 6511.
56. Haider N., van der Plas H.C., Tetrahedron 1990 46 (10) 3641.
57. Tahri A., Borqgraeve W.D., Buysens K., et al., Tetrahedron 1999 55 (51) 14675.
58. .., .., .., 1981 (10) 1351.
59. .., .., 1987 (7) 889.
60. .., 1998 (10) 1335.
61. .., .., .. ., 1994 (3) 321.
62. .., .
, , 1998, . 106.
63. Tolkunov S.V., Kryuchkov M.A., Tolkunov V.S., Dulenko V.I., Proc. Int. Conf.
Reaction Mechanims and Organic Intermediates, S. Petersburg (Russia), 2001,
p. 212.
64. .., .., .., .., 1998 (8)
1137.
65. .., .., .., .
, , 1999, . 37.
66. .., .., .., 1991 (11) 1152.
67. Chatterjea J.N., Sahari R.P., Swaroopa B.B., et al., Chem. Ber. 1980 113 (11) 3656.
68. Waykole P., Uscaonkar R.N., Indian J. Chem., Sect. B 1984 23 (5) 478.
69. Witiak D.T., Loh W., Feller D.R., et al., J. Med. Chem. 1979 22 (6) 699.
, 2

463

70. Reid W., Mavunkal J.B., Chem. Ber. 1978 111 (4) 1521.
71. Castle S.L., Buckhaults P.J., Baldwin L.J., et al., J. Heterocycl. Chem. 1987
24 1103.
72. Kudo H., Takahashi K., Castle R.N., J. Heterocycl. Chem. 1987 24 1009.
73. McKenney J.D., Castle Jr., Castle R.N., J. Heterocycl. Chem. 1987 24 1525.
74. Stuart J.G., Khora S., McKenney J.D., et al., J. Heterocycl. Chem. 1987 24 1589.
75. .., .., .., ..,
-. , : , 1992.
76. Cocer J.D., Gregory G.I., Ger. Offen. 2 022 024; Chem. Abstr. 1971 74 141731d.
77. .., .., .., 1993 (5) 706.
78. .., .., .. ., 1995 (8) 1124.
79. .., .., .., .., 1995
(5) 694.
80. .., .., .. ., 1996 (4) 534.
81. .., .., .., .., 1994
(5) 701.
82. .., .., .., 1997 (9) 1199.
83. Kawakubo H., Okazaki K., Nagatani T., et al., J. Med. Chem. 1990 33 (11) 3110.
84. Kawakubo H., Takagi S., Yamaura Y., et al., J. Med. Chem. 1993 36 (23) 3526.
85. Bosin T.R., Campaigne E.E., Adv. Drug Res. 1977 11 191.
86. Kubo K., Ueno Y., Jpn. Patent 04 154 785; Chem. Abstr. 1992 117 212480r.
87. Ueki S., Kawakubo H., Okazaki K., Nagatan T., US Patent 5 126 948; Chem. Abstr.
1992 117 212482t.
88. .., .., .., ..,
, , 1998, . 91.
89. .., .., .. ., . . 770 056,
. . 1985 (12) 25.

464

InterBioScreen



..


344090, --, . , 194/2
1.
-
().
.
- 1 - 2, 3, 4 5 [14], [5].

NR2

NR2
R'
O

NR2
H

R'
N

NR2
H

R'
O

Ts

N
H

R2
R'
N
4

Ts

N
H

R
R'
O

NR2
H

1 [6] 5 [3]

-.
.
,
, [7].
5-
(pKa = 8.33) [2]. ( ~ 11)
, [8]. ,
, 2

465

,
.

O
H

H
NO2

NO2


. 3--5- 3,5- [9].
5--2-.
, CCl4 [10].
2. [3,3,1]
- 6 .
,
N- 6,12-[b,f][1,5] 7 [11, 12] ( 1).
1

O
H

2R

SH
6

R'NH2

2H2O

NR'

S
7

5,12--6,12--6,12-[b,f][1,5] 9af - 8 9 9bf PrOH HOAc [13, 14] ( 2).


466

InterBioScreen

Ts

O
H

, PrOH AcOH

RNH2

NR

2H2O

NH

Ts

Ts
9af

8
SO2NH2 (d),

R = H (a), Me (b), Et (c),


O H
S N
O
S

O H
S N
O

(e),
N

(f)
N
OMe
N

MeO

9 - 4, 8
4 [13] ( 3).
3

2
N

N
H

AcOH,
RNH2

i-PrOH,
H2O

Ts
4

.
[15, 16], 2--5- 10
4 , N- 6,12-[b,f][1,5] 11 ( 4).
4

O2 N

NR

Ts

O
H

HN

Ts

H2O

SH
4

10

O2N

NR
S
11

R = Me (a), Et (b), Bn (c)

, 2

467

- 10 ,
N- 6,12-[b,f][1,5] 12, 5- [16] ( 5).
5
N
10

Et

O2N

O 2N
OH

NEt

H2O

NO2

3a

12

2--1- 13
1020% 7,15--7,15-[2,1-b,f][1,5] 14 [17] ( 6).
6
O

H
OH

RNH2HX

Py,

NR

2H2O

O
14

13
R = Me (a), Et (b); X = Cl, Br

-
, -,
,
. , ,
"",
15 [16] ( 7).
7

Ts

N+

O H
H RN

Ts

Ts
N

HO

H2O

N
Ts

NHR

15

468

InterBioScreen

Ts
N
NR
N
Ts

3.


[18] ( 8).
8

H
N

+
H

H
N+
H

16 [19] 17 1,3- 20 [20] ( 9).


9
R + I
HN R

R
N R
R'
N R
R

CuI

Ph

MeCN

R'
N R
R

CuC

18

17a

16ac

Ph

Ph

R'

N R
R

R2NH

R
CuC

Ph

CuI

N
R'

19ac

20ac

a R' = Ph, NR2 = ; b R' = 2-, NR2 = ;


c R' = p-MeOC6H4, NR2 =

, 16, HI, 18 19,


, 2

469

.
- .
. 3--2--3-
-
,
, 1,3- ,
3--2--3- [2].
1a, b CuI 20d, e ( 10).
10

Ph

MeCN,

OH

CuI

OH

1a, b

17a

Ph

N
H

20d, e

X = CH2 (a, d), O (b, e)

5- 1
2--3--5--3- 21, CuI
20f ( 11).
11

O2N

NR2 = N

470

OH
20f

R
O2N

CuI
MeCN,
O

Ph

22a

OH
1c

O2N

N
H

N R

N R
Ph

O
21a

+
N
H

InterBioScreen

5-
,
3--2--3- 21be ( 12).
12
X

X
R'

N
R

N
OH

CuI

R'

MeCN,

+
N
H

1ac

21be

17bd

R = NO2, R' = CH2OH, X = O (b);


R = H, R' = CH2OPh, X = O (c);
R = NO2, R' = CMe2OH, X = O (d);
R = H, R' = CMe2OH, X = CH2 (e)

R' = CH2OH (b);


R' = CH2OPh (c);
R' = CMe2OH (d)

21 -
1,3- [21]. 21
, , 1,5- [21].
21dh. , [22],
23 ( 13).
13

HCO2H,

O
R'

OH
R"

21dh

R"'

H
R'"

H2O

O
R"

R'
22

, 2

471

X
N

R"'
O
R"

R'
23dh

21: f R = NO2, R' = H, R''+R''' = (CH2)4, X = O;


g R = R' = Cl, R''+R''' = (CH2)4, X = O;
h R = R' = Br, R''+R''' = (CH2)4, X = O;
23: d R = NO2, R' = H, R'' = Me, R''' = H, X = O;
e R = R' = H, R'' = Me, R''' = H, X = CH2;
f R = NO2, R' = H, R''+R''' = (CH2)4, X = O;
g R = R' = Cl, R''+R''' = (CH2)4, X = O;
h R = R' = Br, R''+R''' = (CH2)4, X = O

b. 3--2--1--3-
- 2
CuI, 3--2--1--3- 24.
2a, c, d 17
25ac, 2 17d 25d [23] ( 14).
14

NR2

NR2

NR2

OR'

CuI

OR'

NHTs

MeCN,

N
Ts

17b, c

2a, b

472

NR2 = N

O (a);

NR2 = N

(b)

24ac
R' = H, NR2 = N

O (a);

R' = Ph, NR2 = N

O (b);

R' = Ph, NR2 = N

(c)

InterBioScreen

R2N

2a, c, d

CuI

NHTs

MeCN,

17a, d

25ad

(c);

NR2 = N

NR2 = NEt2 (d)

NR2 = N

O (a, d);

NR2 = N

(b);

NR2 = NEt2 (c)

R = Ph (17a, 25 ac), CMe2OH (17d, 25d)

24 [24], ,
, ,
.
25 26 27 ( 15).
15

R
H2SO4

N
26

25a

KOH

Ph

N
NR2 = N

Ph

27

. 2- 1,2-
, 21dh
[22], - , [25].
1 17 CuI 2--3--5- 30 3-2--6--2- 36 ( 16). ,
[2] - 28 Z- 31
2--3--5--2,3-. ,
Z- ( = 1.61 1). -
s-- , 28 30 ( 16, ).
=-=
Z-, .
, 2

473

, 2--3--4--2,3- ,
31 N (2)
32, 2- 36 ( 16, b). ,
-, .
16
R
OMe

O
1c

CuI

O2N

MeCN,

R
O
H

R
OMe

O2N

O2N

R
OMe

28

O2N

N R

O
OMe

O N R
R

O
MeO

33

32

O
O2N

34

MeO

30

O2N

OMe

31

O2 N

29

O
31

R
N HO

R
H
+

28

:N

17e

N
R

OMe
R

O2N
O
35

N
R

OMe
R

O
O2N
O
NR2 = N

474

36a

N
R

OMe
R

InterBioScreen

CuI 1 17
, 2- 36
80%. 30 ().

Z- 31. 1 2- 17f ( 17).
17

O2N

1c

O
17f

NR2 = N

N
R

36b

O
R

2- 36f 17 17f 1d, e


( 18).
18
R
R'

N
R
OH

O
R

17e 17f
O

N
R

NO2

NO2
1d, e
R = H (d);
R = OMe (e)

NR2 = N

O;

R''
R

36cf
R' = H, R'' = OMe (c);
R' = H, R'' = CHMe2 (d);
R' = R'' = OMe (e);
R' = OMe, R'' = CHMe2 (f)

5- 37 [8] 17e, f ( 19).


19

O
O2N

O
H

O
37

17e 17f

O2N

R
O

NH2

36
R = OMe (g); CHMe2 (h)

, 2

475

1,2-.
[26], 5--2- 2
17e, f ,
3--2--6--1--1,2--3- 38
2--6--3-(-2-)-1--1,2--3- 38b,
( 20).
20
R

O2N

N
O

NH

O2N

17e 17f

Ts

N
R

Ts

38a, b
R' = OMe (a), (83%);
R' = CHMe2 (b), (56%)

2e
NR2 = N

R'
R

, Z-
3--2--3- 39 31 ( 16). , : 39 40
41 42 43 38 ( 21).
21
O

2e

:N

O2N

17e

17f

O
H

O2N

Ts R

Ts R
39

40

O
R

N
41

476

O2N

O2N

Ts

R
N

Ts

N
O

42

InterBioScreen

O
O2N

H
R

38

N
O

Ts

43

4. -
2-
4- - ,
[27, 28].
,
[27, 28], [29].

. 2,6-- 44 45 46 2080% [29] ( 22).
22

OH
OH

RC6H4CH N

170180C

X
2

0.51

C6H4R

N
X

44

45

46
R = o-OH, X = O (a);
R = o-OH, X = CH2 (b);
R = H, X = O (c);
R = p-MeO, X = O (d)

46, b [30]
- ,
47, 48 ( 23).
, 2

477

23

OH

H
X

h,

R'

N
X

R'

HO

N
H

O
R

46

47

O
X

+
N
H

R'
HO
R

48

46 , 2,6----4--4-(2-)-2,5- 49 [31].
, 50 ( 24).
24

OH
O

KOH

N
HO
46a

478

N
H

K3[Fe(CN)6]

H O
49

N
H

50

InterBioScreen

49 2,6---4--4-(2-)-2,5- [32].
46 53a, b [3] 51 52 ( 25).
25
OH
H
N

OH
OH

51

R
O

ZnCl2,

R
O

52

N
H

53
R = H (a), R = Br (b)

53 46 2,6--- 2--1- -
, .
53 - ,
54, 55 ( 26).
26

53

h ,

OH

+
N
H

+
N
H

54

55

2--1- 56
-.
, 2

479


4-N--1,2- 57, 2-1- [a,j] 58 [33] ( 27). . [33].
27

H
OH

O
O

HO

56

Ar

N
H

57

58

- 52 58
56 52.
[34] .
, 1
- 52 2--1-(2--5-) 59, (2--1-)(2-5-) 60,
12-(2--1-)-10--12-[a] 61 ( 28).
28
H
N

1c

52a

OH
O2N

N
OH

O
O

59

OH
O2N
O

N
H

OH
O
O2N

52a

O2N
OH

OH OH
60

480

InterBioScreen

OH
MeNO2,

O2N

H2O

O
61

60 ,
.
1
2-, 62
63 [35] ( 29).
29

R''
R'
N
H

R
N

R
N

OH

HN

N R
R
62

R
OH

R''
R'

R''
1

R'

N
H

NR2 = N

OH

HN

N R
2

63

[19b], , - . 62
,
, - 64. ,
63 30.
, 2

481

30

H
N

H
N
O

R'
O
R

R'

N
H

N
H

N
H

O
R

62

64

H
N

H
N

H
N

H
N
O

O
R'

R'
OH
R

H2O

N
H

63

O
5. -

, , , , , [18].
1 65, 4- 66 [6]. , ,
,
9--1,2,3,4--9- 67 ( 31).
31
R''

R
R
N
N
O
O
R
R
N
R'
R
R
OH
66

+
R''

NR2 = N

482

R'

R
65

R''
O
R'

67

InterBioScreen

32,
[6], - 68, 69
70. ,
66,
71 ( 32).
32

R
N

R
N

R
R
OH

R
O

R''

X
O

R''

N
H

R'

R'

65

+
68

R''

O
R'

R'
69

70

R''

R'
66

NR2 = N

R''

N
H

R''

R'

N
H

71

65, 5- , 37 69 ( 33).
33
+

O
O2N

H2NR'2

O2N

H
+

O H2NR'2

37

, 2

69

483

+
O H NR'
2
2

O2N

O2N

H2O

O
N
R
R

R'2NH

O
N
R
R

NR2 = N

65

4-7--2,3--1- 71 ( 34).
34
1c

PhCN,

O2N

69a

71a (33 %)

72 74 - 73 [b]-2- 75 [36]
( 35).
35

R
N

R
N

O
72
120C, 2
(R = R' = Cl)

R
OH

Cl

1d (R = R' = Cl);
1e (R = R' = Br)

O
74

R''

145C, 2

R'
NR2 = N

O
N
R
R

73 (58%)

R'

R''

Cl

O
N
R
R

75a R' = R'' = Cl (47%);


75b R' = R'' = Br (39%)

( 36).
36
1d

145C

73 (70%)

76a

484

InterBioScreen

74,
77 5- 1.
- [b]-2-, 75,
2,2'- 82 [36].
( 37) 80
32 [4+2]- 76 78
79 80,
2,3- .
3,3'--2,2'- [37]. 80
78 , 2- , 81 82. , 4-7--1,2,3,4--4-
. -, 79 7-
8- ,
( 37).
37

R
O
1c +

( )n

R R

O2N

O2N
( )n
O
2
N
N
R
R
H

( )n
76b n = 3;
76c n = 4

78

O
74 n = 3;
77 n = 4

79

NO2

NO2
O
N

n( )

O
O

78
n( )

n( )

O
O

N
H

O 2N
NO2
80

81
NR2 = N

, 2

NO2
82a n = 3;
82b n = 4

485

20f 83 84 1-,
[36] ( 38).
38

R
O2N
O

O
N
H

150170C
2

H
N

O2N

+
O

N
O

84a (36 %);


84b (82 %)

20f 83
(20f, 84a),

R=

N
H

Me (83, 84b)

O
20f 83

130140C

2 .

84a (66%) 84b (51%)

2d

85 5- [36] ( 39).
39

O2N

+
OH

120155C

O2N

12

O
HN

85
R = Et (a); Pr (b);

(c); Bn (d);

(e)
O

, 5- 86 87. (
), 88, 85 ( 40).
486

InterBioScreen

40
O
3ae

O2 N

HN

OH

87

86

OH
O2N
O
HN

H2O

85

88

88 [38].

- .

. [3, 6, 30]. , , .
. ,
,
. . ,
, 41.
41

R'
R''
O

R'

R R
N
H O

R''
O

89

NR2
R'

R'
H2O

H
H
H O

R''

R''
O

NR2

, 2

NR2
487

R' = NR2, 89 , R' .


, 85
90,
( 42).
42
H
O2 N
O

OH
O2 N

O
H
R

NH

NH

90

OH
O2N
O
NH
R

H2O

85

6. -2-
- . -2-, ,
91 [39].
1- 69,
4,11--1,2,3,4,11,11--4-[1,2-a] 92 [40], .. ,
. , , -, . ,
91
[39]. ,
. 68 ,
91 , 92 ( 43).
44.
N(5) N(12) C(6) C(13) (q),
- 3 91,
.
488

InterBioScreen

43

O
O

OH
N

N
N

+4

N
N

+2

OH
68a

91

92


, .
( ) .
44

O
O

N
N

13

12

N
N

N
N

O
N(5,12)
C(6,13)

N
N

q
-0.052
0.065

92

91 1- : 92 4--3,10--1,2,3,3,4,9,10,10-[1,2-a] 93 2(2--4,5-) 94 [40, 41]


( 45).
45

R
R
91

R
N

N
NR2 = N

N
R

93

, 2

NH
94

489

, 94
,
[42], 93, , .
7. 4--1,2-
1,4- - 1,4- [43]. 57 [33] 68
7--5--7,8,9,10,11,11-[b][1,2-][1,4] 91 [44] ( 46).
46

N+

X
68

57

O
N+

N
O
91

X = O (a), CH2 (b), NMe (c)

91 2 , . 1 .
- 57
, 5-[a] 92 ( 47).
490

InterBioScreen

47

NH2
57
NH2

AcOH

N
N

N
92

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.

. ", , , ", --:


- , 1967.
.., .., .. ., . , . . 1994
(3) 455.
.., .., .. ., . , . . 1992
(10) 2389.
.., .., .., . , . ., .
., , .: , 1977, . 10 [Bell R.P., The Proton in
Chemistry, London: Chapman and Hall].
.., .., .., .., . , . .
1999 (5) 959.
Opitz G., Lschmann I., Angew. Chem. 1960 72 523.
.., .., .. ., . , . . 1995
(5) 940.
.., .., .
Khrustalev V.N., Lindeman S.V., Ukhin L.Yu., et al., Z. Kristallogr. 1988 213 296.
.., .., .., 1975 11 (4) 836.
orrigan M.F., West B.O., Aust. J. Chem. 1976 29 (3) 646.
.., .., .. ., 1988 303 (3) 646.
.., .., .., . , . . 1997 (11) 2035.
Ukhin L.Yu., Komissarov V.N., Korobov M.S., Nivorozhkin L.E., Mendeleev
Commun. 1991 71.
.., .., .., .., 1992 28
(2) 408.
.., .., 1991 27 (4) 885.
Tramontini M., Synthesis 1973 (12) 703.
-, , .: ,
1968, . 481 (), . 495 (b).
.., .., .., .., 1987 23
(6) 1325.
.., ..,
, : , 1983, . 49.
.., .., .. ., 2002 (10) 1339.

, 2

491

23. .., .., .. ., . , . . 1995


(11) 2236.
24. Fisher E., Steche A., Liebigs Ann. Chem. 1887 242 346.
25. .., .., .., .., . , . .
1996 (5) 1222.
26. Ukhin L.Yu., Orlova Zh.I., Mendeleev Commun. 1995 234.
27. .., .., . , 1962 (2) 342.
28. .., .., . , 1962 (7) 1290.
29. .., .., 1989 25 (12) 2594.
30. .., .., .. ., 1992 28 (3) 513.
31. .., .., .. ., . , . .
1991 (5) 1121.
32. .., .., .. ., . ,
. . 1991 (8) 1808.
33. Ukhin L.Yu., Morkovnik Z.S., Philipenko O.S., et al., Mendeleev Commun.
1997 153.
34. .., .., . , . . 1997 (7) 1336.
35. .., .., .., . , . ., .
36. .., .., .. ., . , . . 2002
(7) 1167.
37. .., .., .., ..,
1970 1313.
38. Paquette L.A., Stucki H., J. Org. Chem. 1966 31 1232.
39. Hensel S.R., Chem. Ber. 1965 98 1325.
40. .., .., .., .., . , . .
1999 (3) 566.
41. .., . , . ..,
.., .: -, 2001, . 2, . 314, . 450.
42. Birkofer L., Kim S.M., Engels H.D., Chem. Ber. 1962 95 1495.
43. .., , .: ,
1978, . 367.
44. .., .., .. ., . , . . 2000
(4) 729.

492

InterBioScreen

.., .., ..

470061, , . 40 , 1

l- d-- ,
, [1, 2].
, .
.

1,2- . , .. ,
, . , ()- ( -) 1
(S)- (2), (R)- 2
10%.

Ph

Ph

O
R

R
N

N
1

2
R = H, Me, Cl, NO2, CN, i-C5H11

, (-N, -NO2),
50 : 50, (S)-
(85%) [35].
()-,
(+)- (2S)-
[68]. (2) ,
, [9]. -,
, 2

493


: , (2R)- .
()- (+)-
[10].
()- - 3
(45%) 2,5--3,4- 4 (49%) ( 1).
1
Ph

HO

OH

OH

Ph

N
H

Ph
N

SO3Na

Ph

Ph

Ph
SO3Na
3

4 - .
HO

Ph
N
Ph
SO3Na
A

()- N - -, 100 (5 . .) 5 (92%)


[11] ( 2).
2

NC
Ph

+
N
H HCl

KCN

O
R

R = Ph, PhCH=CH

494

OH

N
H

HO
Ph

Ph

InterBioScreen


. [12]
()- (+)- ( 3). ,

3,4--5-() 6, 7. 6 7 ()-
(+)- ,

(2S,4S,5R)- (2S,4S,5S)-3,4--5--2-() [13].
3

R
Ph
N
H

OH

(-)-

Ph

ROH

MnO2

Ph
N
H

OH

(+)-

Ph

N
7

R = PhCCCH2

,- 8, 9, ..
( 4).
4

OH

Ph
N
H

OH

Ph
OH

O
H

()-
MnO2

OH

Ph
N
H

OH

(+)-

Ph

N
9

, 2

O
H

495

()- (+)-
,
10 [14] ( 5).
5
O
Ph

OH

Ph
OEt

N
H

OEt

N
10

2,3,4--5--2- 10
3--5- [14] ( 6).
6
O
Ph

O
NH2NH2H2O

OEt

Ph

OH

HN
N

N
H

10

, , , ,
[15, 16]. [17].
, N- ()- (+)- 11 7888% [18] ( 7).
7
Ph

O
N

OH

R'MgBr

Ph

R'
R

11
R = H, Ph; R' = CH2CH=CH2, CH2CCH, Bn, Et



496

InterBioScreen

. [19] 1,2- 13 N-Boc- 1,3-. N-Boc-2- 12, ,


( 8).
8

Ph

HO

R'MgX

Ph

HO

R'

HO

Boc

Boc

R'

12

13
R = Ph, Bu, Me; R' = CH=CH2, Et; X = Br, CI, I

[20]
. (2S,4S,5R)- (2S,4S,5S)-3,4-5--2- 14 15, ,
(2).

Mn(Co)3
H

Mn(Co)3
H

N
H

14

H
15


, , . [2123] , . ,

. , - -3,4-2--5,6- 16, 17 [2123] ( 9).
, 2

497

9
Ph

Ph

OH

Cl

Cl

16

N
H

Ph

17

()- 16, (+)- N,N'--(-----)-N,N'- 18 [24].

O
Ph

OH
N

Ph

OH

18

( ) (),
N-(2-) 19 -, - [25] ( 10).
10

Ph

Ph

OH
N
H

OH

O
N
H
19

()-
(+)-
[26].
N- 2- 20 7375% [27] ( 11).
498

InterBioScreen

11
Ph

Ph

OR
Cl

N
H

OR

OH

OH

Ph

N
20

()- (+)-

3- 21 [24, 28] ( 12).
12

O
Ph

OMe

ONa

Ph

OMe
N

NH

Cl

NH

Ph

21

-2- 20 23
N- ()- (+)- [24, 27, 28].
- 22 ( 13).
13
Ph

Ph

Ph

OH
CN

CN

N
22

20

Ph

OH

O
N

NH2
Ph

OH
N

+
H

Ph

OH

O
NH2

, 2

N
23

499

20 23 - 24 25 64 89% [24, 28].


Ph

Ph

OH
O

OH
O

OH

OH

24

25

20 23
26.
20 23 27
[29] ( 14).
14
Ph

RH

OH
O

N
Ph

R
26

O
H2N

OMe

Ph

OH
H
N

O
OMe

O
27
R = NH2NH, N

'

3,3-- 28 [11]. (3R)- ( 15).


15

Ph

O
N

LDA

R
H

Ph

O
N

R'Hal

Ph

R
OLi

O
N

R
R'

28
R = Ph, PhCH=CH; R' = H, Me, CH2CH=CH2, Bn, o-BrC6H4CH2

500

InterBioScreen

3- 29
2--4,5--6--2-(2-)-3- 30
[11, 30] ( 16).
16

O
Ph

O
N

Ph

Ph

O
NH

OH

Ph

29

Ph

OH

Ph

Ph

OR

Ph

O
30

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.

Spielman M.A., J. Am. Chem. Soc. 1944 66 1244.


Middleton W.J., Wedzger D., J. Heterocycl. Chem. 1979 7 1045.
Neelakantan L., J. Org. Chem. 1971 36 (16) 2256.
Agami C., Rizk T., J. Chem. Soc. Chem. Commun. 1983 1485.
Agami C., Rizk T., Tetrahedron 1985 41 (3) 537.
Neelakantan L., J. Org. Chem. 1971 36 (16) 2261.
Abdallah H., Gree R., Caree R., Tetrahedron Lett. 1982 23 503.
Wickstrom A., Wold J.K., Acta Chem. Scand. 1961 15 686.
Beckett A.H., Jones G.R., Tetrahedron 1977 33 3313.
Neelakantan L., J. Org. Chem. 1971 36 (16) 2253.
Chih-Jung Chang, Jim-Min Fang, Gene-Hsian Lee, Yu Wang, J. Chem. Soc. Perkin
Trans. 1 1994 3587.
.., .., .., .., 1997
67 (12) 2059.
.., . . - . , : - .
, 1998.
.., . . . . , : - .
, 1999.
.., .., .., .., 1996 66
(4) 696.

, 2

501

16. Tomas H.F., Hagorian L., J. Am. Chem. Soc. 1968 90 1007.
17. .., . . . . , : - .
, 1997.
18. .., .., .., 2000 70 (1) 164.
19. Agami C., Francois C., Tetrahedron Lett. 1994 35 (20) 3309.
20. .., .., .. .,
1992 5 (5) 1176.
21. .., .., .., .., 1997 67
(8) 2059.
22. Williams R.M., Im M.-N., Tetrahedron Lett. 1988 29 6075.
23. Williams R.M., Im M.-N., J. Am. Chem. Soc. 1991 113 9276.
24. .., . . . . , : - .
, 1999.
25. . ,
, . ., .., .: , 1985, . 9, . 575.
26. .., .., .., .
-2030: . .,
, 2001, . 365.
27. .., .., .. ., .
- , , 1998.
28. .., .., .. ., 1997 67 (7) 1222.
29. .., .., .. ., 1998 68 (8) 1320.
30. Agami C., Couty F., Prince B., Puchot C., Tetrahedron 1991 47 4343.

502

InterBioScreen

3-- 3-
.., ..
.
01033, , . , 64
,
[13], - ,
[4], [5, 6], - [7, 8] ,
[9]. , ,
[1012] . 3-(3-) ,
, 3-(4-) , 3- [4, 1320]
.

,
.
3- .
,
"" .

- -
--2- () .
, , ,
,
[3].
-
( 1) 3- 3-(2-)-5,7- 1 [21].
1

HO

OH

+
OH

CN

HCl

HO

OH
S

S
OH

, 2

503

O
HO

O
HO

OEt

OH
S

OH O

OH O
HO

O
S
OH

O
1

[22] ,
.
[23, 24]. [25] ,
-
.
2-
- [26]. [27],
--2- .
[28].
, ,
,
2-, [29].

, .
.. 28
915 ( 2)

3- [3074].
() 28 3- 915 [75] , . ,
2 ,
28
. , 12 26 .
. , 14 23 , 3- 12,
13 (58 ). ,
504

InterBioScreen

5, .

.

R
R'
R"

Het
R'''
28

R'

OH

R"

Het
R"'

915

2, 9: R = R'' = R'" = H, R' = OH; 3, 10: R = Me, R' = OH, R'' = R"' = H;
4, 11: R = R'' = H, R' = R'" = OH; 5, 12: R = R' = OH, R'' = R'" = H;
6, 13: R = R'' = H, R' = OH, R'" = Me; 7, 14: R = R'' = H, R' = Me, R'" = OH;
8, 15: R = R'" = H, R' = OH, R'' = Me
Het = 2-, 2-, 3- 5-,1,4--6-,
1,3--5-, 3,4--2-1,5--7-, -4-,
-4- -5-, 1--4-, -4-,
1--4-, 3-, 4--1,2,4--3-,
5--1,3,4--2-, 1- -2-, -2-,
-3-, -2-, -8-

1 13 6- 8-
. 15
, 14
, 10 5- 6-
- 8.5 . 5- 14 9, 11
. -
5-,
.
1 .
3-.
17
7- --2--4- 16 -
3540 ( 3).
, 2

505

MeO

OH

HCO2Me

MeO

O
O

OEt

16

OMe

17

16
.
[76], , 2-,
, [58, 63]
--2,4- 2
-
1%- 7--3- 9,
,
4-.
3-(4-) 11,
2, ( 4).
4

HO

OH

HCO2Me

HO

t-BuONa

S
O

4
HC(OEt)3
Py, Pip

HO

+
H

S
11

506

OH

+
H

18

HO

H2O

S
O
19

InterBioScreen

4 -
[25, 63] - 18 11 2- 19.
, 4 [27], , 11
. 3-(4-) [60, 64].
28 ,
(, ) 3- , 2 ( 5).
5
R
R

R5COCl

OH

Het

(R5CO)2O

Et3N

Het
R

20

28
R5 = Me, CF3, CO2Et

[77, 78] 2- . ,
(, N-) [79].
2- ,
.
,
--2,4-
, [79].
,
2,4- 90100
2030 .

2-.
. ,
2--3-. ,
-(2-)-, -(2-)-,
-(2-)- -(2-)-2,4- , 2

507

2-3--7-,
--2,4- [79]
140160 ,
, . -(1-)2- 3-(1-) 21 [20].
3-(1--5) 21
3-(2--1,3,4--5) 22 [14].

O
R

N
O
21

N N

O
O

R = H, ,

22

N N

2- [80].
,
[81],
.
. 2
2- [82].
--2,4- 28
, 0, , 2--3- 20.
-(2-)- -(2-) 23
-
12-[3',2'-3,4][1,2-a]-12- [83] 12--[2,3-c]-12- 24 [84] ( 6).
6
O
Hal

RO

OH

R'"

N
O
23

Cl

RO

R'
R"

R'"
R'
R"

O
24

R = H, Me, Pr, COMe; R' = R'' = H, R'+R'' = CH=CHCH=CH; R''' = H, Me;


Hal = Cl, Br

508

InterBioScreen

[85], 2-
[78] [79]
,
2 .
2-, - (, NO2, SO2CH3, SOCH3, COCH3). , ,
- 2- .
[86, 87] 28, -
,
: -(2-), -(2-), -(4--2-),
-(4--1,2,4--3-), -(4-)--(4-), -(4-), -(2--4-), -, -(2-), -(5-2-), -(4-) -(3,4-),
.
, 5,7-, ,

[86]. 2 5,7- , --2,4,6-, 2--5,7- [81].
.
25,
2- N- [88] ( 7).
7

H
N

HO

OH

HO

+
Ar
R

Ar
R

O
25

, , . 6575%.
, 2

509

26 -,
2- [89]
( 8).
8
N

OH

BF3

Ar

OH
Ar

N
O

NH
R

OH
Ar

N
R

NH

Ar
O

26


[90].
2-
[91, 92] ( 9).
9
OH

OH
Ar

HCN

Ar

OH

NH2

HCl

OH

NH3
Ar

O
+
NH4

Ar
O
26

28 30
27 29 - [93, 94] 1,2- ( 10).
510

InterBioScreen

10
Het

OH

OMe

Het

27

28
N

Het =

N
H

N
S

Me

OAc

Cl

R
O

O
29

NH2

30

R = H, Cl, Br, OMe

.. 7- 3- 32 31
. [56, 7173] ( 11).
11

Ph

Ph
MeO

H2O2 MeO

MeO

O
Het

Het

Het

31

O
32

3-,
--2-,
, , ,
. 3-
.
3-,
.
, 2

511

1963 [95]
,
34, 35, 33, 36 5 7
.

HO

O
N
+

O
34

33

HO

35

36

3- 37 38 [9699] ( 12).
12

R'

HN

R'

R
N

Cl
O

37

38

R = H, Me; R' = H, Me, Oe;


X = O, CH2

3- 39 2,3--2-(1-)-3-, 2-(1-) 40 [100] ( 13).


13
H
N

Br
O
39

512

N
Br

HBr

O
40

InterBioScreen


. 3- 41,
42 -3- . 3-(1--5) 43 [4, 14, 15],
.
O

O
R

O
O

R
O

41

HN N

43

42

[101] 3- 44 3- 41 - ( 14).
14

RNHOHHCl

R'
N
O

O
O

R"

44

41
R' = Me, Ph; R" = CN, Ph

-3- 41
45 [102] 63%.
3-, 1 : 2 : 4
[102, 103] ( 15).
15
O
O

R
O

Ph

Ph

HN

NH

NH
N

R
O

OH

Ph
Ph

41

, 2

513

NH2
N

R
O

OH

Ph

H
N

R
O

Ph

Ph

N
Ph

45

- 3-

3-(-2-) 46 [104] ( 16).
16

O
O
O

NH2

NH2

N
H

46

3- 47 3-(1-)-2- 48 [80] ( 17).


17

Ph

Ph

N
N
N N

47

48

NH2

NaN3
HC(OEt)3

1.
2.
3.
4.
5.
6.
514

Middleton E., Kandaswami C., Theoharides T.C., Pharmacol. Rev. 2000 52


(4) 673.
Mongelli N., .., .., .., .
, . ., .: , 1968, . 355.
.., .., .., .,
, - , 1985.
Nohara A., Ishiguro ., Kuriki H., et al., J. Med. Chem. 1977 20 141.
Cozzi P., Branzoli U., Lovisolo P., et al., J. Med. Chem. 1986 29 404.
.., .., .. ., .-. . 1981 15
(11) 40.
InterBioScreen

7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.

Cozzi P., Branzoli U., Mongelli N., et al., Fr. Patent 2 477 545; Chem. Abstr. 1982
96 122508.
Cozzi P., Pillan A., Lovisolo P., Belg. Patent 893 917; Chem. Abstr. 1983 99 5629.
Kapoor R.P., Sharma V.P., Singh Om.V., Garg C.P., Indian J. Chem., Sect. B 1991
30 1152.
Dutch Patent 70 267; Chem. Abstr. 1953 47 6445h.
Wander A., GB Patent 728 767; Chem. Abstr. 1956 50 7876i.
Schmutz J., Hirt R., Kzle F., et al., Helv. Chim. Acta 1953 36 (3) 620.
., ., ., 51-18 955; . 1977
8113.
Nohara A., Ishiguro ., Kuriki H., Sanno Y., 1 540 391; .
1979 18178.
Strandtmann M., Cohen M.P., Klutchko S., Shavel J., 4 116 971;
. 1979 7178.
Kato T., Nohara A., Kavarasaki T., Sanno Y., J. Takeda Res. Lab. 1980 37
(3/4) 195.
Strandtmann M., Cohen M.P., Klutchko S., Shavel J., Ger. Patent 2 840 930;
Chem. Abstr. 1980 93 46687.
Nohara A., Umetahi T., Sanno Y., 4 151 180; . 1979
21140.
Strandtmann M., Cohen M.P., Klutchko S., Shavel J., 7 827 407;
. 1981 989.
., ., ., C ., 53-116 376;
. 1979 15173.
Gronowitz S., Ekman R., Arkiv Kemi 1960 17 (9) 93; Chem. Abstr. 1961 55 27294f.
Spath E., Lederer E., Ber. 1930 63 743.
Mahal H.S., Rai H.S., Venkataraman K., J. Chem. Soc. 1934 1120.
Joshi P.C., Venkataraman K., J. Chem. Soc. 1934 513.
Szabo V., Borbely Sz., Farkas ., Tolnai S., Magy. m. Foly. 1975 81
(5) 220.
Szabo V., Borbely Sz., Magy. m. Foly. 1976 82 (6) 259.
Sethe V.R., Venkataraman K., Curr. Sci. 1949 18 373.
Szantho V., Farkas L., Acta Chim. Acad. Sci. Hung. 1959 19 (23) 217.
Karmarkar S.S., J. Sci. Ind. Res. 1961 20 (7) 334.
.., ., .. ., 1973 9 (12) 2561.
.., .., ., 1972 (10) 1317.
.., .., .. ., 1973 (9) 1202.
.., .., .., .., . . .
1978 44 (10) 1081.
.., .., .., ., 1972 8 (5) 1085.
.., .., .., ., 1972 (10) 1324.
.., .., .., , . 1977 (6) 528.
Moldenhauer O., Trautmann G., Pfluger R., Dser H., Liebigs Ann. Chem. 1953
580 176.
Gaertner R., J. Am. Chem. Soc. 1951 73 4400.
Weinstein B., Craig Al.R., J. Org. Chem. 1976 41 (5) 875.
Sasamoto M., Chem. Pharm. Bull. 1960 30 (8) 324.

, 2

515

41. .., .., .., .-. . 1976 10 (8) 74.


42. .., .., .., .., ,
C. 1980 (5) 61.
43. .., .., .., ., 1973 9 (12) 2572.
44. .., .., .., .., ,
C. 1978 (7) 623.
45. .., .., .., , C. 1978 (3) 257.
46. .., .., .., 1975 (12) 1593.
47. .., .., .. ., 1977 (9) 1180.
48. .., .., , . 1979 (2) 119.
49. .., .., , . 1978 (3) 236.
50. .., .., .., .., . .
. 1978 44 (3) 265.
51. .., .., .., 1979 (1) 25.
52. .., .., .., 1980 (7) 892.
53. B.., .., .. ., .-. . 1981 15
(11) 40.
54. .., .., .., 1976 (8) 1108.
55. .., .., .., 1974 10 (6) 1277.
56. .., .., A.., .., . . .
1982 48 (7) 765.
57. M.., .., .., 1973 9 (12) 2568.
58. ., .., ., .., 1975 (2) 174.
59. .., .., .. ., .-. . 1980 14 (1) 24.
60. .., ., .. ., 1975 (8) 1030.
61. .., .., .. ., 1982 (3) 321.
62. .., .., .., . . . 1980 46 (9) 948.
63. Szabo V., Borbely Sz., Grishko L.G., Chilya V.P., Magy. m. Foly. 1976 82
(6) 263.
64. Szabo V., Chilya V.P., Grishko L.G., Babichev F.S., Magy. m. Foly. 1977 83
(6) 274.
65. .., .., .., .., ,
. 1981 (5) 60.
66. .., .., ., 1972 (10) 1321.
67. B.., .., .., 1975 (8) 1146.
68. .., .., .., 1976 (11) 1474.
69. .., .., .., , . 1978 (6) 518.
70. .., .., .., .., , .
1980 (4) 57.
71. .., A.., .., .., 1981 (9) 1202.
72. .., .., .., .., . . . 1983
49 (2) 174.
73. Grishko L., Turov A., Khilya V., et al., Acta Chim. Hung. 1983 112 (4) 401.
74. Litkei Gy., Patonay T., Bognar R., et al., Pharmazie 1984 39 (11) 741.
75. Sethe V.R., Venkataraman K., Curr. Sci. 1949 18 373.
76. Ollis W.D., in The Chemistry of Flavonoids Compounds, Geissman T.A., Ed.,
New York: Pergamon Press, 1962, p. 385.
516

InterBioScreen

77.
78.
79.
80.
81.
82.
83.
84.
85.
86.
87.
88.
89.
90.
91.
92.
93.
94.

Allan J., Robinson R., J. Chem. Soc. 1924 2192.


Baker W., Robinson R., J. Chem. Soc. 1925 1981.
Szabo V., Farkas E., Levai A., Acta Phys.-Chim. Debrecina 196970 15/16 191.
Baker W., Chadderton J., Harborne J.B., Ollis W.D., J. Chem. Soc. 1953 (6) 1852.
Baker W., Harborne J.B., Ollis W.D., J. Chem. Soc. 1953 (6) 1860.
Farooq M.O., RahmanW., Ilyas M., Jehan S., Chem. Ber. 1961 94 (8) 1996.
.., .., , C. 1981 (6) 66.
.., .., , C. 1981 (7) 46.
Bechet G.J.D., Ellis G.P., Tetrahedron Lett. 1976 (9) 719.
.., .., .., , C. 1985 (4) 59.
.., .., , C. 1985 (7) 44.
Krishnamurty H.G., Prasad J.S., Tetrahedron Lett. 1977 35 3071.
Kabbe H.J., Widdig A., Angew. Chem. 1982 94 245.
Fukui K., Nakayama M., Bull. Chem. Soc. Jpn. 1965 38 1803.
Farkas L., Ber. 1957 90 2940.
Kawase Y., Sekiba T., Fukui K., Bull. Chem. Soc. Jpn. 1958 31 997.
.., .., .., . . . 1983 49 1202.
.., .., .., . . 883 040;
Chem. Abstr. 1982 96 181148.
95. William W., Bencze L., Belg. Patent 633 436; Chem. Abstr. 1964 61 1840.
96. Winter C.W., Hamilton C.S., J. Am. Chem. Soc. 1952 74 3999.
97. Colonge J., Guyot A., Bull. Soc. Chim. Fr. 1958 (3) 329.
98. Rastagi M.K., Chaudhary K., Kapoor R.P., Garge C.P., Indian J. Chem., Sect. B
1979 17 (1) 34.
99. Rastagi M.K., Chaudhary K., Kapoor R.P., Garge C.P., Indian J. Chem., Sect. B
1978 16 (10) 895.
100. Cozzi P., Pillan A., J. Heterocycl. Chem. 1985 22 441.
101. Baruah A.K., Prajapati D., Sandhu J.S., J. Chem. Soc. Perkin Trans. 1 1987
(9) 1995.
102. Ghosh C.K., Sinha Roy D.K., Indian J. Chem., Sect. B 1978 16 (8) 727.
103. Ghosh C.K., Mitra A.K., Parta A., J. Indian. Chem. Soc. 1980 57 450.
104. .., .., 1999 (1) 3.

, 2

517

:
.., .., ..
.
01033, , . , 64

2--1--2-
( , , ), .
(), .
, , , . .
5

4
3

6
7
8


.

.
3-
, ,
, : 1) ""
; 2)
.
,
, ,
.
(
) , , , 3- 1,
Het = 2- [1, 2], 2- [3], 3- 4- [1], 2-
518

InterBioScreen

[46], 4- [4], 1,2,4--1-


[7], 1,2,4--3- [8], 1,3,4--2- [9, 10], 1,3,4--2- [11],
-2- [12, 13], N--2- [14], -2-
-2- [2], 2--4- [15], -3-
[16]. 2- 2, :
( 1).
1
Het
N

O
H

Het

NH
HCl

OEt

OH

Het

Het
R
1

[17], (3f, i, j;
4aj; 5f; 6f; 7fh; 8f; 9b, c, fj; 10c, fj; 11fj; 12b, c, fj) .
Het
R
O

3f, i, j; 4j; 5f; 6f; 7fh; 8f; 9b, c, fj; 10c, fj; 11fj; 12b, c ,fj
3 R = H; 4 R = 7-OH; 5 R = 8-OH; 6 R = 7,8-(OH)2; 7 R = 8-OMe;
8 R = 8-OEt; 9 R = 6-NO2; 10 R = 6-Cl; 11 R = 6,8-Cl2; 12 R = 6-Br;
a Het = 4--2-; b Het = 4-(4-)-2-;
c Het = 4-(3-)-2-; d Het = 4-(3,4-)-2-;
e Het = 2,4--5-; f Het = -2-; g Het = -2-;
h Het = N--2-; i Het = 2-; j Het = 2-

HetCH2CN
3-. 96% , 4bd,
9b, c, 10c, 12b, c - i-PrOH.
.
4- ZnCl2
, 2

519

14,
ZnCl2 [18] ( 2).
2
Het

CN

Het
H

OH

ZnCl2

CHCl3

Het

ZnCl2

OH

14
Het = -2-, 5--2-


15
4090% 3- [19]
( 3).
3
H
N

O
NO2

OR

Het

H
N

Het

R
O

N
Het

OH

HCl

15

[7] 4- (1,2,4--1-)- (-1-) , (12 )


, 1-(-3-).
- 4--3-(2-) 16 [20, 21] ( 4).
4
OEt
Het

O EtO

O t-BuONa
R

520

OH

Het

OH

O
OEt

Het
O

OH

InterBioScreen

OH
Het
R

16

Het = 5--2-, 2-

.
3-() 17,
, CSNH2,
3-(2-X--4-) 18, X = CH2CN,
, 2,4-(-3-) [22] ( 5).
5
S

O
Br

R
O

H2 N

17

18

R = H, 5,6-, 7-Et2N;
X = NH2, NHNH2, CSNMe2, CH2CN, N(CH2)4, Ph, 4-MeC6H4,
3,4-MeOC6H3, 4-(Me2N)C6H4, 4-ClC6H4, 4-[N(CH2)4]C6H4

3-(-4-)
[4, 2328].
17 Me2N-CS-X
Mg(ClO4)2
5-(-3-) 19 [22] ( 6).
6

S
S
17

Mg(ClO4)2

R
O

O ClO4

19
R = H, 5,6-, 7-Et2N; X = Me2N, Ar

3-(-3-) 17
[29].
, 2

521

3-(R-)
Ar-C=N-NH-CS-NH2
3-(2--4-) 20, 3-(R-) 3-(1,3,4--5-) 21 [30]
( 7).
7

Ar

Ar
N N

N N
OH N
S
HN
N

NH2

20
S

OH

HN
N
NH2

Br
O

S
R

Ar

OH

OH HN

NH2

N
S

21

3-()
3-(-3-)[f][3,2-b] 22 [31, 32] 3--7-(3-)[3,2-b]-1,2,4- 23 [31] ( 8).
8
H
N
R'

H
N

SH

R'

N
R'

O
R

Br

HS

Ar

N N
H

R
Ar

N N
N

R=

22

S
23

O
O
R' = H, 5-Cl, 5-Me, 5,6-Me

3-() 17 2--1,3,4 4--5--s- 6-(-3-)522

InterBioScreen

[2,1-b]-1,3,4- 6-(-3-)-7-1,2,4-[3,4-b]-1,3,4 [33].


3- 3-; 3-(2-4-) 24, ZnCl2
3-(-2-) 25 [34] ( 9).
9
NH
H 2N

2HBr
NH2

NH

NH2

N
R

S
24

PhNHNH2

R
N
H

R=
O

25

3-(-4-) 3-
N- ; Br2 (a LaIII
SmIII) [35, 36]; [33].
3--4,7-
3--4,7-,
3- [37] ( 10).
10
O2N

H2N
N
H

NO2

O2 N

NO2

N
26

R
O

AcOEt
EtONa

NH2OHHCl

O
NH2
NH2

OH
R=
HO

O
N

27

R
N
N

28

, 2

R
523

3-(4,7--3-)-1-(2,4-)-5- 26
3-(4,7--3-)-5- 27
, 28
.
3- - HClO4 ( 1 : 1)
2-(-3-) 29 [38]. 2 : 1
( 11).
11

R'

O
O

OH

HClO4

OEt

R'

R
O

O 29 ClO4

R, R' = H, 5,6-, OH, OAlk, Alk2N

3-
4-(-3-)-1,2,3- [39]. 3-
2--4-(-3-)-3- [40].
( 3-
) 1-()
2-(3-) [41].
3-()

3-(2-) [42].
3-- 3- -2
HOCH2CH(OH)R (R = H, Me) 3-(4-R-1,3--2-) [43].
4--3- -
2-(-3-) 30 [44] ( 12).
12

Ar
OH

OH

O
H

O
524

Ar

Ar
O

AcOH

Ar
N
H

NH4OAc

30

InterBioScreen

3 3- 31 [10], 32
[45], 33 [f] [4648] ( 13).
13
OH

N N

O N2H4HCl

2
Et2N

Et2N

31

NEt2

O N

NOH
Ph

Cl
O

O
[10]

AlkO

NH2

AlkO

Ph

32

[45]

NH2

NH2

OEt

33

N
H

O
[4648]

3- 4-R-2-(-3-) 34 [46] ( 14).


14
S
NH2

R
O

R'

R'
N

R
Br

34
R = H, 7-OH, Alk, OAlk, 7-Et2N, 5,6-;
R' = H, Alk, Ph, Bn, PhS, 4-PhC6H4, CO2R, CONH2;
Y = O, NH

, 2

525

.
, ,

HBr.
3- , , 3- [49].
3- 3-(-3-)-3--2- 35 3-(3-)-3- 35b ( ,
3- POCl3 . HClO4; , HClO4 [50])
( 15).
15

Cl

HClO4

N ClO4

Cl

35a

Cl
N

H2O

Cl
H

35b

R = R'
O
O
R' = H, 5,6-, 6-Br, 7-OH, 7-OMe, 7-Alk2N

35 35b , 5-(-3-)-5-
R4NHCS2 HClO4 -3- 36, 37,
38 - 39 [50] ( 16).
16
Y

CS2, R4NH2
35a

35b

Y
CN

Cl

HClO4

38

Y
CN

R2R3NH

ClO4

R2
N

NH2
Y
CN

R
526

InterBioScreen


HO

Y
+

O
NH2

ClO4

R
HClO4

Y
O

39

36

R3 = H

N
R

ClO4

NH2
37

R = R'
O
O
R1 = H, 5,6-, 6-Br, 7-OH, 7-OMe, 7-Alk2N;
R2, R3, R4 = H, Alk;
Y = CN, CO2Et, 2-

35 35b 5-(-3-) 40 [50, 51], 41 [38], HClO4 42,


43 [50]
( 17).
17
NH2NH2

40

35a

35b

N
H

OH
R

O
41

ClO4

H 2N

N
4
R

HClO4

N
R

S
N

4
ClO4 R

NC

CN

N
NH2

42

CN
43

R= R

O
O
R1 = H, 5,6-, 6-Br, 7-OH, 7-OMe, 7-Alk2N;
R2 = H, 7-OH, 8-OH, 8-OMe, 7-Alk2N;
R3 , R4 = Alk

, 2

527

44 45 [45], 44 P2S5 46 [11] ( 18).


18

R'

H
N

N N

P2S5

N
H

AlkO

R'

N N

44

45
R' = Ph

R=

R'

46
R' = Ph, Pr, 4-

3-(), 3-()
, - 1--2-4-(-3-) 47,
HClO4 2--3--5-(-3-) 48 [22] ( 19).
19

ClO4

Ph
N
+

R 48

Ac2O
HClO4

SCN

R
HN

Ph

Ph
N

SH

N
R 47

R=
O

NaN3 3--4-, 3--5-(4--3-) [52].


3-(-) ( 2, 3 ) 2--2--3-(-3-)- [53].
2--3-
2-N- [54],
, 2-N-R- 3- [12, 15, 16, 55] ( 20).
528

InterBioScreen

20

O
N

NH2
R"

NH3

R"

XH
HX
NH2

R"
O

NH2

O O
S
HN

NH2

NH2

SO2NH2

NH

O
NH2
O
Y

Ac2O

O
N
O

N
AcOH

HN

R = R'

N
R
O
O
R' = H, 5,6-, 6-Br, 7-OH, 7-OMe, 7-Alk2N; R" = H, Cl;
X = NH, O, S; Y = CO2H, CONH2

N(1)- -3- 49 ( 2--3- )


50, 51 52 [9] ( 21).
21

p-

N N
R

N N

AcOH

N
HN
49

Ph

50

NH2
R

N
H

Ph
O

O
O
R' = H, 6-OMe, 7-Alk2N

Ph

N N

P2S5

R
R = R'

51

Ph

52

, 2

529

, 2--3-
, 2-N-)-3-. 2-(-3-)-1,3,4-
[56].
3-
7--3--4- , .
2-(-3-)-1-, 3-(2-)-, 3-(2-)-,
3-(2-), 2-, 3- 4-(-3-), 3-(-3-), 2-(-3-) - [57]. 4-
N--2-(4--3--1,2--2- 53 [58].
OAc

53

N
Ac

FeCl3 3,3'- [59]. 3 (2-, 2- 3-


1,3-) [60]. 3-
[61].
4-

3-.
, , ,
, .
4- ,
4- 54 [62] ( 22).
O
O

OEt

54

530

R = Me, 4-MeOC6H4

OEt

Ph3P

N
O
H
N

22
O
OEt

55

InterBioScreen

()-3-(-4-),
54 (), 5-(-4-)-3--4,5-4- 55 (R = Me) 4-(4-)-3--4,5--5-,
4- 55 (R = 4-MeOC6H4).
4-() - 4- 5-(-4-)3-R-4--4,5--1,2,4- (R = CH3, 4-CH3OC4H6).
(20%) , 4-
-, 4- 5-(-4-)-3-(4-)-1,2,4- [62].
1,3- -4- , - - (-4-)
1,2,4-, - -
[63].
N-(3--4-)-2,5- 56
3--4- [64] ( 23).
23

H
N
NH2

Cl
NO2
O

HN

H
N

NH

O
NO2 H O
2

NO2
56

4-([b]-2-)
4- - [65].
, ,

, , , 1-(-7-) [66];
. , - R-CO-CH=NOH
4-(7--3-)-1,2,3- Ac2O
3,7-(1,2,3--4-) [67]. 3-(1,2,4-1-)-7-(1,2,3--2-) 1-(-3-)1,2,4- : , SnCl2,
- [7].
, 2

531


1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
532

Wolfbeis O.S., Marhold H., Chem. Ber. 1985 118 3664.


Wolfbeis O.S., Koller E., Hochmuth P., Bull. Chem. Soc. Jpn. 1985 58 (2) 731.
Mohareb R.M., Ibrahim N.S., J. Prakt. Chem. 1989 331 (3) 387.
.., .., .., .., 1997
(10) 1417.
Vamvakaris C., Patsch M., Mach W., Ger. Offen 2 807 761; Chem. Abstr. 1980
92 41931x.
.., . . . . , , 1998.
Dorlars A., Schellhammer C.W., Wirth W.D., US Patent 4 005 098; Chem. Abstr.
1977 86 122955m.
Kazmierkiewicz W., Liebigs Ann. Chem. 1987 (6) 541.
.., .., .. ., 1996 (2) 186.
Schwander H., Ger. Offen 2 319 230; Chem. Abstr. 1974 80 134931q.
Patsch M., Vamvakaris C., Ger. Offen 2 529 434; Chem. Abstr. 1977 86 122953j.
.., .., .. ., 1998 (12) 1664.
.., .., .. ., 1995 65 (9) 1547.
.., .., .. ., . . . .
1999 454, 4 (27) 146.
.., .., .., .., 2000 (9) 1175.
.., .., .. ., 1998 (7) 916.
.., .., .., .., 2001 (8) 1120.
Srinivas K., Krishna K.L., Indian J. Chem., Sect. B 1998 37 963.
Czerney P., Hartman H., J. Prakt. Chem. 1981 324 (1) 21.
.., .., .., .., . . .
1998 (1) 45.
., .., ., .., 1975 (2) 174.
Czerney P., Hartman H., J. Prakt. Chem. 1983 325 (4) 551.
.., .., .. ., . . 1991 (4) 48.
.., .., ..., .., 1997
395, 2 (25) 264.
Bilokin Y.V., Gella I.M., Heterocycl. Commun. 1998 4 (4) 339.
Srimanth K., Rao V.R., Indian J. Chem., Sect. B 1999 38 (4) 473.
Lacan M., Cacic M., Vekic L., Kokic C., Bull. Soc. Chim. Belg. 1980 45 (78) 267.
.., .., .. ., . . . .
., , 1991, . 127.
Ebrahim A.E.F., Al-Azhar Bull. Sci. 1996 7 (2) 1173.
Djudjuc R., Trkovnik M., Kitan D., Org. Prep. Proced. Int. 1985 17 (3) 206.
Kulkarni M.V., Patil V.D., Biradar V.N., Nanjappa S., Arch. Pharm. 1981 314
(5) 435.
Cisowski W., Herba Polonia 1983 29 (34) 301.
Rao V.R., Rao M.S., Rao T.V.P., Collect. Czech. Chem. Commun. 1986 64
(10) 2214.
Rao L., Mukerjea A.K., Indian J. Chem., Sect. B 1994 37 (2) 166.
Vardhan V.A., Rao V.R., Indian J. Chem., Sect. B 1997 36 (12) 1085.
Vardhan V.A., Kumar V.R., Rao V.R., Indian J. Chem., Sect. B 1999 38 (1) 18.
InterBioScreen

37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
59.
60.
61.
62.
63.
64.
65.
66.
67.

Lacan M., Cacic M., Cizmar V., Babic M., Bull. Soc. Chim. Belg. 1981 46 (10) 531.
Czerney P., Hartman H., J. Prakt. Chem. 1983 325 (3) 505.
Kumar V.R., Rao V.R., Phosphorus, Sulfur, Silicon Relat. Elem. 1997 130 185.
Yagodinets P.I., Russ. J. Gen. Chem. 1998 68 (8) 1249.
Brahmbhatt D.I., Raolji G.B., Pandya S.U., Pandya U.R., Indian J. Chem., Sect. B
1999 38 (2) 212.
Sabnis R.W., Rangnekar D.W., Sonawane N.D., J. Heterocycl. Chem. 1999 36
(2) 333.
.., .., .., .., . . .
1994 47 (1) 102.
Bobarevic B., Trkovnik M., Monatsh. Chem. 1972 103 (4) 1064.
Davidson H., Johnson K.T., Leggeter B.E., Moore A.J., Ger. Offen 2 344 834;
Chem. Abstr. 1974 81 38958d.
Abdou S., Fahmy S.M., Khader M.M., Elnagdi M.H., Monatsh. Chem. 1982
113 985.
Brown H.D., US Patent 3 338 784; Chem. Abstr. 1968 68 78284u.
Sarpeshkar A.M., Rajagopal S., Indian J. Chem., Sect. B 1975 13 1368.
Westphai G., Tetrahedron 1969 25 5199.
Czerney P., Hartman H., J. Prakt. Chem. 1982 324 (2) 255.
El-Deen I.M., Chin. J. Chem. 1999 17 (4) 391.
Krstic L., Solujic S., Sukdolak S., et al., J. Serb. Chem. Soc. 1998 63 (11) 841.
Abd El-Gawad I.I., Harhash A.H., Khalil A.M., Tawfik N.I., The Indian Textile
Journal 1981 91 (August) 105.
.., .., .., .., 1994 (6) 760.
.., . . . . , , 1997.
.., .., .. ., 1999 (2) 190.
.., .., .., .., 1990
(12) 1600.
Ahluwalia V.K., Kumar D., Mehta S., Heterocycles 1979 12 (2) 259.
Reisch J., Zappel J., J. Heterocycl. Chem. 1992 29 1035.
Vernin G., Coen S., Metzger J., Parkanyi C., J. Heterocycl. Chem. 1979 16 97.
Tabakovic I., Trkovnik M., Batusik K., Tabakovic K., Synthesis 1979 590.
Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., Hadjipavlou-Litina D.J.,
J. Heterocycl. Chem. 1996 33 967.
Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., et al., J. Heterocycl. Chem. 1998
35 619.
Tabakovic K., Tabakovic I., Trkovnik M., Trinajstic N., Liebigs Ann. Chem. 1983
(11) 1901.
Khan I.A., Kulkarni M.V., Indian J. Chem., Sect. B 1999 38 491.
Ohkubo J., Tsujimoto M., Tsukahara R., Jpn. Patent 73 17 626; Chem. Abstr. 1974
80 134943v.
Hans S., Ger. Offen 2 355 116; Chem. Abstr. 1974 81 171366a.

, 2

533


2--4-
.., a ..
. ..
119991, , ., 47
2--4-
.
[16], ,
.
1. 2--4-
4- , ,
, 1,3- , 1,3-
.
1.1 1,3-

() 1,3- () [718]. , , () 2,3- . 1,3-


, , , , , 3-(2-)-1,1,1- .
, .
, , , , NaOEt.
, () [19].
-, 1,3- 1 2.
3,
4, 5. 5 6, 7 4- 8 ( 1).
1
Ar

R'

R'
O
O
R"
534

+
B

O
R"

NC

Ar
X

R'

R"

CN

InterBioScreen

Ar

R'

R"

Ar

R'

CN

R"

Ar

Ar

R'
O

R"

R'
O

R"

NH

NH2

R' = Me, OEt, Ph, 2-C4H3S; R" = Me, Ph; X = CN, CO2Et

1,1,1--3-(2-)
[18, 20].
1,1--4--4-(2'-)-2-, 6-(2'-)-4--3--2(1),
.
9 ( 2). , ,
2--4- 10.
48 , 4- 10.
3,3--1,1,2,2 11 12, b [21].
2,3- 9b
, 10.
, , - [15, 22].
2

O NC R
O
O
1a

CN

+
R

CN

NH2

NC
NC
NC
NC

9a, b
10
11
R = CN (9a, 10), CO2Et (9b); Ar = Ph (12a), 4-MeC6H4 (12b)

O
O

Ar3P
12a, b

5-- 5- (, ,
, 2

535

.), , N,N- 5--2-(2',2'-),



[7].
-3-
() [11] 1,3-
. , , c 2--4-.
3--4--1-, , ,
[23, 24]. , ,
,
[25]

, 4-, [26].
2-
, , , [27].
2--5--4-
- [28].
, 1,4- , , .
-
.
-, , -,
.
1.2 , ,
,-
2--4-
, , ,- - .
[13] - 13e ( 3), .
4-
14 1,3- 15.
13 . 13e 16e
.
536

InterBioScreen

- 16
2--4- 14 (8%), 17,
16 , .
3
Ph

NC
O

H2N

O
NH
R

Ph

14a

17a

NH
R

1
CH2(CN)2 30

Ph

CN

NH
R

13ae
O

NC

O
NH
R

Ph

2
CH2(CN)2 30

NC
NC

Ph

O
NH
R

H2N

Ph

NH
R

CN
16ae

15be

17be

R = Bu (a), Pr (b), i-Bu (c), C5H9 (d), C6H11 (e)

14
- 16e
. 15be (2231%),
17be (911%), 16be.
4- , ( 4) [1416, 2934]
18 19
().
4
R

R'
O

O
R"
19

R'

N
H2N

R"

18

R = Alk, OAlk, Ar, Het; R' = COMe, CO2Alk, CN; R" = H, Cl, Alk, Ar; X = CO2Et, CN

, 2

537

2--5--3--4- 2--3,5--4- [35].


, 1,4- 1,2- [36],
2-.
19 21 22 20 [9]
( 5).
5
R"'
N
21

R'
O

R'"

H2N

R"

H2N

R"'

R'
O

R"

22

19
20
R = Alk, Ph, CO2Alk, CO2CnH(2n-2); R' = Alk, OAlk, CO2Alk, CO2CnH(2n-2), Hal, Ar,
Py, C4H3SO, CF3, NO2, CN; R" = Alk, OAlk, CO2Alk, CO2CnH(2n-2), CO2CnH(2n-4);
R"' = H, Alk

3-- 23 3--2,4- 23b


[37]. 2-4--5--3-, 3- 2--4--5--3- 24, 3-
2--4,4,5--3--6--4- 25 ( 6).
6

O
X = Cl
23a

O
X

NH2
O

CN

24

O O
O O

OEt

X = Br

23b

O O
26

538

OEt

O
23a, b

OEt

OEt

O
NH2

25

InterBioScreen

, 26 .
2--4- 27
( 7) [38].

7
Ph

NC

R*

Ph

NC

CN

R*
O

H2N

28ac

27ac
CN

NC

O
Ph

R*
O
29ac

O
R* =

O
(a),

(b),

OEt (c)
H

A
- 28c ( ) ,
B -
29c ( ). 27c
( A 93, 94 93% ; B
(Z)- 29, (Z)- 29b 29c-(Z/E, 75 : 25) 52, 59 85%, ), ,
1 : 10.
2- ( 8) [39, 40],
,- 30d, - , 2--4- 31d,
30e , 2- 32.
30d .
, 2

539

8
CN
CN

Ph
S

Ph
S

X = Ar

CN
O

NH2

31ad

Ar

30ad

CN

Ph
S

X = NMe2

Y
N
H

32a, b
X = Ph (a), 4-MeOC6H4 (b), 4-NO2C6H4 (c), 4-Py (d), Me2N (e);
Y = CN (a), CO2Et (b)

1.3 2--4-
2--4- .
- . , N--
N- 33
34 [41, 42] ( 9),
.
.
9

Ar
Ar

O
Az

Az

CN

+
NC

CN

NH2

34

33

N
N
N
N
N
N
HN
N;
N;
N ;
Az = N N ; 2
;
N N
N
N
N
N
N
NO2
NO2
NO2

Ar = Ph, 3-IC6H4, 4F-C6H4, 2-C4H3S; R = Me, Ph

- 35d ( 10), (36d, 1252%) [43].


540

InterBioScreen

10
CN

O
NC

NC
NC

EtOH
H2O

CN

R
CN
O

NH2

36ad

35ad

R = Ph (a), 4-MeC6H4 (b), 4-ClC6H4 (c), 4-BrC6H4 (d)

2--4- (3, Ar = 2-C4H3O, Z = CN, COOEt)


[44].
( 11)
[45] 5--4-[2,3] 37, b, 38, b 2--4 39, b 38 : 39 3.3 : 1 38b : 39b 2 : 1 5--4-[2,3]
37. 5--4-[2,3] 37b
2--4 39c, d (58%
64%, ).
11
O

R R'

CN

O
37a, b

R'

NaH

+
O

NH2

HO

39ad

38a, b

R = H (37a; 39a, b), Me (37b; 39c, d); R' = CO2Et (37a; 39a, b), PO(OMe)2 (37b; 39c, d);
X = CO2Et (38a; 39a, c), CN (38b; 39b, d)

(,
) 2--4 [46].
2--4 40c, 2,4--1,3- 41 35ac, e, f [47, 48] ( 12).
12
R

CN

R'
CN

NC

41

SH
K2CO3

NC
R'

R
O

CN

NC
R'

35ac, e, f

R
O

NH2

40

R = CO2Me, CO2Et, CONH2, POR"R"'; R' = Ph (a), MeC6H4 (b), ClC6H4 (c),
t-Bu (e), C4H3O (f); R" = R"' = OMe, OEt, OPr-i R" = OEt, R"' = Ph

, 2

541

2. C 2--4-[b]
2--4-[b] () 1,3- [15],
[8, 10]. , , [8] [49] 1,3-
42c ,
[b] 43 ( 13).
13
O

Ar
X

Ar

R
R'

R
R'

CN

NH2

43

42ac

R = R' = H (a), Me (b); R = H, R' = Ph (c); X = CN, CO2Et, NO2

1,3- 44 3-
, , 45
[50], 2-(3-)-1,3- 46 ( 14).
14
NO2

NO2
CN
X

NO2

CN

X
O

+
HB

XCH2CN
B
44

45

46

X = CN, CO2Et

1,3- 2--1,3,
2,3- 9b
2--4- 47 [15] ( 15). -1,3
, . , , , 542

InterBioScreen

,
[50].
9b , 48,
, 48 [15].
48bd , 49
1,1- 49b [51] 5,5--1,3--2- 50
[52] ( 15).
15
O

O R' R"

OEt
42b

CN

NC

EtO

42b

NH2

CN

NC

R"

O
9b

49a, b

48ad
O

44

O NC CO Et
2
CO2Et
O
47

CN
CN

NH2

CN
CN

50

R = CO2Et, CN; R' = CN, Me; R" = Me (49a), CH(OMe)2 (49b), CN, CO2Et

. , - [49, 50].
, 4-
1,3-, ,
[53].
3--2- 51 ( 16) . ,
51
42a, b 43. ( 42 )
4- 52. , ,
, 2

543

53 54
42 [54].
16
O

CN

NC
CN
CN

R
R

O
R
R

H
N

Cl
CN

Cl

53

O
42a, b

NH2

43a, b

Cl

51
O
R
R

O
NC

H
O
42a, b

N
R
R
54a, b

CN
O

CN

CN

R
R

O
52a, b

R = H (a), Me (b)

4- 55 [55]. 55
56, .
56 1, 42.
, 4- ,
, , , 57 ( 17).
, , [50],
.
544

InterBioScreen

17
R

R
NC
S

H2N

CN

NC

CN

CN

NH2

55

NH2

CN

H2O

CN

NH2
CN

56

CN
NH2

NC

CN

NC

NH2
CN

CN

O
1a, b
.

42b
O

R
CN

CN
N
H

57

NH2

43

R = 4-FC6H4, 2-C4H3O

58 , KF [36], 2--4,4,7--3--5,6,7,8--4[b] ( 18).


18
CN

+
O

CN

CN

KF

NH2

58

1,3- ,
, ,
. , 2- 59 ( 19)
2- (60, 79%) 2-(1) (61, 20%) [56].
-, 59 , 62,
, 2

545


60. 62 63, 61.
19
CN

NC
O

CN

NC
O

CN

30

CN

OH

62

59

H2O

NC
O

63

CN

O
CN

CN
O

NH2

61

60

N
H

2-
, .
[57, 58].
- 4- 64.
5--4- 65 [59] ( 20).
20
OH

OH

CN

HO

CN

NC

OH

CN

NH2

65

CN

O
R
R = Ph, 4-MeC6H4, 2-MeOC6H4, 4-MeOC6H4, 2-ClC6H4,
2,5-MeOC6H3, 3,4-MeOC6H3, 3-Py, 2-C4H3S

546

NH2
64 CN

InterBioScreen

3
- [60] 1,5- 66.
3 ( 21) 1 : 2 67 [61].
2,3- 1,6-, , 1,7- 2,7- , , , - [23].
21
R

OH
NC

R
CN

CN

HO

NC

CN

NH2

OH
66

R
CN
H2N

NH2

NC
R

67

R = 4-ClC6H4, 4-OHC6H4, 3,4-(OCH2O)C6H3

[b] 68 (6190%) ,- 69 22 [62, 63].


22
Ar

R'
R

+
O

Ar

69

CN

R'
R

Ar
X
O

Ar

Ar

R'
R

X
O

NH
Ar

NH2

68

Ar = Ph, 4-MeC6H4, 4-ClC6H4; R = H, t-Bu, CO2Me; R' = H, CO2Me; X = CN, CONH2

.
,
,
[64]. , 5-
, 2

547

3- [65]. 5-(2-) 2--4- [66].


3. 2--4-,
3.1
5- [3,4-b] [67]. , 3--1--5-
[68] 3--5- [10] - 2-[3,4-b].
4--3--1--5- [69] 3-1--5 2-(N--3-)-1,1- [49].
[72] [3,4-b] 70
( 23) 3--5- 71, ( ).
23

Ar

CN

O
H

CN

NC

Ar

CN

CN B

NC

N X
N

Ar

R 71

CN

71

N X
N

CN

NC

N X
N

R
3

Ar

73

CN

OH
N X
N

Ar
R

72

Ar
CN

N
N
X

Ar
CN

N
O

NH

N
X

NH2

74
75
70
Ar = Ph, 2-MeC6H4, 4-MeC6H4, 2-NO2C6H4, 3-NO2C6H4, 4-NO2C6H4,
2-FC6H4, 3-FC6H4, 4-FC6H4, 2-ClC6H4, 4-ClC6H4, 4-BrC6H4, 2-MeOC6H4;
R = Me, Ph, NH2; X = H, Ph .

548

InterBioScreen

3 4-3--5- 72, 71
4-(1--2,2-)3--5- 73. 3 71 ( B),
[3,4-b] 70 c .
2025
4-(1--2,2-)-3--5- 73. , 4--3--5- 72 2- 70 ( C). , , (73
74
75),
C [68] - , 73

(75
70). , , .
, ,
, 73 ( , )
5--3--1--4-(1--2,2-) 74.
4 : 1 6 : 1.
73 70,
[71].
1--3-()-5 [72].
3--5 5--3--5 3,6-[3,4-b],

, [73].
24
S
Ph N
Ph

76a

HN
Ph

Ph

N
Ph

CN
NH2

77

NH

Ph

O
76b

Ph
N
S

CN
CN

N Ph

NC

O
N

H2N

78

NH
S

, 2

549

, . , 76
[3,2-d] 77, 76b [1,2-c] 78 [74] ( 24), .
3.2 -2,
[3,2-c] 79, 25, 4- 80 :
) 3 (Z = CSNH2)
1 . . , 3,4- 2025 4- , 79 .
) 3 (Z = COOEt) .
) 3 (Z = CN) 2025 (82%), [75] [76].
[5].
25
OH

O
Ar

80

CN

X
3

+
O

Ar

NH2

79

Ar = Ph, 4-FC6H4, 4-BrC6H4, 4-HOC6H4, 4-MeOC6H4, 4-EtOC6H4, 2-C4H3O;


X = CN, CO2Et, CSNH2

( 26) 4--6--2- 81
4--6--2- 82, [7778]. ,
81 82 3
83, 84 c .
, 4-() , ,
4-() [77, 78].
5-(X-)-8- (X = NHPh, NHMe,
NMe2, NEt2, N-, N-)
2--4--6-(X-c)-4H-[3,2-h] [80].
550

InterBioScreen

26
OH

N
H
81

Ar
X

HN
O
83

Ar
X

NH2

OH

CN
O
82

Ar
X

O
O
84

NH2

Ar = Ph, 4-i-PrC6H4, 3-OHC6H4, 2-HalC6H4, 4-HalC6H4, 3-NO2C6H4,


4-NO2C6H4, 4-MeC6H4, 4-MeOC6H4, 2-Cl-6-FC6H3, 2,4-ClC6H3, 2-C10H7;
X = CN, CO2Me, CO2Et

4- 4- 85, ,
86, b,
[3,2-c] 87 [3,2-c] 87b.
88 ( 1,3- ) [3] ( 27).
27
CN

NC

OH

CN

NC

NC

9a

OH

CN

80, 85

OH

N
H

OH
OH NC

CN

O NC CN

CN

CN

X
O

CN
X

NH2

86a, b

87a, b

88
X = O (80, 86a, 87a), NH (85, 86b, 87b)

, 2

551

[2, 60] 89 4--2- 90 91 ( 28).


28

OH
X

NH2
N
R

OH

Ar
Y

90

Cl

CN

Ar
N
R

H
N
Et

89

HCO2H

91
Ar = Ph, 4-MeOC6H4, 4-ClC6H4; R = H, Me, Et; X = H, Cl; Y = CN, CO2Et

2- 92, b
4- 93b 2- 94 95 [81, 82] ( 29).
2-, 3.
29
O

O
OH

X
Y
93a, b

Cl

O
OH

X
Y

94a, b

CN

X
Y

Ph

OH

95a, b

O
X
Y

NH2

92a, b
a X = CH, Y = N; b X = N, Y = CH

552

InterBioScreen

1,6-- 1,6- 2-. , 1--2--3-


N- 1--3-[4,3-b] [83].
3.3
96
(~2 : 1) [84, 85] [2,3-d]-2,4(1,3)- 97 ( 30).
30
Ar

O
X

HN
O

N
H

CN

HN
O

99

CN

Ar
N
H

CN

HN
O

98

CN
Ar

N
H

CN

HN

96

OH

X
O
100

Ar

N
H

N
H
101

HN
O

Ar

NH

Ar
X

HN
O

N
H

NH2

97

a Ar = Ph, 4-FC6H4, 4-ClC6H4; X = CO2Et;


b Ar = Ph, 2-HalC6H4, 3-HalC6H4, 4-HalC6H4, 2-NO2C6H4, 3-NO2C6H4, 4-NO2C6H4; X = CN

96 3
(98
99),
(100
97). ,
5- 101
96 .


7--5,5,6--5-[2,3-d]-2,4(1,3)-. ,
(6-2,4--1,2,3,4--5-).
N,N- [67].
, 2

553

4.
, , .
2--4- 102 , , 1a,
1b, 1c
1d, 103 [86]. 4--2- 104 1e, 1f,
1g 1h
105.
104 1eh
102, 104,
( 31).
31

CN

NC

CN

H2N

R
R'
1ad

NC

R'
O
N

O
102

CN

O
104

103
O
O
N
O
( 1eh)

H2N

NC
O

O
105

104 ,
1,3- [87], , , [88],
3--1--5-, [87], 4-,
1,3- [89], 1- [90]
[-3,4'-(2'--4'-)].
2,2--1,3- 1,3- [88]
.
3-(---)-2- 106 4--6--2 ( 32), 3-(,-)-2- 106b
554

InterBioScreen

[82]. , -
107, 106.
32

X = CO2Et
106a
OH

NC

H
O N

HN

CO2Et
O

X
O

N
H

NH2

H
N

N
H
X = CN
106b

106a, b

H
N

CN

CN
.. CN
NH2

NH2

2- [86, 87, 9193].


2,6--(1-2-)--1,3-[4,5-b:4',5'-e] 108 [94] ( 33).
33
O

R
CN

O
S

EtOH

O
S

CN
R

O
S

NC
O

108

, 2

555

OH

CN

NC

HO

NH2

H2 N

O
110

O
109ac

R = CN (a), CONH2 (b), CO2Et (c)

() ,

109, b. 110 109c . ,
- - 110 109, .
2-(1--2-) 111 [95] ( 34). 111 (-6,2') 112. 111
() 113. - .
34
S
H2N

H
N

X = NH2 (a), Me (b)

S S
112a, b

NH
Br
NC

111

CN

O
O

NH
CN

S
Br

HBr

NH

CN
O

CN
CN

113

556

InterBioScreen

() , 1,3- [19, 96, 97]. -5- .


5. 2--4-
2--4- -
, , , .
(
, ), [3].
, 2-3-, [72].
2--4--5--3--4-[3,2-] [75]
[76].
20 ,
, , [9].
R'
R''

R'''

NH2

20
R = Alk, Ph, CO2Alk, CO2CnH(2n2);
R' = Alk, OAlk, CO2Alk, CO2CnH(2n2), Hal, Ar, Py, C4H3S(O), CF3, NO2, CN;
R" = Alk, OAlk, CO2Alk, CO2CnH(2n2), CO2CnH(2n4);
R"' = H, Alk

, ,
, ,
- . , , , ,
, [98].
R'
X

O
R

CN
CN

R"'

N
O S O
R"

NC

NH2
O

114

NH2

115
R = H, MeO

, 2

557

-4(4)- (114, R = H, Hal, NO2,


CN ; R' = Ar, Het; R'' =
, ; R''' = , ; X = O, S NH)

, , , , , [99]. 115 [100].
R
1

R
O

NH2

116
R = Ph, C4H3S, C4H3O; R1 = CN, CO2NH2, CONR2R3; R4SO2;
R2, R3 = H, Alk (C1C4); R4 =Alk (C1C4), Ph;
P

N ;

; N

,
.
116 ,
( , ,
, ) [101].

Rn
R2

R1m

O
117

R4

R3

R = Hal, OH, Alk (C1C4), OAlk (C1C4), NO2, OCF3 ..;


R1 = Hal, OH, OAlk (C1C4), NO2, CF3 ..;
R2 = CN, CO2R; R3, R4 = H, Alk (C1C4), COAlk (C1C4) ..;
n, m = 0, 1, 2

117 , [102].
558

InterBioScreen

118, b
[44]. 2--4--3--4-[1,2-b] 119, b ,
[103].

Ar
CN

X
O

NH2

118a X = CN;
118b X = CO2Et

NH2

119a Ar = 3-Py;
119b Ar = 3-NO2C6H4

2--4- 27, 120 , 1,4-, [38].

R
H O
NC

R*

H2 N

O
27, 120

R = H, 3-NO2, 2-Me, 4-Me, 4-Hal, 4-CN;


O
R* =

O
;

OEt
H

[2,3-d]
[2,3-d],
[104].
, 2

559

R'
O N

Het
X

N
R'

NH2

121a X = CN;
121b X = CO2Et

N
Ph

NH2

122ac
X = CO2Et (a, b), CN (c);
R = 5-F (a, b), 4-CF3 (c);
R' = H (c), COMe (a), CH2N

(b)

[12] 121 ,
.
122c ,
122b, c [92].
, , ,
[13, 77].

1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.

560

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InterBioScreen

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InterBioScreen

87.
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89.
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91.
92.
93.
94.
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Higashiyama K., Otomasu H., Chem. Pharm. Bull. 1980 28 648.


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, 2

563

.. 7
.. 103

.. 149
.. 25
.. 284

.. 36
.. 63, 75

.. 493
.. 206
.. 103
.. 113
.. 437

.. 305
.. 127

a .. 534
.. 75, 149

.. 159

.. 193, 503, 518


564

.. 437
.. 159
.. 206
.. 159
.. 241
.. 241
.. 258
.. 7
.. 149

.. 103
.. 206
.. 284
.. 361
.. 305, 335

.. 206
.. 361
.. 284

.. 113
.. 396
.. 493

.. 103

.. 405
.. 437
InterBioScreen


.. 127
.. 444
.. 206

.. 465

.. 493

.. 193, 503, 518

.. 159
.. 405

.. 518
.. 335
.. 405, 534
.. 305

, 2

565

, 2

066545 12.05.99
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