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Tetrahedron Letters 53 (2012) 962966

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Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet

A facile domino protocol for the stereoselective synthesis


of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3-d]pyrimidines
Beermohamed Vinosha a, Subbu Perumal a,, Subbiah Renuga a, Abdulrahman I. Almansour b
a
b

Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, India
Department of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia

a r t i c l e

i n f o

a b s t r a c t

Article history:
Received 8 November 2011
Revised 9 December 2011
Accepted 12 December 2011
Available online 17 December 2011

A facile protocol for the stereoselective construction of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3-d]pyrimidines from the reactions of 2,20 -sulfonylbis(1,3-diarylprop-2-en-1-ones) with cyclic
1,3-diketones, viz. cyclohexane-1,3-diones, barbituric acid, and 2-thioxodihydropyrimidine-4,6(1H,5H)dione in the presence of DBU in ethanol is described. This transformation presumably occurs via domino
Michael addition-proton exchange-annulation via intramolecular displacement sequence.
2011 Elsevier Ltd. All rights reserved.

Keywords:
Domino reaction
trans-2,3-Dihydrobenzofurans
Stereoselectivity
2,20 -Sulfonylbis(1,3-diarylprop-2-en-1-ones)
Michael addition
Annulation

anticancer,13 antiangiogenic14 and melatoninergic agents,15 highly


selective kappa opioid receptor agonists,16 cyclooxygenase (COX)
and lipoxygenase (LOX), and platelet aggregation inhibitors.17 They
are also useful in the treatment of traumatic and ischemic central
nervous system (CNS) injuries,18 arteriosclerosis, hepatopathy, and
cerebrovascular disease.19 The biological importance of 2,3dihydrobenzofurans stimulated interest in their synthesis via
tandem reaction,20 cyclodehydration,21 cycloadditions,22,23 TBAF-,
Lewis acid-, and transition metal-catalyzed reactions,24 anionic,
electrocyclic and free radical cyclizations, 25 and Sakurai reaction.26

Dihydrobenzofurans belong to an important class of heterocycles, widely embedded in many biologically interesting natural
products,1,2 with important biological activities viz. ()-obtusafuran,3 ()-liliol-B,4 ()-kadsurinone,5 and ()-denudatin6 (Fig. 1).
(+)-Conocarpan (1), rst isolated from the wood of Conocarpus
erectus7 exhibits a diverse array of biological activities, including
insecticidal,8 antifungal,9 and antitrypanosomal properties.10 (+)Lithospermic acid,11 an intensively investigated therapeutic target
for the treatment of AIDS, is a potent and nontoxic anti-HIV agent
that inhibits HIV-1 integrase.12 The 2,3-dihydrobenzofurans act as
Me

Me

HO
O

MeO

HO

OMe

OMe

()-Liliflol-B

()-Obtusafuran

Me

MeO

()-Kadsurinone
O

MeO

Me
OMe

OMe

()-Denudatin

OH

(+)-Conocarpan

OH

OH

CO2H

CO2H O

HO

O
OH

(+)-Lithospermic acid

Figure 1. Representative naturally occurring 2,3-dihydrobenzofurans.

Corresponding author. Tel./fax: +91 452 2459845.


E-mail address: subbu.perum@gmail.com (S. Perumal).
0040-4039/$ - see front matter 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.tetlet.2011.12.047

OH

963

B. Vinosha et al. / Tetrahedron Letters 53 (2012) 962966

Further, the related hybrid heterocycles, furo[2,3-d]pyrimidines


possess important biological activities that include antifungal,27
antifolate,28 antibacterial,29 antitumor,30 antiviral,31 Akt1 Kinase
inhibition,32 and anti-HCMV (human cytomegalovirus).33 This has
led to the development of several multi-step synthesis for
furo[2,3-d]pyrimidine derivatives.34 However, only a few domino
reactions have been reported for the synthesis of furo[2,3-d]pyrimidines,35,36 despite the unique advantages associated with these
reactions in terms of convergence, elegance, maximization of yield,
and minimization of waste, which enhance the greenness of these
synthetic protocols.37
Consequently, the present work describes a stereoselective
construction of trans-2,3-dihydrobenzofurans 6 and 7 and cis5,6-dihydrofuro[2,3-d]pyrimidines 8 and 9 by the reaction of
2,20 -sulfonylbis(1,3-diarylprop-2-en-1-ones) with cyclic 1,3-diketones in the presence of DBU in ethanol in moderate yields with
high stereoselectivity (Scheme 1). This study stems as a part of
our research program embarked on recently to evolve new
methodologies employing tandem/domino reactions for the
construction of novel heterocycles.38
The reaction of 2,20 -sulfonylbis(1,3-diarylprop-2-en-1-ones) 2
(1 mmol) with cyclic 1,3-diketones (1 mmol), viz. cyclohexane1,3-dione, dimedone, barbituric acid, and 2-thioxodihydropyrimidine-4,6(1H,5H)-dione was initially investigated in the presence of
DBU (0.5 mmol) under heating in an oil bath at 80 C for 4 h in
ethanol. After completion of the reaction (TLC) and work-up,
the products, viz. trans-2-aroyl-3-aryl-2,3,6,7-tetrahydrobenzofuran-4(5H)-ones 6 and 7, cis-6-aroyl-5-aryl-5,6-dihydrofuro[2,
3-d]pyrimidine-2,4(1H,3H)-diones 8, and cis-6-aroyl-5-aryl-2-thioxo-2,3,5,6-tetrahydrofuro[2,3-d]pyrimidin-4(1H)-ones 9 (Scheme
1, Table 1) were obtained in 5271% yields39 in a pure form by ash
column chromatography. The reaction of 2,20 -sulfonylbis(1,3diarylprop-2-en-1-ones) 5 with cyclic 1,3-diketones 14 (1 mmol)
in the presence of DBU (0.5 mmol) was also investigated under
microwave irradiation in a focused microwave synthesizer, since
microwave irradiation, in general, accelerates reactions spectacularly, enhances the yield of the product, minimizes the decomposition of the reactants and/or products and shows greater selectivity
than the thermal reactions.40 The optimum conditions for microwave irradiation were found to be 140 C, 50 W power level, 5 bar
pressure, and high absorption level for 25 min (Table 2)39 and the
data in Table 3 disclose that DBU catalyzes the reaction efciently.
The reaction vial after completion of the reaction was cooled and
the product, after work-up, was puried as done for the thermal
reaction.

Table 1
Synthesis of trans-2,3-dihydrobenzofurans 6 and 7 and cis-5,6-dihydrofuro[2,3d]pyrimidines 8 and 9
O

O
or

HN

NH

1, R = H
2, R = CH 3

Ar

O2
S

Ar'

3, X = O
4, X = S

S. No.

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

R
R

or
O
6, R = H
7, R =CH3

Ar

Ar

8, X = O
9, X = S

Ar0

Ar

C6H5
p-ClC6H4
p-ClC6H4
p-CH3C6H4
p-CH3C6H4
C6H5
C6H5
p-ClC6H4
p-ClC6H4
p-ClC6H4
p-ClC6H4
p-CH3C6H4
C6H5
C6H5
p-ClC6H4
p-ClC6H4
p-ClC6H4
p-ClC6H4
p-CH3C6H4
p-CH3C6H4
C6H5
C6H5
p-ClC6H4
p-ClC6H4
p-ClC6H4
p-ClC6H4
p-CH3C6H4

Yielda (%)

Product

C6H5
p-FC6H4
p-CH3C6H4
C6H5
p-ClC6H4
C6H5
p-ClC6H4
C6H5
p-FC6H4
p-ClC6H4
p-CH3C6H4
p-ClC6H4
C6H5
p-ClC6H4
C6H5
p-FC6H4
p-ClC6H4
p-CH3C6H4
C6H5
p-ClC6H4
C6H5
p-ClC6H4
C6H5
p-FC6H4
p-ClC6H4
p-CH3C6H4
p-ClC6H4

6a
6b
6c
6d
6e
7a
7b
7c
7d
7e
7f
7g
8a
8b
8c
8d
8e
8f
8g
8h
9a
9b
9c
9d
9e
9f
9g

Thermalb

MWc

60
63
69
62
71
62
68
65
68
62
60
66
65
52
56
52
66
67
61
56
52
58
53
54
66
62
52

72
65
72
70
74
69
76
70
75
68
67
70
67
60
62
58
73
75
66
62
58
62
64
61
68
68
63

Table 2
Temperature-optimization for the DBU-catalyzed formation of 7d under microwave
irradiation
S. No.

Temp. (C)

Irradiation time (min)

Yielda of 7d (%)

1
2
3

100
120
140

45
35
25

42
48
75

Isolated yield after purication by column chromatography.

Ar

Table 3
Base-screen for the synthesis of trans-2,3-dihydrobenzofurans 7d
S. No.

1
2
3
4
5

Ar'
a

N
H

Isolated yield after purication by column chromatography.


Heated under reux in ethanol for 4 h.
c
Irradiated in ethanol at 140 C at 200 W power level and 5 bar pressure for
25 min.

O
N
H

Ar'

HN

Ar

EtOH, MW, 25 min

1
1
1
1
1
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4

Ar'

1,3-Diketone

Ar'

HN

6, R = H
7, R =CH3

DBU

Ar'

Base

K2CO3
Et3N
t-BuOK
NaOEt
DBU

Reaction time

Yield (%)
a

MW (min)

Thermal (h)

MW

Thermala

25
25
25
25
25

7
6
8
4
5

36
38
39
68
75

32
35
35
63
68

Isolated yield after purication by column chromatography.

Ar

8, X = O
9, X = S

Scheme 1. Synthesis of trans-2,3-dihydrobenzofurans (6 and 7) and cis-5,6dihydrofuro[2,3-d]pyrimidines (8 and 9).

The special inuence of microwaves, besides heating, was not


assessed, as the reactions were conducted under thermal and
microwave irradiations at different temperatures. It is, however,
to be noted that the microwave reaction affords a slightly higher

964

B. Vinosha et al. / Tetrahedron Letters 53 (2012) 962966

Cl

2.16, d; 2.24, d
193.5
(J = 16.2 Hz)
51.0
Hb O
Ha
H
H3 C
5.82, d, J = 4.2 Hz
H
34.3
1.15, s, 6H
O
H3C
28.3, 28.9
91.4
O
Ha
Hb

O
H
H3 C 5

4H
3a

H3C 6

7a
H
7

[6a (66%), 6d (66%)41a, 7a (63%), 7b (75%),42 and 7c (45%)].20a The


present method is expedient and employs readily accessible reactants, besides the fact that the syntheses of compounds of series 8
and 9 are now being reported for the rst time, which also brings
out the generality of the method.
The structure of trans-2,3-dihydrobenzofurans is in accord with
elemental analyses and 1H, 13C, and 2D NMR spectroscopic data as
illustrated for a representative example 7g. In the 1H NMR spectrum of 7g, the two methyl groups of the cyclohexenone part
appearing as a singlet at 1.15 ppm showed HMBCs with C-6 at
34.3 and C-5 at 51.0 ppm (Fig. 2). The H-2 and H-3, related by a
H,H-COSY correlation, appeared as doublets, respectively, at 5.82
and 4.37 ppm (J = 4.2 Hz) revealing their trans-relationship. These
hydrogens showed HMBCs (Fig. 2) with C-7a at 176.5 ppm and C3a at 114.8 ppm. The 5-CH2 hydrogens appearing as doublets at
2.16 and 2.24 ppm (J = 16.2 Hz) showed a C,H-COSY correlation
with a carbon signal at 51.0 ppm enabling its assignment to C-5
and also HMBCs with C-6 at 34.3, C-7 at 37.6 and C-4 at
193.5 ppm. The doublets at 2.51 and 2.62 ppm (J = 17.7 Hz) of 7CH2 hydrogens show a C,H-COSY correlation with carbon at
37.6 ppm and HMBCs with C-5 at 51.0, C-7a at 176.5 ppm, and C3a at 114.8 ppm. The structure determined from an X-ray crystallographic study of a single crystal of 7g43 conrms the structure
deduced from NMR spectroscopic studies (Fig. 3).
A plausible mechanism for the formation of trans-2,3-dihydrobenzofurans (Scheme 2) envisages an initial Michael addition
of the enolate of cyclic 1,3-diketones 1 and 2 to 2,20 -sulfonylbis(1,3-diaryl-prop-2-en-1-ones) 5 to give 10, which undergoes
proton exchange to afford 11. Subsequently, enolate 11 undergoes
annulation through the displacement of the sulfonyl moiety44 to
furnish dihydrobenzofurans, 6 and 7. The other diastereomer of 11,
viz. 110 is bound to suffer from more steric as well as eclipsing-like
interactions between the aroyl and aryl groups in the transition state
and hence raise the energy of activation for the annulation leading to
cis-2,3-dihydrobenzofurans relative to trans isomer-6/7.
The stereochemistry of the dihydrofuro[2,3-d]pyrimidines 8 and
9 could not be determined by X-ray crystallographic studies, as crystals of two compounds studied, viz. cis-6-(4-chlorobenzoyl)-5-(4chlorophenyl)-5,6-dihydrofuro-[2,3-d]pyrimidine-2,4(1H,3H)-dione
8e and cis-6-(4-chlorobenzoyl)-5-phenyl-2-thioxo-2,3,5,6-tetrahy-

4.37, d, J = 4.2 Hz
48.4 Cl

3 H
O

O 2
1

2.51, d; 2.62, d
(J = 17.7 Hz)
37.6

CH3

CH3

Figure 2. Selected HMBCs and chemical shifts in 7g.

Figure 3. ORTEP diagram of 7g.

yield of the product, 69 (5875%) in a shorter time than the thermal method (5271%) under the conditions employed. It is pertinent to note that ve compounds belonging to series 6 and 7,
viz. 6a, 6d, 7a, 7b, and 7c obtained in the present work have been
previously reported and their yields in the present method [6a
(72%), 6d (70%), 7a (69%), 7b (76%), and 7c (70%)] are either comparable to or higher than that reported in the literature methods

R1
SO2

B:
O

Ar

1, R = H
2, R = CH3

Ar
O O

R
5

R
O

SO2R

ArOC
O-

COAr

O
Ar

annulation
R =

SO2R1

11'

11

H
H

10

OAr

O Ar

proton
exchange

O 2 S R1

Ar'

O Ar'

Michael
addition

-R1 -SO2

Ar'
O

O
Ar'

Ar'
O

O
R

R
R

O
6, R = H
7, R =CH3

Ar

O
6', R = H
7', R =CH3

Scheme 2. Probable mechanism for the formation of trans-2,3-dihydrofurans 6 and 7.

Ar

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B. Vinosha et al. / Tetrahedron Letters 53 (2012) 962966


Ar'
O

H
N

H
SO2 R1
H

X
N

O- H O

H
N

B:
X

C Ar

Ar'
O

SO2R1

ArOC
H

O-

HN
O

3, X = O
4, X = S
O

HN

O
N
H

Ar'

Ar'

HN
X

Ar

X
O

Ar'

X
Ar

N
H

Ar

8, X = O
9, X = S

8', X = O
9', X = S

Scheme 3. Plausible mechanism for the formation of cis-5,6-dihydrofuro[2,3-d]pyrimidines 8 and 9.

dro-furo[2,3-d]pyrimidin-4(1H)-one 9c exhibited polymorphism,


rendering the structural assignment difcult. Consequently, the
stereochemistry of the compounds 8 and 9 was deduced from their
NMR spectroscopic data which reveal that the aryl and aroyl groups
are in cis-relationship as evident from high J value (12 Hz)39 for the
dihydrofuran ring hydrogens.
The origin of the divergent stereochemistry of the apparently
related compounds, 6/7 and 8/9 suggests that the mechanisms of
formation of these compounds probably differ. Accordingly, a
probable mechanism for the formation of furopyrimidines, 8 and
9 depicted in Scheme 3 has been visualized, wherein the annulation presumably occurs via the displacement of the sulphonyl
moiety by the oxygen of the amide anion. Though the two diastereomeric anions A and B are readily interconvertible in the presence of a base and each can adopt different conformations of
varying stabilities, the conformations that could facilitate the
annulation need to comply with the stereoelectronic requirement,
viz. the nucleophilic oxygen anion and the sulfonyl group should
be on opposite faces of the carbon under attack. It is pertinent to
note that the conformer A of one diastereomer (Scheme 3) would
be highly unstable because of steric and/or electronic interactions,
rendering it inaccessible (as it can adopt other more stable conformations) which would impede the formation of the trans-80 /90 . This
explains the exclusive formation of cis-8/9 from the conformation
B of other diastereomer.
In conclusion, a facile stereoselective protocol for the synthesis
of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3d]pyrimidines in moderate yields from the domino reactions of
2,20 -sulfonylbis(1,3-diarylprop-2-en-1-ones) and cyclic 1,3-diketones in the presence of DBU in ethanol under microwave irradiation as well as conventional thermal method is described. This
study has also brought to light interesting mechanistic as well as
stereochemical aspects of the annulation step of the domino
transformation.
Acknowledgments
B.V., S.P. and A.I.M. acknowledge the Deanship of Scientic
Research at the King Saud University for the Research Grant
RGP-VPP-026.
Supplementary data
Supplementary data associated with this article can be found, in
the online version, at doi:10.1016/j.tetlet.2011.12.047.

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General procedure for the synthesis of 6-9: Conventional method: A mixture of
2,20 -sulfonylbis(1,3-diarylprop-2-en-1-ones) 5 (1 mmol), cyclic 1,3-diketones
14 (1 mmol) and DBU (0.5 mmol) in ethanol (20 mL) was heated under reux
at 80 C for 4 h. After completion of the reaction (TLC), the reaction mixture
was concentrated under vacuum and the residue subjected to ash column
chromatography using petroleum etherethyl acetate mixture [4:1 (v/v)] as
eluent to obtain pure 69. Microwave irradiation: A mixture of 2,20 sulfonylbis(1,3-diarylprop-2-en-1-ones) 5 (1 mmol), cyclic 1,3-diketones 14
(1 mmol) and DBU (0.5 mmol) in ethanol (5 ml) was taken in a 10 ml quartz
vial which was sealed and subjected to microwave irradiation in a Biotage
focused microwave oven at 140 C, 50 W, 5 bar pressure and maximum
absorption level. After about 4 min, the temperature reached 140 C, and
remained constant thereafter. After 25 min the vial was gas jet cooled to room
temperature (5 min), and the product after work-up was puried as done for
the thermal reaction. Spectroscopic data for a representative compound in
each series, 69 are given below.
trans-3-(4-Chlorophenyl)-2-(4-methylbenzoyl)-2,3,6,7-tetrahydrobenzofuran4(5H)-one (6e): Isolated as white solid. Yield: 74%; mp = 106109 C; IR (KBr):
1230, 1405 cm1 (CO), 1637, 1691 cm1 (C@O); 1H NMR (300 MHz, CDCl3) dH:
1.962.00 (m, 2H, H-6), 2.19 (t, 2H, J = 7.2 Hz, H-7), 2.29 (s, 3H, CH3), 2.57 (t,
2H, J = 5.7 Hz, H-5), 4.29 (d, 1H, J = 4.8 Hz, H-3), 5.69 (d, 1H, J = 4.8 Hz, H-2),
7.06 (d, 2H, J = 8.1 Hz, Ar-H), 7.13 (d, 2H, J = 8.1 Hz, Ar-H), 7.19 (d, 2H,
J = 8.4 Hz, Ar-H), 7.59 (d, 2H, J = 8.4 Hz, Ar-H). 13C NMR (75 MHz, CDCl3) dC:
21.4, 21.5, 23.6, 36.4, 48.0, 90.9, 115.8, 128.5, 128.7, 128.8, 129.4, 130.4, 132.9,
139.5, 145.1, 177.3, 191.9, 193.9. Anal. Calcd for C22H19ClO3: C, 72.03; H, 5.22%.
Found: C, 72.16; H, 5.31%.
trans-3-(4-Chlorophenyl)-6,6-dimethyl-2-(4-methylbenzoyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one (7g): Isolated as white solid. Yield: 70%; mp = 173
176 C; IR (KBr): 1222, 1400 cm1 (CO), 1639, 1697 cm1 (C@O); 1H NMR
(300 MHz, CDCl3) dH: 1.15 (s, 6H, 2CH3), 2.16 (d, 1H, J = 16.2 Hz, H-5), 2.24 (d,
1H, J = 16.2 Hz, H-5), 2.42 (s, 3H, CH3), 2.51 (d, 1H, J = 17.7 Hz, H-7), 2.62 (d, 1H,
J = 17.7 Hz, H-7), 4.37 (d, 1H, J = 4.2 Hz, H-3), 5.82 (d, 1H, J = 4.2 Hz, H-2), 7.17
(d, 2H, J = 8.1 Hz, Ar-H), 7.21 (d, 2H, J = 7.8 Hz, Ar-H), 7.32 (d, 2H, J = 7.8 Hz, ArH), 7.70 (d, 2H, J = 8.1 Hz, Ar-H). 13C NMR (75 MHz, CDCl3) dC: 21.8, 28.3, 29.0,
34.3, 37.6, 48.4, 51.0, 91.4, 114.8, 128.7, 129.0, 129.2, 129.6, 130.6, 133.3,
139.8, 145.4, 176.5, 192.1, 193.5. Anal. Calcd for C24H23ClO3: C, 73.00; H, 5.87%.
Found: C, 72.92; H, 5.80%.
cis-6-(4-Chlorobenzoyl)-5-(4-chlorophenyl)-5,6-dihydrofuro[2,3-d]pyrimidine2,4(1H,3H)-dione (8e): Isolated as white solid. Yield: 73%; mp = 224226 C; IR
(KBr): 1282, 1367 cm1 (CO), 1716, 1768 cm1 (C@O) 3484, 3558 cm1 (NH);
1
H NMR (300 MHz, DMSO-d6) dH: 4.72 (d, 1H, J = 12.0 Hz, H-5), 6.91 (d, 1H,
J = 12.0 Hz, H-6), 7.06 (d, 2H, J = 7.5 Hz, Ar-H), 7.35(d, 2H, J = 7.5 Hz, Ar-H), 7.66
(d, 2H, J = 8.7 Hz, Ar-H), 8.12 (d, 2H, J = 8.7 Hz, Ar-H). 13C NMR (75 MHz, DMSOd6) dC: 48.8, 58.0, 64.8, 128.7 (2C), 128.8, 130.5, 131.9, 133.1, 134.4, 139.8,
147.4, 169.7, 170.4, 185.7. Anal. Calcd for C19H12Cl2N2O4: C, 56.60; H, 3.00; N,
6.95%. Found: C, 56.52; H, 3.09; N, 6.83%.
cis-5-(4-Chlorophenyl)-6-(4-methylbenzoyl)-2-thioxo-2,3,5,6-tetrahydrofuro[2,3-d]pyrimidin-4(1H)-one (9g): Isolated as white solid. Yield: 63%; mp
>300 C; IR (KBr): 1189 cm1 (C@S), 1284, 1311 cm1 (CO), 1664,
1643 cm1 (C@O), 3222, 3328 cm1 (NH); 1H NMR (300 MHz, DMSO-d6) dH:
2.38 (s, 3H, CH3), 4.73 (d, 1H, J = 12.0 Hz, H-5), 6.86 (d, 1H, J = 12.0 Hz, H-6),
7.03 (br s, 2H, Ar-H), 7.32 (br s, 2H, Ar-H), 7.39 (d, 2H, J = 7.8 Hz, Ar-H), 7.98 (d,
2H, J = 7.8 Hz, Ar-H). 13C NMR (75 MHz, DMSO-d6) dC: 20.8, 49.0, 58.4, 64.3,
128.8, 128.9 (2C), 129.3, 132.0, 133.1, 133.5, 145.6, 167.9, 168.2, 176.3, 185.8.
Anal. Calcd for C20H15ClN2O3S: C, 60.22; H, 3.79; N, 7.02%. Found: C, 60.34; H,
3.86; N, 7.14%.
Caddick, S.; Fitzmaurice, R. Tetrahedron 2009, 65, 33253355.
(a) Ye, Y.; Wang, L.; Fan, R. J. Org. Chem. 2010, 75, 17601763; (b) Maiti, S.;
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Ceylan, M.; Fndk, E. Synth. Commun. 2008, 38, 10701077.
Crystallographic data (excluding structure factors) for compound 7g in this
letter have been deposited with the Cambridge Crystallographic Data Centre as
supplementary publication numbers CCDC 789575. Copies of the data can be
obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge
CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
Vinosha, B. M.; Renuga, S.; Gnanadeebam, M.; Perumal, S.; Lycka, A. Synth.
Commun. 2009, 39, 27762788.