02 Hadithi

SYNTHESIS, CHARACTERIZATION AND KINETIC
STUDIES OF ETHYLENE-[1,3]OXAZINAN -4,6DIONE, CARBONYL-[1,3]OXAZINAN-4,6-DIONE AND

THIOCARBONYL-[1,3]OXAZINAN-4,6-DIONE
FROM REACTION OF SCHIFF-BASES OF
ETHYLENE DIAMINE, UREA AND THIOUREA WITH
MALONIC ANHYDRIDE
Mohamme d A. Al-Hadithi
Chemistry Department, College of Science, University of Al-Anbar, Iraq
ABSTRACT
N-benzylidene2-({2-[(2-hydroxy-benzylidene)-amino]-ethylimino}-methyl)phenol,1,3-Bis-(2-hydroxy-benzylidene)-urea and1,3-Bis-(2-hydroxy-benzylidene)Thiourea (Schiff bases) were prepared by condensation of Ethylene

diamine,urea and thiourea with Salicylaldehyde and 4-dimethyl amine
benzaldhyde. These Schiff bases were reacted with Malonic anhydride by
refluxing it in absolute ethanol at 78C for 1,3 and 2 hrs. respectively to give a
six-membered heterocyclic ring system; 2-(2-hydroxy-phenyl)-3-{2-[2-(2-hydroxyphenyl)-4,6-dioxo-[1,3]oxazinan-3-yl]-ethyl}-[1,3]oxazinan-4,6-dione,2-(2-hydroxyphenyl)-3-[2-hydroxy-phenyl)-4,6-dioxo-[1,3]oxazinan-3-carbonyl]-[1,3]oxazinan4,6-dione and 2-(2-hydroxy-phenyl)-3-[2-hydroxy-phenyl)-4,6-dioxo-[1,3]oxazinan3-thiocarbonyl]-[1,3]oxazinan-4,6-dione.
The costants of reaction velocity for the compounds (Schiff-bases) with
(malonic anhydride) were studied and showed that the reaction was a first-order
one. Some of the thermodynamic characteristics were evaluated and showed
differences among the prepared compounds. The final products were identified by
their melting points, elemental analysis, IR, 1H NMR and UV-Visible spectra.
Keywords: Schiff bases; oxazinan; synthesis; properties; kinetic studies.
-4 , ) (
78 .
6,4 -(-- 2)- 2 ]-2 }- 3-(- -2)-2 :( 2)
-2)-2 ]-3-(--2)-2 , 6,4 --[3,1]- {- [- 3- [ 3,1] -
October 2006
University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3
25
Synthesis, Characterization and Kinetic Studies of Ethylene-[1,3]Oxazinan -4,6-Dione, Carbonyl-[1,3]Oxazinan4,6-Dione and Thiocarbonyl-[1,3]Oxazinan-4,6-Dione from Reaction of (Schiff-Bases) of Ethylene Diamine,
Urea and Thiourea with Malonic Anhydride
--2)- - 64- - [-3- [ 31]1- -64-(-

.- 64- - [ - 3- [ 31]1- -64-(-- 2)- 2 ]- 3-(
. UV. 1HNMR,IR,
) (
. ,
1. INTRODUCTION
The sixmembered heterocyclic ring system: 1,3-oxazine has
already been reported and thoroughly reviewed in the literature [1-4].
Maleic, arylmaleic and substituted maleic anhydrides react with
trimethylsilyl azide to give 4- and 5-substituted "oxauraciles": dihydro1,3-oxazine-2,6-diones [5,6].
Both 2-methoxypyrroline and 2-methoxypiperdinine react with
diketene under netural conditions at 0C to give the corresponding,2methoxydihydro 1,3-oxazine-4-ones [7,8].
Diketene reacts with N,N-diphenyl guanidine to give the tranquilizer
ketazolam and N- substituted tetrahydro-1,3-oxazine-4-one respectively
[9-10]. The reaction of diketene with isocyanic acid, cyanamides and
flourosulphinyl isocyanate afforded the corresponding 1,3-oxazine-2,4diones [11,13].
Ethyl benzimidate,and ethyl butyrimidate react with diketene to give
2-ethoxy-1,3-oxazine- 4-ones [14]. Imines and N-acyl imines react with
diketen to give tetrahydro-1,3-oxazine-4-ones [15,16].
N-acyl imines undergo [4+2] cycloaddition with both-C=C- and
heterodienes. For instance, isolable bis(trifluoromethyl)acyl imine,reacts
with 2,2-dimethylethylene to give 1,3-oxazine.
N-acyl Ammonium ions have been the most commonly used dienes
to effect [4+2] cycloaddition as 4 components with substituted 1,3butadienes. It is found that N-acylimimes or immonium ions that are
capable of tautomerization undergo intramolecular Diels-alder reaction
to give dihydro-1,3-oxazines [17].
26
October 2006
Mohammed A. Al-Hadithi (25- 45)
The reaction of N-benzylidene 1,5-dimethyl-2-phenylpyrazolonamines

(Schiff bases with cyclopentane -1,1-dicarboxylic anhydride to give 2-aryl3-3(1,5-dimethyl-2-phenylpyrazolo)-1-(5) spirocyclopentyltetra hydro-1,3oxazine-4,6-diones [18].
Synthesis and characterization of 8-(4-dimethyl amino-phenyl)-9-(6R- benzothiazol-2-yl)-7-oxa-9-aza-spiro[4.5]decane-6,10-dione [19].
2. EXPERIMENTAL METHODS
Melting points were recorded with Gallenkamp Melting point
Apparataus and were uncorrected. Elemental analysis were carried out
with perkin-Elmer,2400;CHN Elemental Analyzer. FT-IR spectra were
recorded on FT-IR spectrophotometer -8400s Shimadza (KBr) and UVVisible spectra were recorded (in ethanol) on Schimadza Reco- 160
Spectrophotometer. Their H-NMR spectra were recorded with
BRUKERAC200MHZFT NMR spectrophotometer.
Preparation
of
N-(4-Dimethylamino-benzylidene)-N`-(4Dimethylamino-benzylidene)-ethan-1,2 diamine: A mixture of 0.01
mole (0.6 g) of ethylene diamine and 0.01 mole (1.66 g) of 4dimethylamino benzaldehyde in 10 ml of absolute ethanol, was refluxed in
a water bath for 30 min, then left to cool in icewater bath whereby yellow
crystalline solid was precipitated. The solid was filtered, washed with
2%HCl, then with water and recrystallized twice from ethanol.
Preparation of 1,3-Bis-(2-hydroxy-benzylidene)-urea: A mixture
of 0.01 mole (0.6 g) of urea and 0.01 mole (1.22 g) of ohydroxybenzaldehyde in 10 ml of absolute ethanol, was refluxed in a
water bath for 45 min, then left to cool in icewater bath whereby yellow
Preparation of 1,3-bis-(2-hydroxy-benzylidene)-thiourea: A
mixture of 0.01 mole (0.76 g) of thiourea and 0.01 mole (1.22 g) of ohydroxybenzaldehyde in 10 ml of absolute ethanol, was refluxed in a
October 2006
27
water bath for 1hr, then left to cool in icewater bath whereby yellow
Preparation of 3-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-2(2-hydroxy-phenyl)-[1,3]oxazinan-4,6-dione: In a 100 ml round
bottom flask equiped with a double surface condenser fitted with
calcium chloride guard tube, was placed a mixture of 0.01mol (2.68 g)
of
(4-2-({2-[(2-hydroxy-benzylidene)-amino]-ethylimino}-methyl)phenol and 0.01 mol (0.86 g) of malonic anhydride in 20ml of absolute
ethanol. The reaction mixture was refluxed in water bath at 78C for
2hr., the solvent was then removed and the resulting solid was
recrystallized from anhydrous THF.
Preparation of 2-(2-hydroxy-phenyl)-3-{2-[2-(2-hydroxy-phenyl)4,6-dioxo-[1,3]oxazinan-3-yl]-ethyl}-[1,3]oxazinan-4,6-dione: In a 100
ml round bottom flask equiped with a double surface condenser fitted
with calcium chloride guard tube, was placed a mixture of 0.01mol (2.68
g) of 3-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-2-(2-hydroxy-phenyl)[1,3]oxazinan-4,6-dione and 0.01 mol (0.86 g) of malonic anhydride in
20ml of absolute ethanol. The reaction mixture was refluxed in water bath
at 78C for 2hr., the solvent was then removed and the resulting solid was
recrystallized from anhydrous THF.
Preparation of 2-(4-dimethylamino-phenyl)-4,6-dioxo-[1,3] oxazinan
-3-carboxylicacid-4-dimethylaminobenzylideneamide: In a 100 ml
round bottom flask equiped with a double surface condenser fitted with
calcium chloride guard tube, was placed a mixture of 0.01 mol (3.22 g) of
1,3-bis-(4-dimethylamino-benzylidene)-urea and 0.01 mol (0.86 g) of
malonic anhydride in 20ml of absolute ethanol. The reaction mixture was
refluxed in water bath at 78C for 3hr., the solvent was then removed and
the resulting solid was recrystallized from anhydrous 1,4-dioxan.
Preparation of 2-(4-dimethylamino-phenyl)-3-[2-(4-dimethylamino phenyl)-4,6-dioxo-[1,3]oxazinan-3-carbonyl]-[1,3]oxazinan-4,6-dione:
In a 100 ml round bottom flask equiped with a double surface condenser
28
October 2006
fitted with calcium chloride guard tube, was placed a mixture of 0.01mol
(4.085 g) of 2-(4-dimethylamino-phenyl)-4,6-dioxo-[1,3]oxazinan-3carboxylicacid-4-dimethylaminobenzylideneamide and 0.01 mol (0.86 g)
of malonic anhydride in 20ml of absolute ethanol. The reaction mixture
was refluxed in water bath at 78C for 3hr., the solvent was then removed
and the resulting solid was recrystallized from anhydrous 1,4-dioxan.
Preparation of 2-(4-Dimethylamino-phenyl)-4,6-dioxo-[1,3]oxazinan
-3-carbothioicacid-4-dimethylaminobenzylideneamide: In a 100 ml
round bottom flask equiped with a double surface condenser fitted with
calcium chloride guard tube, was placed a mixture of 0.01 mol (3.38 g)
of 1,3-bis-(4-dimethylamino-benzylidene)-thiourea and 0.01 mol (0.86
g) of malonic anhydride in 20ml of absolute ethanol.
The reaction mixture was refluxed in water bath at 78C for 3hr., the
solvent was then removed and the resulting solid was recrystallized from
anhydrous THF.
Preparation of 2-(4-dimethylamino-phenyl)-3-[2-(4-dimethylamino phenyl)-4,6-dioxo-[1,3]oxazinan-3-thiocarbonyl]-[1,3]oxazepane-4,7dione: In a 100 ml round bottom flask equiped with a double surface
condenser fitted with calcium chloride guard tube, was placed a mixture
of 0.01mol (4.24g) of 2-(4-dimethylamino-phenyl)-4,6-dioxo[1,3]oxazinan-3-carbothioicacid-4-dimethylaminobenzylideneamide
and 0.01 mol (1.0 g) of succinic anhydride in 20ml of absolute ethanol.
The reaction mixture was refluxed in water bath at 78C for 3hr., the
solvent was then removed and the resulting solid was recrystallized from
anhydrous 1,4-dioxan.
3. DISCUSSION
It is known that Schiff bases react smoothly with acid chlorides and
anhydrides to give the corresponding addition products [20-22].
The reaction is followed by the appearance of (N=CH) absorption
band at (1600-1610) cm-1 the disappearance of both (C=O) absorption
October 2006
29
band at (1670-1685) cm-1 and (-NH2) absorption bands at (3400,3650)

cm-1 in their IR spectra.
In this paper,the reaction of the malonic anhydride with(4-2-({2-[(2hydroxy-benzylidene)-amino]-ethylimino}-methyl)-phenol gives the
dipolar intermediate [11A] which collapses to the 6-membered
hetrocyclic ring system [11B] is presented.
(Z)
Ethanol
O C
O
HO
(Z)
O
C
O
OH
water bath/ reflx
OH
O
HO
N
O
O
C
O C
[11A]
O
N
HO
C O
C
OH
N
O
C O
C
[11B]
This is indicated by the appearance of the characteristic C=O

(lacton-lactam) absorption band at 1700cm-1 in the IR spectra of the
addition products [11B].
It is impressive to note that the two absorption band at (18001950)cm-1 in the IR spactra of pure malonic anhydride and 2-Oxaspiro[3.4] octane-1,3-dione (anhydride) have disappeared when the
anhydride became part of the 6-membered ring system of the 2-(2hydroxy-phenyl)-3-{2-[2-(2-hydroxy-phenyl)-4,6-dioxo-[1,3]oxazinan3-yl]-ethyl}-[1,3]oxazinan-4,6-dione and 6-(4-dimethylamino-phenyl)7-{2-[2-(4-dimethylamino-phenyl)-4,6-dioxo-[1,3]oxazinan-3-yl]ethyl}-5-oxa-7-aza-spiro[2.5]octane-4,8-dione.
30
October 2006
The new absorption bands of the (C=O) group in the IR spectra of

the addition products [11B] appear at (1670-1700)cm-1, this is attributed
to the fact that the structures of the addition products are combination of
the lacton-lactam structure.
The UV spectra of 2-(2-hydroxy-phenyl)-3-{2-[2-(2-hydroxy-phenyl)4,6-dioxo-[1,3]oxazinan-3-yl]-ethyl}-[1,3]oxazinan-4,6-dione and 6-(4Dimethylamino-phenyl)-7-{2-[2-(4-Dimethylamino-phenyl)-4,6dioxo[1,3]oxazinan-3-yl]-ethyl}-5-oxa-7-aza-spiro[2.5]octane-4,8-dione
show
absorption maxima at (240-310)nm, and at (310-445)nm due to charge
transfer of the aryl group and the cyclic 6-membered structure [11B].
2-(2-hydroxy-phenyl)-3-{2-[2-(2-hydroxy-phenyl)-4,6-dioxo-[1,3]
oxazinan-3-yl]-ethyl}-[1,3]oxazinan-4,6-dione and 6-(4-Dimethylaminophenyl)-7-{2-[2-(4-Dimethylamino-phenyl)-4,6dioxo-[1,3]oxazinan-3-yl]ethyl}-5-oxa-7-aza-spiro[2.5]octane-4,8-dione are identified by their melting
points, elemental analysis(Table 1),IR spectra (Table 2) and UV spectra
(Table 3). It is noticeable that the values of C-H str. (benzylic) absorption
bands are rather high.This is in fact explained by the shift towards longer
wavelength, that takes place when the benzylic carbon is linked to three
electron-withdrawing groups,phenyl, O and N in the title compounds.
The reaction of 2-Oxa-spiro[3.4] octane-1,3-dione with various
Schiff bases is a sort of cycloaddition reaction.Cycloaddition is a ring
formation that results from the addition of bonds to either or with
formation of new bonds.This class of reactions and its reverse
encompasses a large number of individual types. Huisgen [23]. has
formulated a useful classification of diverse cycloaddition in terms of the
number of the new bond, The ring size of the product, and the number
of atoms in the components taking part in the
cycloaddition. This cycloaddition reaction is classified as a 2 + 5-7,
and it is the first cycloaddition of this type, although in principle, one
would predict that the butadienyl cation might add to an oleftin through
a (4n+2) transition state to yield the cyclohexenyl cation [24].
October 2006
31
Table 1. Melting points, yield, molecular formula [M.F], elemental analysis and UV-Visible
absorption maxima (nm) of ethylene [1,3] oxazinan-4,6-dione (1-8).
No.
1
2
3
4
5
6
7
8
M.P/C
192194
204206
210212
160162
166168
167169
126128
174176
Yield%
M.F.
Calculated
Found
UV-Visible absorption
Maxima (nm)
C%
H%
N%
C%
H%
N%
66
C12 H14 N2 O4
57.59
5.64
11.19
57.66
5.70
11.31
482,454,3,51,301,224,202
73
C19 H18 N2 O5
64.40
5.12
7.91
64.35
15.20
7.74
485,459,375,310,225,205
80
C22 H20 N2 O8
60.00
4.58
6.36
59.89
4.62
6.23
346, 315,289,2,75,252,207
77
C14 H19 N3 O3
60.63
6.91
15.15
60.71
7.02
15.11
478,345,312,286,250,224
69
C23 H28 N4 O3
67.63
6.91
13.72
67.60
7.00
13.59
474,376,300,299,264,223,
82
C26 H30 N4 O6
63.15
6.11
11.33
63.10
5.99
11.23
471,340,311,291,257,220
69
C23 H22 N2 O8
60.79
4.88
6.16
60.81
5.00
6.10
445,430,398,368,264,232
75
C27 H32 N4 O6
63.77
6.34
11.02
63.59
6.33
11.00
456,326,288,261,249,227
Table 2. The major IR absorptions (cm-1) of ethylene [1,3]oxazinan-4,6-dione (1-8).

No.
OHstr.
phenol
NH2
C-H str.
benzylic
C=Ostr.
Lacton
C=Ostr.
Lactam
C=Nstr.
Imine
C=Cstr.
Aromatic
C-O str.
Lacton
CH bend.
Aromatic
3470
3450,3420
3230
1690
1645
1610
1560
1330
760
3480
3220
1690
1650
1600
1570
1320
780
3440,3410
3220
1695
1650
1610
1570
1310
780
3230
1700
1650
1610
1560
1300
770
3475
3225
1695
1640
1605
1590
1320
780
3225
1680
1640
1600
1580
1285
760
3490
3200
1690
1645
1610
1580
1300
760
3200
1685
1640
1600
1570
1310
770
Table 3. The major 1H NMR absorptions (ppm) of ethylene [1,3] oxazinan-4,6-dione (1-8).
No.
1
2
3
4
5
6
7
8
32
-NH2
2.1
2.1
-
CH2
C N
H2
2.8, 3.5
3.5, 3.7
2.75, 3.4
2.75, 3.4
3.4
3.41, 3.72
3.41, 3.72
3.43
C
H2
3.0
3.1
3.0
3.05
3.1
3.1
3.15
3.15
OH
O
C
H2
7.2
7.2
7.2
7.1
7.2
7.22
7.2
7.2
4.8
4.9
4.9
4.85
-
H 3C
2.75
2.75
2.75
_
2.75
CH3
H2
C C
H2 C O
_
_
_
_
_
_
2.5
2.51
Benzene
ring
6.5-7.0
6.5-7.1
6.5-7.0
6.5-7.5
6.5-7.5
6.5-7.0
6.5-7.1
6.5-7.1
October 2006
absorption maxima (nm) of carbonyl [1,3]oxazinan-4,6-dione (9-16).
Calculated
No.
M.P/C
Yield
%
M.F.
214216
208210
190192
125127
136138
200202
128130
146148
57
10
11
12
13
14
15
16
Found
Maxima (nm)
C%
H%
N%
C%
H%
N%
C11 H10 N2 O5
52.80
4.03
11.20
52.77
4.00
11.15
389,336,322,277,248,221
66
C18 H14 N2 O6
61.02
3.98
7.91
60.98
4.03
7.88
393,345,303,235,223,213
67
C13 H15 N3 O4
56.31
5.45
15.15
56.42
5.56
15.12
386,358,317,282,249,225
68
C22 H24 N4 O4
64.69
5.92
13.72
64.76
6.04
13.65
412,396,375,266,246,220
67
C21 H16 N2 O9
57.28
3.66
6.36
57.34
3.73
6.33
460,404,377,332,269,225
70
C22 H18 N2 O9
58.15
3.99
6.17
58.00
4.11
6.04
463,419,384,334,246,228
59
C25 H26 N4 O7
60.72
5.30
11.33
60.80
5.34
11.25
400,383,349,291,254,226
63
C26 H28 N4 O7
61.41
5.55
11.02
61.44
5.60
11.00
397,354,323,277,235,222
Table 5. The major IR absorptions (cm-1) of carbonyl [1,3]oxazinan-4,6-dione (9-16).

No.
OHstr.
Phenol
NH2
C-H str.
benzylic
C=Ostr.
Lacton
C=Ostr.
Lactam
C=Nstr.
Imine
C=Cstr.
Aromatic
C-O str.
Lacton
CH bend.
Aromatic
9
10
11
12
13
14
15
16
3490
3495
3480
3475
-
3460,3410
3475,3400
-
3240
3220
3225
3240
3200
3240
3210
3210
1700
1680
1680
1675
1690
1670
1685
1670
1640
1650
1640
1655
1645
1635
1640
1650
1600
1620
1610
1610
1600
1600
1615
1600
1580
1590
1580
1575
1575
1580
1590
1570
1300
1310
1320
1320
1300
1310
1290
1290
770
760
760
780
760
760
780
770
Table 6. The major 1H NMR absorptions (ppm) of carbonyl [1,3] oxazinan-4,6-dione (9-16).
No.
9
10
11
12
13
14
15
16
NH2
5.7
5.8
-
October 2006
C
H2
3.20
3.12
3.22
3.15
3.11
3.20
3.17
3.18
C
H2
7.2
7.1
7.2
7.15
7.2
7.2
7.22
7.2
OH
4.8
4.75
4.9
4.8
4.8
4.75
4.8
4.85
H3C
2.7
2.77
2.75
2.68
2.78
2.84
2.75
2.75
CH3
H2
C C
H2 C O
2.46,2.5
2.44,2,5
Benzene
ring
6.4-7.5
6.5-7.5
6.44-7.7
6.4-7.5
6.4-7.8
6.4-7.5
6.4-7.5
6.5-7.4
33
absorption maxima (nm) of thiocarbonyl[1,3] oxazinan-4,6-dione (17-24).
No.
M.P/C
17
18
19
20
21
22
23
24
178-180
184-186
124-126
236-138
136-138
129-131
140-142
158-160
Yield
%
62
66
59
58
67
70
64
60
M.F.
Calc.
H%
3.79
3.81
5.15
5.70
3.53
3.86
5.13
4.87
C%
49.62
58.37
53.23
62.24
55.26
56.17
58.81
58.05
C11H10N2O4S
C18H14N2O5S
C13H15N3O3S
C22H24N4O3S
C21H16N2O8S
C22H18N2O8S
C25H26N4O6S
C24H24N4O6S
N%
10.52
7.56
14.32
13.20
6.14
5.95
10.97
11.28
C%
49.73
58.46
53.42
62.34
55.36
56.23
60.00
85.11
Found
H%
384
4.00
5.22
5.83
3.60
4.00
5.25
5.01
N%
10.45
7.34
14.20
13.11
6.04
5.91
1082
11.12
Maxima (nm)
425,367,291,249,220,203
436,402,286,255,231,223
389,352,320,284,247,227
403,387,355,321,285,224
430,386,361,342,288,234,222
410,379,346,275,249,226
416,390,361,282,237,229
400,369,345,289,264,235,220
Table 8. The major IR absorptions (cm-1) of thiocarbonyl [1,3]oxazinan-4,6-dione (17-24).

No.
17
18
19
20
21
22
23
24
OH str.
phenol
3500
3490
3495
3505
-
NH2
C-H str.
Benzylic
3310
3220
3200
3230
3200
3200
3210
3230
3480,3410
3495, 3420
-
C=O str.
Lacton
1685
1690
1680
1685
1670
1670
1685
1680
C=O str.
Lactam
1655
1650
1650
1640
1640
1640
1645
1650
C=N str.
Imine
1605
1605
1610
1620
1610
1600
1620
1625
C=C str.
Aromatic
1595
1590
1580
1570
1570
1655
1670
1675
C-O str.
Lacton
1290
1300
1310
1300
1320
1320
1310
1320
CH bend.
Aromatic
760
760
770
790
790
780
760
760
Table 9. The major 1H NMR absorptions (ppm) of thiocarbonyl [1,3] oxazinan-4,6-dione (17-24).
No.
17
18
19
20
21
22
23
24
-NH2
2.2
2.2
-
OH
C
H2
3.2
3.05
3.07
3.05
3.1
3.2
3.2
3.15
C
H2
7.2
7.15
7.2
7.11
7.05
7.15
7.2
7.2
4.9
4.9
4.8
4.8
-
H3C
2.66
2.65
2.7
2.65
CH3
O C
H2
C C
H2 C O
2.55
2.52
Benzene
ring
6.4-7.2
6.5-7.3
6.5-7.2
6.5-7.8
6.5-7.8
6.6-7.6
6.5-7.8
6.5-7.8
4. CALCULATION OF THE REACTION VELOCITY

A first-order reaction equation was applied to the reaction of Schiff-bases
with Malonic anhydride. It proves to be useful to calculation of the reactions
velocity under vaying temperatures (213-253)K with (10) K increase.
The value of the reaction velocity K was calculated for all reactions
by drawing the relation between ln At/A with time.
34
October 2006
The relation between lnK and 1/T was then drawn. It shows the
effect of temperature on the reaction velocity in order to obtain the ideal
temperature for the reaction. It was noticed that velocity increases with
temperature and that the velocity is stable at (353) k.
From the Tables (10-21) we notice that the values of H, S, and
G are positive. This proves that the reactions are endothermic and
spontaneous. We also notice that the activation energy H starts to
increase with different used compounds. So the (Ethylene Schiff-bases)
compounds are less than those of (thiourea schiff-bases), which are in
turn, less than the (Urea Schiff-bases) compounds. This is due to group
C=S and group C=O which reduce the electronic density on C=N group,
and consequently, it takes more energy and longer time for the reaction.
Table 10. Thermodynamic values for the reaction of (A) with malonic anhydride calculated from
the effect of temperature on K, Ea, H, S and G value (1).
T [K]
313
323
333
343
353
K,h-1
0.0413
0.0519
0.068
0.084
0.1112
Ea / J mol -1
3137.4
3137.4
3137.4
3137.4
3137.4
H Jmol-1
539.5
488.8
373.5
290.5
207.5
S J.K-1mol-1
-281.868
-282.366
-282.86
-283.362
-283.86
G K,mol-1
88764.16
91693.018
94565.88
131783.66
100410.08
Table 11. Thermodynamic values of reaction of (B) with malonic anhydride calculated from the
effect of temperature on K, Ea, H, S and G value (2).
T [K]
313
323
333
343
353
K,h-1
0.0533
0.0651
0.0891
0.1342
0.1831
Ea / J mol -1
3304.4043
3304.4043
3304.4043
3304.4043
3304.4043
H Jmol-1
706.504
623.504
540.504
457.504
374.504
S J.K-1mol-1
-283.86
-284.35
-284.939
-285.354
-285.935
G K,mol-1
89554.684
92468.554
95425.191
98333.926
101309.559
Table 12. Thermodynamic values of reaction of (C) with malonic anhydride calculated from the
T [K]
313
323
333
343
353
October 2006
K,h-1
0.0579
0.0691
0.0899
0.162
0.1997
Ea / J mol -1
3292.7345
3292.7345
3292.7345
3292.7345
3292.7345
H Jmol-1
694.8349
611. 8349
523. 8349
445. 8349
362. 8349
S J.K-1mol-1
-282.615
-284.441
-283.03
-283.528
-284.026
G K,mol-1
89153.3299
92486.2779
94772.8249
97695.9389
100624.0129
35
Table 13. Thermodynamic values of reaction of (D) with malonic anhydride calculated from the
T [K]
313
323
333
343
353
K,h-1
0.0521
0.0623
0.0711
0.0834
0.123
Ea / J mol -1
3322.8469
3322.8469
3322.8469
3322.8469
3322.8469
H Jmol-1
742.9469
641. 9469
558. 9469
475. 9469
392. 9469
S J.K-1mol-1
-284.026
-284.275
-285.105
-285.603
-286.018
G K,mol-1
89643.0849
92462.7719
95498.9119
98437.77
101357.3009
Table 14. Thermodynamic values of reaction of (E) with malonic anhydride calculated from the
T [K]
313
323
333
343
353
K,h-1
0.0031
0.0060
0.020
0.0332
0.0411
Ea / J mol -1
5710.4084
5710.4084
5710.4084
5710.4084
5710.4084
H Jmol-1
3112.5083
3029. 5083
2946. 5083
2863. 5083
2780. 5083
S J.K-1mol-1
-297.876
-280.042
-280.955
-281.453
-281.951
G K,mol-1
96347.6963
93483.0743
96504.5233
99401.8873
102309.2113
Table 15. Thermodynamic values of reaction of (F) with malonic anhydride calculated from the
T [K]
313
323
333
343
353
K,h-1
0.0037
0.0081
0.0301
0.0421
0.0562
Ea / J mol -1
5884.7083
5884.7083
5884.7083
5884.7083
5884.7083
H Jmol-1
3286.8083
3203. 8083
3120. 8083
3037. 8083
2954. 8083
S J.K-1mol-1
-281.785
-281.204
-281.702
-282.2
-282.615
G K,mol-1
91485.5133
94032.7003
96927.5743
99832.4083
102717.9033
Table 16. Thermodynamic values of reaction of (G) with malonic anhydride calculated
calculated from the effect of temperature on K, Ea, H, S and G value (19).
T [K]
313
323
333
343
353
K,h-1
0.0043
0.0076
0.0312
0.042
0.0558
Ea / J mol -1
5667.2566
5667.2566
5667.2566
5667.2566
5667.2566
H Jmol-1
3069.3566
2986. 3566
2903. 3566
2820. 3566
2737. 3566
S J.K-1mol-1
-280.125
-280.623
-281.121
-281.702
-282.117
G K,mol-1
90748.4816
93627.5856
96516.6496
99444.1426
102324.6576
Table 17. Thermodynamic values of reaction of (K) with malonic anhydride calculated from the
T [K]
313
323
333
343
353
36
K,h-1
0.0038
0.0068
0.0214
0.0396
0.0498
Ea / J mol -1
5730.3283
5730.3283
5730.3283
5730.3283
5730.3283
H Jmol-1
3132.4283
3049. 4283
2966. 4283
2883. 4283
2800. 4283
S J.K-1mol-1
-280.042
-280.623
-279.71
-281.619
-282.034
G K,mol-1
90785.5743
93690.229
96109.8583
99478.7453
102358.4303
October 2006
Table 18. Thermodynamic values of reaction of (L) with malonic anhydride calculated from the
T [K]
K,h-1
Ea / J mol -1
H Jmol-1
S J.K-1mol-1
G K,mol-1
313
0.0013
7924.8566
5326.9566
-279.129
92694.3336
323
0.0032
7924.8566
5243. 9566
-279.627
95563.4776
333
0.011
7924.8566
5160. 9566
-280.125
98442.5816
343
0.029
7924.8566
5077. 9566
-280.623
101331.6456
353
0.031
7924.8566
4994. 9566
-281.121
104230.669
Table 19. Thermodynamic values of reaction of (M) with malonic anhydride calculated from the
T [K]
K,h-1
Ea / J mol -1
H Jmol-1
S J.K-1mol-1
G K,mol-1
313
0.0018
7543.0566
4945.1566
-279.544
92442.4286
323
0.0041
7543.0566
4862. 1566
-280.042
95315.7226
333
0.018
7543.0566
4779. 1566
-280.623
98226.625
343
0.03
7543.0566
4696. 1566
-281.121
101263.0046
353
0.038
7543.0566
4613. 1566
-281.536
103995.3646
Table 20. Thermodynamic values of reaction of (N) with malonic anhydride calculated from the
T [K]
K,h-1
Ea / J mol -1
H Jmol-1
S J.K-1mol-1
G K,mol-1
313
0.0015
323
0.0033
8099.9866
5502.0866
-280.208
93207.1906
8099.9866
5419. 0866
-280.789
96113.9336
333
343
0.018
8099.9866
5336. 0866
-266.45
94063.9366
0.03
8099.9866
5253. 0866
-281.785
101905.3416
353
0.033
8099.9866
5170. 0866
-282.366
104845.2846
Table 21. Thermodynamic values of reaction of (O) with malonic anhydride calculated from the
T [K]
K,h-1
Ea / J mol -1
313
0.0016
323
0.0039
333
343
353
October 2006
H Jmol-1
S J.K-1mol-1
G K,mol-1
7834.1376
5236.2376
-280.208
92941.3416
7834.1376
5153. 2376
-280.457
95740.8486
0.019
7834.1376
5070. 2376
-280.955
98628.2526
0.032
7834.1376
4987. 2376
-281.536
101554.0856
0.038
7834.1376
4904. 2376
-281.951
104277.266
37
Figures 1, 2 and 3 show the reaction velocity for different compounds.

-1.6
Reaction of (A) with malonic anhydride
Reaction of (B) with Malonic anhydride
Reaction of (C) with Malonic anhydride
Reaction of (D) with Malonic anhydride
-1.8
-2.0
-2.2
ln K
-2.4
-2.6
-2.8
-3.0
-3.2
-3.4
0.0028
Y = -378.515 * X + 34.5918
R-squared = 0.976341
Y = -398.121 * X + 48.9335
Y = -396.715 * X + 48.7871
Y = -400.343 * X + 31.8692
0.0029
0.0030
0.0031
0.0032
1/T "Temperature"
0.0033
0.0034
Figure 1. The relationship between lnK and 1/T of reaction A,B,C and Dwith malonic anhydride.
-2.5
Reaction of (E) with Malonic anhydride
Reaction of (F) with Malonic anhydride
Reaction of (G) with Malonic anhydride
Reaction of (K) with malonic anhydride
-3.0
-3.5
ln K
-4.0
-4.5
-5.0
-5.5
Y = -682.802 * X + 113.334
Y = -690.401 * X + 114.623
Y = -688.001 * X + 114.056
R-squared = 0.9425
Y = -709.001 * X + 117.956
-6.0
0.0028
0.0029
0.0030
0.0031
0.0032
1/T "Temperature"
0.0033
0.0034
Figure 2. The relationship between lnK and 1/T of reaction E,F,G and K with malonic anhydride.
38
October 2006
-2.5
Reaction of (L) with Malonic anhydride
Reaction of (M) with Malonic anhydride
-3.0
Reaction of (N) with malonic anhydride

Reaction of (O) with Malonic anhydride
-3.5
-4.0
ln K
-4.5
-5.0
-5.5
-6.0
-6.5
Y = -954.802 * X + 142.244
Y = -908.802 * X + 134.554
Y = -978.902 * X + 146.581
Y = -943.872 * X + 140.585
-7.0
0.0028
0.0029
0.0030
0.0031
1/T "Temperature"
0.0032
0.0033
Figure 3. The relationship between lnK and 1/T of reaction L,M,N and O with malonic anhydride.
5. CONCLUSIONS
1-The Schiff bases prepared in this research were verified by
elemental analysis, IR, 1H NMR and UV-Visible spectra.
2-The Oxazinans prepared in this research were verified by
elemental analysis, IR,1H NMR and UV-Visible spectra.
3- A first-order reaction equation was applied to the reaction of
Schiff-bases with malonic anhydride. It proves to be useful for the
calculation of the reactions velocity under varying temperatures (213253)K with (10) K increase.
4- The values of H, S, and G are positive. This proves that the
reactions are endothermic and spontaneous.
5- The (Ethylene Schiff-bases) compounds are needs less energy than
those of (Thiourea schiff-bases), which are in turn, less energy than the
October 2006
39
(Urea Schiff-bases) compounds. This is due to group C=S and group C=O
which reduce the electronic density on C=N group, and consequently, it
needs more energy and takes longer time for the reaction.
Table 22. The Schiff bases prepared in this research.
Reaction No.
Compound Name
Structure
(Z)
2-[(2-amino-ethylimino)-methyl]-phenol
HO
N
NH2
(Z)
2-({2-[(2-hydroxy-benzylidene)-amino]ethylimino}-methyl)-phenol
OH
N
HO
(Z)
(Z)
N,N-(3-dimethylamino-benzylidene)-ethane-1,2diamine
H2N
D
E
N-(4-dimethylamino-benzylidene)-N'-(4dimethylamino-benzylidene)-ethane-1,2 -diamine
(Z)
N
N
N
N
(Z)
(2-hydroxy-benzylidene)-thiourea
NH2
HO
(Z)
( E)
1,3-bis-(2-hydroxy-benzylidene)-thiourea
N
S
N
OH
OH
( Z)
(Z)
(4-dimethylamino-benzylidene)-thiourea
1,3-bis-(4-dimethylamino-benzylidene)-thiourea
N
H 2N
N
(Z)
N
S
N
(Z)
(2-hydroxy-benzylidene)-urea
NH2
HO
(Z)
(E)
1,3-bis-(2-hydroxy-benzylidene)-urea
N
O
N
OH
OH
(Z)
(Z)
(4-dimethylamino-benzylidene)-urea
1,3-bis-(4-dimethylamino-benzylidene)-urea
N
H2N
N
N
(Z)
N
O
N
(Z)
40
October 2006
Table 23. The oxazinanes prepared in this research.

No
Name
3-(2-Amino-ethyl)-2-(2-hydroxyphenyl)-[1,3]oxazinane-4,6-dione
Structure
HO
O
O
3-{2-[(2-Hydroxy-benzylidene)-amino]ethyl}-2-(2-hydroxy-phenyl)-[1,3]
oxazinane-4,6-dione
3-(2-Amino-ethyl)-2-(4-dimethylami
no-phenyl)-[1,3]oxazinane-4,6-dione
3-(2-Amino-ethyl)-2-(4-dimethylami
no-phenyl)-[1,3]oxazinane-4,6-dione
NH2
N
O
O
N
HO
OH
(Z)
NH2
O
HO
O
O
N
O
OH
O
O
3-(2-Amino-ethyl)-2-(2-hydroxy-phenyl
)-[1,3]oxazinane-4,6-dione
O
O
N
N
(Z)
2-(4-dimethylamino-phenyl)-3-{2-[2-(4-dimethy lamino-phenyl)4,6-dioxo-[1,3]oxazinan-3-yl] -ethyl}-[1,3]oxazinane-4,6-dione
2-(2-Hydroxy-phenyl)-3-{2-[2-(2-hydroxyphenyl)-4,6-dioxo-[1,3]oxazinan-3-yl]
-ethyl}-[1,3]oxazepane-4,7-dione
HO
O
O
OH
2-(4-Dimethylamino-phenyl)-3-{2-[2-(4-dimethyl
amino-phenyl)-4,6-dioxo-[1,3]oxazinan-3-yl]ethyl}-[1,3]oxazepane-4,7-dione
2-(2-Hydroxy-phenyl)-4,6-dioxo
-[1,3]oxazinane-3-carboxylic
acid amide
October 2006
HO
O
O
N
O
NH2
N
O
41
Table 23. Continued.

No
Name
10
2-(2-Hydroxy-phenyl)-4,6-dioxo[1,3]oxazinane-3-carboxylic acid
2-hydroxy-benzylideneamide
11
12
13
14
Structure
HO
2-(2-Hydroxy-phenyl)-3-[2-(2-hydroxyphenyl)-4,6-dioxo-[1,3]oxazinane-3carbonyl]-[1,3]oxazinan-4,6-dione
2-(2-Hydroxy-phenyl)-3-[2-(2-hydroxyphenyl)-4,6-dioxo-[1,3]oxazinane-3carbonyl]-[1,3]oxazepane-4,7-dione
(E)
O HO
2-(4-Dimethylamino-phenyl)-4,6-dioxo
-[1,3]oxazinane-3-carboxylic acid
amide
2-(4-Dimethylamino-phenyl)-4,6-dioxo[1,3]oxazinane-3-carboxylic acid -4dimethylamino-benzylideneamide
O
O
H2 N
O
N
O
O
O
O
N
N (E)
N
HO
OH
O O
HO
O
OH
N
2-(4-dimethylamino-phenyl)-3-[2-(4-Dimethyl
amino-phenyl)-4,6-dioxo-[1,3]oxazinane-3carbonyl]-[1,3]oxazinan-4,6-dione
O O
15
O
O
O O
16
2-(4-Dimethylamino-phenyl)-3-[2-(4-dimethyl
amino-phenyl)-4,6-dioxo-[1,3]oxazinane-3carbonyl]-[1,3]oxazepane-4,7-dione
O
O
17
2-(2-Hydroxy-phenyl)-4,6-dioxo-[1,3]
oxazinane-3-carbothioic acid amide
O O
2-(2-Hydroxy-phenyl)-4,6-dioxo-[1,3
]oxazinane-3-carbothioic acid
2-hydroxy-benzylideneamide
42
S
O
NH2
O
HO
HO
18
N (E)
O HO
October 2006
Table 23. Continued.

No
19
20
21
Name
2-(4-Dimethylamino-phenyl)-4,6-diox
o-[1,3]oxazinane-3-carbothioic acid
amide
2-(4-Dimethylamino-phenyl)-4,6dioxo- [1,3]oxazinane-3-carbothioic acid
4-dimethylamino-benzylideneamide
2-(2-Hydroxy-phenyl)-3-[2-(2-hydroxy-phenyl)
-4,6-dioxo-[1,3]oxazinane-3-thiocarbonyl]
-[1,3]oxazinan-4,6-dione
Structure
S
H 2N
O
O
N
N
O
N
(E)
HO
OH
O
O
O O
22
2-(2-Hydroxy-phenyl)-3-[2-(2-hydroxy-p
henyl)-4,6-dioxo-[1,3]oxazinane-3thiocarbonyl]-[1,3]oxazepane-4,7-dione
HO
O
S
N
OH
N O
O O
23
2-(4-dimethylamino-phenyl)-3-[2-(4-Dimeth
ylamino-phenyl)-4,6-dioxo-[1,3]oxazinane
-3-thiocarbonyl]-[1,3]oxazinan-4,6-dione
O
O
S
N
O
O
O O
N
24
2-(4-Dimethylamino-phenyl)-3-[2-(4-dimeth
ylamino-phenyl)-4,6-dioxo-[1,3]oxazinane-3
- thiocarbonyl]-[1,3]oxazepane-4,7-dione
N
S
O
O
O O
O
O
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SYNTHESIS, CHARACTERIZATION AND KINETIC

STUDIES OF ETHYLENE-[1,3]OXAZINAN -4,6DIONE, CARBONYL-[1,3]OXAZINAN-4,6-DIONE AND

N-benzylidene2-({2-[(2-hydroxy-benzylidene)-amino]-ethylimino}-methyl)phenol,1,3-Bis-(2-hydroxy-benzylidene)-urea and1,3-Bis-(2-hydroxy-benzylidene)Thiourea (Schiff bases) were prepared by condensation of Ethylene

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

--2)- - 64- - [-3- [ 31]1- -64-(-

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

The reaction of N-benzylidene 1,5-dimethyl-2-phenylpyrazolonamines

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

band at (1670-1685) cm-1 and (-NH2) absorption bands at (3400,3650)

water bath/ reflx

This is indicated by the appearance of the characteristic C=O

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

The new absorption bands of the (C=O) group in the IR spectra of

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Table 2. The major IR absorptions (cm-1) of ethylene [1,3]oxazinan-4,6-dione (1-8).

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

Table 5. The major IR absorptions (cm-1) of carbonyl [1,3]oxazinan-4,6-dione (9-16).

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Table 8. The major IR absorptions (cm-1) of thiocarbonyl [1,3]oxazinan-4,6-dione (17-24).

4. CALCULATION OF THE REACTION VELOCITY

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Figures 1, 2 and 3 show the reaction velocity for different compounds.

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

Reaction of (N) with malonic anhydride

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

Table 23. The oxazinanes prepared in this research.

2-(4-dimethylamino-phenyl)-3-{2-[2-(4-dimethy lamino-phenyl)4,6-dioxo-[1,3]oxazinan-3-yl] -ethyl}-[1,3]oxazinane-4,6-dione

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Table 23. Continued.

2-(4-Dimethylamino-phenyl)-4,6-dioxo[1,3]oxazinane-3-carboxylic acid -4dimethylamino-benzylideneamide

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

Table 23. Continued.

A.I. Mayer, Hetrocycles in organic systeme, John-Wiley and Sons,

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

J. Macmillan, S.Washburen, Synthesis of 2- phenyl -1,3-oxazepine

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

Mohammed A. Al-Hadithi (25- 45)

University of Sharjah Journal of Pure & Applied Sciences Volume 3, No. 3

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