Synthesis of some novel 2-arylidene thiazoloquinazolinone derivatives via one-pot, three-component reaction

Article abstract of DOI:10.1080/10426507.2010.503210

A one-pot, multicomponent reaction of thioxoquinazolinone with ethyl chloroacetate and aromatic aldehydes is described for the preparation of novel thiazoloquinazolinone derivatives using sodium hydride in ethanol under reflux conditions. The structures of all synthesized compounds were identified by IR, ¹H NMR, ¹³C NMR, and elemental analysis data. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426507.2010.503210

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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Synthesis of Some Novel 2-Arylidene
Thiazoloquinazolinone Derivatives via
One-Pot, Three-Component Reaction
A. Mobinikhaledi a , N. Foroughifar a b , S. Ebrahimi c , F. Rahimi a &
F. Zandi b
a Department of Chemistry , Arak University , Arak, Iran
b Faculty of Chemistry , Islamic Azad University , North Tehran
Branch, North Tehran, Iran
c Department of Chemistry , Islamic Azad University , Malayer
Branch, Malayer, Iran
Published online: 07 Mar 2011.
To cite this article: A. Mobinikhaledi , N. Foroughifar , S. Ebrahimi , F. Rahimi & F. Zandi (2011)
Synthesis of Some Novel 2-Arylidene Thiazoloquinazolinone Derivatives via One-Pot, Three-
Component Reaction, Phosphorus, Sulfur, and Silicon and the Related Elements, 186:3, 457-463, DOI:
10.1080/10426507.2010.503210
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Phosphorus, Sulfur, and Silicon, 186:457–463, 2011
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2010.503210
SYNTHESIS OF SOME NOVEL 2-ARYLIDENE
THIAZOLOQUINAZOLINONE DERIVATIVES VIA ONE-POT,
THREE-COMPONENT REACTION
A. Mobinikhaledi,1 N. Foroughifar,1,2 S. Ebrahimi,3 F. Rahimi,1
and F. Zandi2
1Department of Chemistry, Arak University, Arak, Iran
2Faculty of Chemistry, Islamic Azad University, North Tehran Branch,
North Tehran, Iran
3Department of Chemistry, Islamic Azad University, Malayer Branch,
Malayer, Iran
GRAPHICAL ABSTRACT
X
X
O
CHO
O
O
N
NaH
NH Cl COOEt
+
+
N
S
Y
N
S
H
Y
Abstract A one-pot, multicomponent reaction of thioxoquinazolinone with ethyl chloroacetate
and aromatic aldehydes is described for the preparation of novel thiazoloquinazolinone deriva-
tives using sodium hydride in ethanol under reflux conditions. The structures of all synthesized
compounds were identified by IR, 1H NMR, 13C NMR, and elemental analysis data.
Keywords Multicomponent reaction; quinazolinone; thiazoloquinazolinone
INTRODUCTION
Multicomponent reactions (MCRs), in which three or more easily accessible compo-
nents react to form a single product, are some of the most important reactions in organic
synthesis.1,2 MCRs are a promising field of chemistry because the synthesis of complicated
molecules can be achieved in a very fast, efficient, and time-saving manner without the
isolation of any intermediate.3 MCRs are particularly useful to generate diverse chemical
libraries of drug-like compounds with biological interest.4,5 MCRs can provide products
Received 28 April 2010; accepted 16 June 2010.
We gratefully acknowledge the financial support from the Research Council of Arak University.
Address correspondence to A. Mobinikhaledi, Department of Chemistry, Arak University, Arak 38156-879,
Iran. E-mail: akbar mobinikhaledi@yahoo.com
457

458
A. MOBINIKHALEDI ET AL.
with the diversity needed for the discovery of new compounds or modification using com-
binatorial chemistry methods.6–8 The search and discovery for new MCRs on one hand,9
and the full exploitation of already known multicomponent reactions on the other hand, are
therefore currently of considerable interest.
The chemistry of thiazolidin-4-one ring systems is of considerable interest as a core
structure in various synthetic pharmaceuticals displaying a broad spectrum of biologi-
cal activities.10–12 A literature survey reveals that quinazoline derivatives have attracted
considerable attention in recent years due to their potential antibacterial activity.12 Here,
due to versatile biological activities of quinazoline, and as a continuation of our research
program on the synthesis of thioxoquinazoline derivatives and MCRs,13–18 we have made
an attempt to synthesize some novel thiazoloquinazolinone derivatives in good yield via
cyclocondensation reactions.
RESULTS AND DISCUSSION
In the present study, we report our results on a new type of multicomponent reaction
where three organic components react to form novel compounds. The starting thioxoquina-
zolinones 1a–d were synthesized by the reaction of 5,5-dimethylcyclohexane-1,3-dion
(dimedone) and the corresponding aromatic aldehyde with thiourea in the presence of a
catalytic amount of silica sulfuric acid (SSA).19 Further reaction of compounds 1a–d with
aromatic aldehydes 3a–e and ethyl chloroacetate 2 in the presence of sodium hydride in
refluxing ethanol afforded the corresponding thiazoloquinazolinone derivatives 4a–k, as
shown in Scheme 1.
X
X
O
CHO
O
O
N
NaH
NH Cl COOEt
+
+
N
S
Y
N
S
H
Y
1a-d
2
3a-e
4a-k
Scheme 1
The reaction conditions between thioxoquinazolinone 1a, ethyl chloroacetate 2, ben-
zaldehyde 3a, and different bases in absolute ethanol were examined (Table 1). Reaction of
Table 1 Optimization of condition for the synthesis of compound 4a
Entry
Base
Ratio 1a:base
Yields (%)
1
2
3
4
5
6
7
8
9
NaOAc
NaOAc
NaOH
NaOH
NaOH
Pyridine
NaH
1:1
1:2
1:1
1:1.5
1:2
1:1
1:1
1:1.5
1:2
10
15
15
16
21
<5
40
56
57
NaH
NaH

NOVEL 2-ARYLIDENE THIAZOLOQUINAZOLINONE DERIVATIVES
459
Table 2 Synthesis
of
(Z)-2-arylidene-8,8-dimethyl-5-aryl-8,9-dihydro-2H-thiazolo[2,3-b]quinazoline-
3,6(5H,7H)-dione derivatives 4a–k
Entry
X
Y
Mp (◦C)
Time (h)
Yields
4a
4b
4c
4d
4e
4f
4g
4h
4i
H
H
4-Me
4-Me
4-Me
4-Me
4-Cl
4-Cl
H
4-Me
H
4-Me
4-Cl
4-NO2
H
4-Me
H
255–257
246–247
215–217
226–227
241–242
242–243
236–237
259–260
193–195
188–189
183–184
9
10
9
10
8
56
50
55
50
70
65
55
62
55
65
60
8
10
11
10
9
3,4-OMe
3,4-OMe
3,4-OMe
4j
4k
4-Cl
4-OMe
10
compound 1a (1.0 equiv) with 1.0 equiv of benzaldehyde 3a, 1.0 equiv of ethyl chloroac-
etate, and 1.0 equiv of NaOAc in ethanol gave the desired product 4a in 10% yield (Table
1, entry 1). For optimizing the reaction conditions, different bases and ratios of bases were
compared. With the optimized conditions in hand, the scope of the reaction was investigated,
and the typical results were summarized in Table 1.
To evaluate the generality of the process, several examples illustrating the present
procedure for the synthesis of thiazoloquinazolinone derivatives 4 were studied (Table 2).
The reaction of compound 1a–d with various aromatic aldehydes 3a–e bearing electron-
withdrawing groups (such as nitro and halo), electron-releasing groups (such as methyl and
methoxy), and ethyl chloroacetate 2 was carried out in the presence of sodium hydride,
and it afforded the corresponding products in good yields. On the other hand, aliphatic
aldehydes such as propionaldehyde or butyraldehyde and heterocyclic aldehydes such as
2-pyridinecarbaldehyde or furfural were also examined under the same conditions, but the
corresponding products were isolated only in trace amounts.
Two isomeric products may be expected for this reaction. The Z configuration of the
exocyclic C C bond, in the 2-benzylidene derivatives 4a–k, was attributed on the basis of
1H NMR spectral analysis. The methine proton resonated, as expected, at higher chemical
shift values, due to the deshielding effect of the adjacent C O, than it would do in E
isomers, because of the lower deshielding effect of 1-S.20,21
1H NMR spectra of all synthesized compounds reveal a singlet signal at low field shift
due to the resonance of the vinyl proton. The aliphatic protons relative to the pyrimidine
ring appear at δ 6.20. The IR spectra of compounds 4a–k show absorptions at 1700 and
1650 cm−1, characteristic of the carbonyl group.
CONCLUSION
In conclusion, we have described a simple, efficient, and one-pot synthesis for prepa-
ration of thiazoloquinazolinone derivatives in three-component condensation reactions of
aldehydes, ethyl chloroacetate, and thioxoquinazolinone in present NaH. In addition to the
efficiency and simplicity provided, this protocol describes good yields of cyclization and
simple purification for these products.

460
A. MOBINIKHALEDI ET AL.
EXPRIMENTAL
Melting points were determined using an electrothermal digital melting point ap-
paratus and are uncorrected. IR spectra were prepared on a galaxy series FT-IR 5000
spectrophotometer using KBr discs. NMR spectra were recorded on a Brucker spectropho-
tometer (300 MHz) in CDCl3 using TMS as an internal standard. Elemental analyses were
performed by Vario EL equipment at Arak University.
General Procedure for Preparation of 4a–k
A solution of thioxoquinazolinone 1a-d (0.2 mmol), sodium hydride (0.3 mmol),
ethyl chloroacetate (0.3 mmol), and the appropriate aromatic aldehyde 3a–e (0.2 mmol) in
ethanol (10 mL) was refluxed for a predetermined time. The progress of the reaction was
monitored by TLC. The reaction mixture was cooled to give a precipitate, which was then
filtered and washed with cold ethanol. The compound obtained was dried and crystallized
from ethanol, giving the pure products 4a–k.
(Z)-2-Benzylidene-8,8-dimethyl-5-phenyl-8,9-dihydro-2H-
thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4a
FT-IR (KBr): v = 3055 (CHarom.), 2868 (CHaliph.), 1712 (C O), 1658 (C O), 1548
(C N) cm−1; 1H NMR (CDCl3): δ = 1.04 (s, 3H, CH3), 1.13 (s, 3H, CH3), 2.24 (d, J =
16.3 Hz, 1H, CH2 C C), 2.31(d, J = 16.5 Hz, 1H, CH2 C C), 2.58 (d, J = 18.0 Hz, 1H,
CH2 C O), 2.67 (d, J = 18.2 Hz, 1H, CH2 C O), 6.24 (s, 1H, HPyrimidine), 7.24–7.33
(m, 3H, Harom.), 7.42–7.78 (m, 7H, Harom.), 7.80 (s, 1H, Hvinyl); 13C NMR (CDCl3): δ =
27.8 (CH3), 29.0 (CH), 44.8 (CH2), 50.9 (CH2), 53.9 (C-5), 115.2, 119.5, 127.8, 128.6,
128.7, 129.3, 130.2, 130.8, 133.0, 134.6, 140.0, 155.6, 159.7 (C N), 165.0 (N C O),
195.9 (C O); C25H22N2O2S: C, 72.44; H, 5.35; N, 6.76; S, 7.74. Found: C, 72.29; H, 5.22;
N, 6.60; S, 7.68.
(Z)-8,8-Dimethyl-2-(4-methylbenzylidene)-5-phenyl-8,9-dihydro-2H-
thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4b
FT-IR (KBr): v = 2866 (CHarom.), 1710 (C O), 1656 (C O), 1550 (C N) cm−1
;
1H NMR (CDCl3) δ = 1.04 (s, 3H, CH3), 1.13 (s, 3H, CH3), 2.24 (d, J = 16.4 Hz, 1H,
CH2 C C), 2.31 (d, J = 16.3 Hz, 1H, CH2 C C), 2.42 (s, 3H, CH3), 2.59 (d, J = 18.2
Hz, 1H, CH2 C O), 2.68 (d, J = 18.1 Hz, 1H, CH2 C O), 6.24 (s, 1H, HPyrimidine),
7.27–7.45 (m, 9H, H arom.), 7.81 (s, 1H, H vinyl); 13C NMR (CDCl3 6): δ = 21.7 (CH3), 27.7
(CH3), 29.0 (CH3), 32.7(CH), 45.0 (CH2), 50.9 (CH2), 53.8 (C-5), 115.1, 118.4, 127.3,
128.6, 128.7, 130.1, 130.2, 134.4, 139.9, 141.6, 156.1 (C N), 159.6, 165.2 (N C O),
195.9 (C O); C26H24N2O2S: C, 72.87; H, 5.64; N, 6.54; S, 7.48. Found: C, 72.61; H, 5.55;
N, 6.42; S, 7.39.
(Z)-2-Benzylidene-8,8-dimethyl-5-p-tolyl-8,9-dihydro-2H-
thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4c
FT-IR (KBr): v = 3047 (CHarom.), 2955 (CHaliph.), 1716 (C O),1656 (C O), 1547
1
(C N) cm−1; H NMR (CDCl3) δ = 1.06 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.28 (s,
3H, CH3), 2.30 (s, 2H, CH2 C C), 2.62 (d, J = 17.9 Hz, 1H, CH2 C O), 2.72 (d,

NOVEL 2-ARYLIDENE THIAZOLOQUINAZOLINONE DERIVATIVES
461
J = 18.1 Hz, 1H, CH2 C O), 6.23 (s, 1H, HPyrimidine), 7.11–7.15 (m, 2H, H arom.), 7.33 (d,
J = 7.7 Hz, 2H, Harom.), 7.50 (s, 5H, Harom.), 7.84 (s, 1H, H vinyl); 13C NMR (CDCl3): δ =
21.2 (CH3), 27.7 (CH3), 29.0 (CH3), 32.8(CH), 44.7 (CH2), 50.9(CH2), 53.7 (C-5), 115.2,
119.6, 127.7, 129.3, 130.1, 130.8, 133.0, 134.5, 136.8, 138.2, 153.6, 159.6 (C N), 165.1
(N C O), 195.9 (C O); C26H24N2O2S: C, 72.87; H, 5.64; N, 6.54; S, 7.48. Found: C,
72.71; H, 5.59; N, 6.48; S, 7.36.
(Z)-8,8-Dimethyl-2-(4-methylbenzylidene)-5-p-tolyl-8,9-dihydro-
2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4d
FT-IR (KBr): v = 3038 (CHarom.), 2966 (CHaliph.), 1710 (C O),1651(C O), 1539
1
(C N) cm−1; H NMR (CDCl3): δ = 1.05 (s, 3H, CH3), 1.13 (s, 3H, CH3), 2.29 (s, 5H,
CH2 C C and CH3), 2.42 (s, 3H, CH3), 2.63 (s, 2H, CH2 C O), 6.20 (s, 1H, HPyrimidine),
7.12 (d, J = 6.6 Hz, 2H, H arom.), 7.28–7.34 (m, 4H, H arom.), 7.39 (d, J = 6.9 Hz, 2H,
H arom.), 7.77 (s, 1H, H vinyl); 13C NMR (CDCl3): δ = 21.2 (CH3), 21.7 (CH3), 27.7 (CH3),
29.0 (CH3), 32.8 (CH), 44.5 (CH2), 50.9 (CH2), 53.7 (C-5), 115.1, 118.1, 127.7, 129.4,
130.1, 130.3, 135.2, 136.7, 138.6, 141.8, 155.0, 160.1 (C N), 165.0 (N C O), 195.8
(C O); C27H26N2O2S: C, 73.27; H, 5.92; N, 6.33; S, 7.25. Found: C, 73.11; H, 5.80; N,
6.26; S, 7.19.
(Z)-2-(4-Chlorobenzylidene)-8,8-dimethyl-5-p-tolyl-8,9-dihydro-
2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4e
FT-IR (KBr): v = 3040 (CHarom.), 2939–2866 (CHaliph.), 1710 (C O),1651(C O),
1548 (C N) cm−1; 1H NMR (CDCl3): δ = 1.06 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.22–2.34
(m, 5H, CH2 C C and CH3), 2.61 (d, J = 18.1 Hz, 1H, CH2 C O), 2.70 (d, J = 18.0
Hz, 1H, CH2 C O), 6.21 (s, 1H, HPyrimidine), 7.10–7.14 (m, 2H, Harom.), 7.32 (d, J = 7.9
Hz, 2H, H arom.), 7.42 (d, J = 8.8 Hz, 2H, Harom.), 7.47 (d, J = 8.8 Hz, 2H, H arom.), 7.60
(s, 1H, Hvinyl). 13C NMR (CDCl3): δ = 21.2 (CH3), 27.7 (CH3), 29.3 (CH3), 32.7 (CH),
44.8 (CH2), 50.9 (CH2), 53.8 (C-5), 115.3, 120.4, 128.9, 129.4, 129.6, 131.2, 131.6, 132.6,
136.7, 136.8, 138.5, 155.6, 158.8 (C N), 164.9 (N C O), 195.9 (C O); Anal.calcd for
C26H23ClN2O2S: C, 67.45; H, 5.01; N, 6.05; S, 6.93. Found: C, 67.20; H, 4.87; N, 5.92; S,
6.81.
(Z)-8,8-Dimethyl-2-(4-nitrobenzylidene)-5-p-tolyl-8,9-dihydro-2H-
thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4f
FT-IR (KBr): v = 3033 (CHarom.), 2962–2868 (CHaliph.), 1714 (C O),1647 (C O),
1554 (C N) cm−1; 1H NMR (CDCl3): δ = 1.06 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.29 (b,
2H, CH2 C C), 2.30 (s, 3H, CH3), 2.60 (d, J = 18.4 Hz, 1H, CH2 C O), 2.70 (d, J =
18.4 Hz, 1H, CH2 C O), 6.21 (s, 1H, HPyrimidine), 7.13 (t, J = 6.5 Hz, 2H, Harom.), 7.32
(d, J = 7.8 Hz, 2H, Harom.), 7.65 (d, J = 8.4 Hz, 2H, Harom.), 7.80 (s, 1H, Hvinyl), 8.34
(d, J = 8.4 Hz, 2H, Harom.). 13C NMR (CDCl3): δ = 21.2 (CH3), 27.7 (CH3), 29.0 (CH3),
32.8 (CH), 44.5 (CH2), 50.9 (CH2), 54.0 (C-5), 115.6, 124.3, 124.5, 127.7, 129.5, 130.5,
130.9, 136.3, 138.8, 139.1, 148.0, 154.9, 158.1 (C N), 164.4 (N C O), 195.9 (C O);
Anal.calcd for C26H23N3O4S: C, 65.94; H, 4.90; N, 8.87; S, 6.77. Found: C, 65.68; H, 4.79;
N, 8.68; S, 6.51.

462
A. MOBINIKHALEDI ET AL.
(Z)-2-Benzylidene-5-(4-chlorophenyl)-8,8-dimethyl-8,9-
dihydro-2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4g
FT-IR (KBr): v = 3051 (CHarom.), 2868 (CHaliph.), 1714 (C O),1658 (C O), 1539
(C N) cm−1; 1H NMR (CDCl3): δ = 1.05 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.25 (d, J =
16.9 Hz, 1H, CH2 C C), 2.32 (d, J = 17.2 Hz, 1H, CH2 C C), 2.56–2.70 (m, 2H,
CH2 C O), 6.21 (s,1H, HPyrimidine), 7.29 (d, J = 8.7 Hz, 2H, Harom.), 7.38 (d, J = 7.9 Hz,
2H, Harom.), 7.50 (s, 5H, Harom.), 7.83 (s,1H, Hvinyl); 13C NMR (CDCl3): δ = 27.7 (CH3),
29.1 (CH3), 32.7 (CH), 44.8 (CH2), 50.8 (CH2), 53.3 (C-5), 114.8, 119.4, 128.9, 129.1,
129.3, 130.2, 130.8, 132.9, 134.5, 134.7, 138.3, 156.0, 159.5 (C N), 165.0 (N C O),
195.8 (C O); Anal.calcd for C25H21ClN2O2S: C, 66.88; H, 4.71; N, 6.24; S, 7.14. Found:
C, 66.64; H, 4.62; N, 6.03; S, 6.98.
(Z)-5-(4-Chlorophenyl)-8,8-dimethyl-2-(4-methylbenzylidene)-8,9-
dihydro-2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4h
FT-IR (KBr): v = 3040 (CHarom.), 2955–2854 (CHaliph.), 1710 (C O),1649 (C O),
1539 (C N) cm−1; 1H NMR (CDCl3): δ = 1.04 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.24 (d,
J = 16.6 Hz,1H, CH2 C C), 2.31 (d, J = 15.4 Hz, 1H, CH2 C C), 2.43 (s, 3H, CH3),
2.60 (d, J = 18.1 Hz, 1H CH2 C O), 2.68(d, J = 18.2 Hz, 1H, CH2 C O), 6.20 (s,
1H, HPyrimidine), 7.21–7.43 (m, 8H, H arom.), 7.80 (s,1H, H vinyl); 13C NMR (CDCl3): δ =
21.7 (CH3), 27.7 (CH3), 29.0 (CH3), 32.8 (CH), 44.8 (CH2), 50.8 (CH2), 53.3 (C-5), 114.6,
118.0, 128.9, 129.1, 129.3, 130.1, 130.3, 134.4, 135.0, 138.4, 141.8, 156.1, 159.7 (C N),
165.1 (N C O), 195.9 (C O); Anal.calcd for C26H23ClN2O2S: C, 67.45; H, 5.01; N,
6.05; S, 6.93. Found: C, 67.22; H, 4.88; N, 5.84; S, 6.72.
(Z)-2-Benzylidene-5-(3,4-dimethoxyphenyl)-8,8-dimethyl-8,9-dihydro-
2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4i
FT-IR (KBr): v = 3044 (CHarom.), 2957–2872 (CHaliph.), 1716 (C O), 1662 (C O),
1
1533 (C N) cm−1; H NMR (CDCl3): δ = 1.07 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.25
(d, J = 18 Hz, 1H, CH2 C C), 2.32 (d, J = 18 Hz, 1H, CH2 C C), 2.58 (d, J = 18.0
Hz, 1H, CH2 C O), 2.66 (d, J = 17.8 Hz, 1H, CH2 C O), 3.83 (s, 3H, OCH3), 3.89
(s, 3H, OCH3), 6.19 (s, 1H, HPyrimidine), 6.79 (d, J = 8 Hz, 1H, Harom.), 6.9 4 (d, J = 8.2
Hz, 1H, Harom.), 7.01 (s, 1H, H arom.), 7.49 (t, 5H, Harom.), 7.81 (s, 1H, H vinyl) . 13C NMR
(CDCl3): δ = 27.6 (CH3), 29.1 (CH3), 32.8 (CH), 44.4 (CH2), 50.9 (CH2), 53.6 (C-5), 55.8
(OMe), 55.9 (OMe), 111.0, 111.3, 115.1, 119.3, 119.9, 129.4, 130.2, 130.9, 132.21, 132.9,
134.9, 148.9, 149.2, 155.2, 159.8 (C N), 165.0 (N C O), 195.9 (C O); Anal.calcd for
C27H26N2O4S: C, 68.33; H, 5.52; N, 5.90; S, 6.76. Found C, 68.09; H, 5.41; N, 5.74; S,
6.59.
(Z)- 2-(4-Chlorobenzylidene)-5-(3,4-dimethoxyphenyl)-8,8-
dimethyl-8,9-dihydro-2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4j
FT-IR (KBr): v = 3049 (CH arom.), 2931 (CH aliph.), 1716 (C O),1649 (C O), 1533
(C N) cm−1; 1H NMR (CDCl3): δ = 1.07 (s, 3H, CH3), 1.13 (s, 3H, CH3), 2.25 (d, J =
15 Hz, 1H, CH2 C C), 2.31 (d, J = 15 Hz, 1H, CH2 C C), 2.57(d, J = 18 Hz, 1H,
CH2 C O), 2.66 (d, J = 18 Hz, 1H, CH2 C O), 3.83 (s, 3H, OCH3), 3.88 (s, 3H,
OCH3), 6.18 (s, 1H, CHPyrimidine), 6.78 (d, J = 8.3 Hz, 1H, Harom.), 6.93 (d, d, j = 8.3, 1.7
Hz, 1H, Harom.), 7.01 (d, J = 1.6 Hz, 1H, Harom.), 7.41 (d, J = 8.7 Hz, 2H, Harom.), 7.46

NOVEL 2-ARYLIDENE THIAZOLOQUINAZOLINONE DERIVATIVES
463
(d, J = 8.6 Hz, 2H, Harom.), 7.74 (s,1H, Hvinyl); 13C NMR (CDCl3): δ = 27.6 (CH3), 29.1
(CH3), 32.7 (CH), 44.8 (CH2), 50.8 (CH2), 53.6 (C-5), 55.8 (OMe), 55.9 (OMe), 110.9,
111.3, 115.2, 119.9, 120.3, 129.6, 131.2, 131.5, 132.3, 132.7, 136.7, 148.8, 149.2, 155.7,
158.8(C N), 164.9 (N C O), 196.0 (C O); Anal.calcd for C27H25ClN2O4S: C, 63.71;
H, 4.95; N, 5.50; S, 6.30. Found: C, 63.50; H, 4.86; N, 5.38; S, 6.14.
(Z)-5-(3,4-Dimethoxyphenyl)-2-(4-methoxybenzylidene)-8,8-
dimethyl-8,9-dihydro-2H-thiazolo[2,3-b]quinazoline-3,6(5H,7H)-dione 4k
FT-IR (KBr): v = 3033 (CHarom.), 2931–2835 (CHaliph.), 1707 (C O), 1651 (C O),
1
1523 (C N) cm−1; H NMR (CDCl3): δ = 1.07 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.26
(d, J = 15.3 Hz, 1H, CH2 C C), 2.32(d, J = 15.1 Hz, 1H, CH2 C C), 2.64 (br, 2H,
CH2 C O), 3.83 (s, 3H, OCH3), 3.88 (s, 6H, 2OCH3), 6.19 (s, 1H, HPyrimidine), 6.78(d,
J = 7.9 Hz, 1H, Harom.), 6.93 (d, J = 6.8 Hz, 1H, Harom.), 7.01(t, 3H, Harom.), 7.47(d, J =
8.4, 2H, Harom.), 7.78 (s, 1H, H vinyl); 13C NMR (CDCl3): δ = 27.6 (CH3), 29.2 (CH3), 32.7
(CH), 44.9 (CH2), 50.9 (CH2), 53.4 (C-5), 55.5 (OMe), 55.8 (OMe), 55.9 (OMe), 110.9,
111.2, 114.9, 116.6, 119.9, 125.7, 132.2, 132.7, 134.3, 148.8, 149.1, 156.1, 159.7, 161.6,
165.4 (N C O), 196.0 (C O); Anal.calcd for C28H28N2O5S: C, 66.65; H, 5.59; N, 5.55;
S, 6.35. Found: C, 66.51; H, 5.49; N, 5.46; S, 6.22.
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