V. Jatav et al. / European Journal of Medicinal Chemistry 43 (2008) 1945e1954
1949
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group), 122.1 (C8 of 4(3H )-quinazolinone ring), 126.9 (C10 of
125.7 (C6 of phenyl ring of 1,3,4-thiadiazole ring), 127.1
(C6 of 4(3H )-quinazolinone ring), 124.3 (Cb of phenyl at C-
00
4(3H )-quinazolinone ring), 127.4 (C2 of phenyl ring of 1,3,4-
00
00
thiadiazole ring), 125.7 (C6 of phenyl ring of 1,3,4-thiadia-
zole ring), 127.1 (C6 of 4(3H )-quinazolinone ring), 127.6
(Cb00 of phenyl at C-2 of 4(3H )-quinazolinone ring), 133.8
2 of 4(3H )-quinazolinone ring), 160.9 (C4 of phenyl ring
of 1,3,4-thiadiazole ring), 114.6 (C3 of phenyl ring of
00
1,3,4-thiadiazole ring), 114.6 (C500 of phenyl ring of 1,3,4-thia-
diazole ring), 136.3 (Ca of phenyl ring at C-2 of 4(3H )-quina-
zolinone ring), 133.7 (Ce of phenyl ring at C-2 of 4(3H )-
quinazolinone ring), 128.1 (Cd of phenyl ring at C-2 of
4(3H )-quinazolinone ring), 136 (Cy of styryl group), 147.8
(C9 of 4(3H )-quinazolinone ring).
00
(C4 of phenyl ring of 1,3,4-thiadiazole ring), 123.9 (C3 of
00
phenyl ring of 1,3,4-thiadiazole ring), 130.2 (C5 of phenyl
ring of 1,3,4-thiadiazole ring), 130.2 (Ca of phenyl ring at
C-2 of 4(3H )-quinazolinone ring), 136 (Cy of styryl group),
147.8 (C9 of 4(3H )-quinazolinone ring).
5.1.3.6. Compound 4f. IR (cmꢀ1) 1737 (C]O), 1610 (C]C)
alkene, 1532 (C]N), 1269 (CN), 733 (CS). 1H NMR
(300 MHz, d) 5.60 (d, 1H, olefinic CH, J ¼ 15.6 Hz), 6.99
(d, 2H, olefinic CH), 6.78e8.01 (a set of signals, 13H, aro-
matic protons and olefinic CH). 13C NMR (d) 167 (C-2),
168.9 (C-4), 112 (C-4), 136 (C-12), 134 (C-100), 134 (C-13),
125 (CA), 130 (CB), 112 (Cx of styryl group), 122.1 (C8 of
4(3H )-quinazolinone ring), 126.9 (C10 of 4(3H )-quinazoli-
5.1.3.9. Compound 4i. IR (cmꢀ1) 1701 (C]O), 1637 (C]C)
alkene, 1530 (C]N), 1267 (CN), 774 (CS). 1H NMR
(300 MHz, d) 2.35 (s, 3H, CH3), 5.84 (d, 1H, olefinic CH,
J ¼ 15.1 Hz), 6.12e7.85 (a set of signals, 12H, aromatic pro-
tons and olefinic CH). 13C NMR (d) 165 (C-2), 168 (C-4), 112
(C-11), 136 (C-12), 133.5 (C-100), 131.4 (C-13), 21.4 (CA),
122.1 (C8 of 4(3H )-quinazolinone r0i0ng), 126.9 (C10 of
4(3H )-quinazolinone ring), 127.4 (C2 of phenyl ring of
1,3,4-thiadiazole ring), 125.7 (C600 of phenyl ring of 1,3,4-thia-
diazole ring), 127.1 (C6 of 4(3H )-quinazolinone ring), 124.3
(Cb of phenyl at C-2 of 4(3H )-quinazolinone ring), 140.2
(C400 of phenyl ring of 1,3,4-thiadiazole ring), 129 (C300 of phe-
00
none ring), 127.4 (C2 of phenyl ring of 1,3,4-thiadiazole
00
ring), 125.7 (C6 of phenyl ring of 1,3,4-thiadiazole ring),
127.1 (C6 of 4(3H )-quinazolinone ring), 127.6 (Cb of phenyl
00
at C-2 of 4(3H )-quinazolinone ring), 133.8 (C4 of phenyl
00
00
ring of 1,3,4-thiadiazole ring), 123.9 (C3 of phenyl ring of
nyl ring of 1,3,4-thiadiazole ring), 129 (C5 of phenyl ring of
1,3,4-thiadiazole ring), 130.2 (C200 of phenyl ring of 1,3,4-thia-
diazole ring), 130.2 (Ca of phenyl ring at C-2 of 4(3H )-quina-
zolinone ring), 136 (Cy of styryl group), 147.8 (C9 of 4(3H )-
quinazolinone ring).
1,3,4-thiadiazole ring), 136.3 (Ca of phenyl ring at C-2 of
4(3H )-quinazolinone ring), 133.7 (Ce of phenyl ring at C-2
of 4(3H )-quinazolinone ring), 128.1 (Cd of phenyl ring at C-
2 of 4(3H )-quinazolinone ring), 136 (Cy of styryl group),
147.8 (C9 of 4(3H )-quinazolinone ring).
5.1.3.7. Compound 4g. IR (cmꢀ1) 1700 (C]O), 1620 (C]C)
alkene, 1542 (C]N), 1274 (CN), 740 (CS). 1H NMR
(300 MHz, d) 5.16 (d, 1H, olefinic CH, J ¼ 15.5 Hz), 6.6e
7.92 (a set of signals, 13H, aromatic protons and olefinic
CH). 13C NMR (d) 158.8 (C-2), 168.6 (C-4), 112 (C-11),
136 (C-12), 136.5 (C-100), 134.5 (C-13), 112 (Cx of styryl
group), 122.1 (C8 of 4(3H )-quinazolinone ring), 126.9 (C10
5.1.3.10. Compound 4j. IR (cmꢀ1) 1734 (C]O), 1634
(C]C) alkene, 1542 (C]N), 1293 (CN), 658 (CS). 1H
NMR (300 MHz, d) 5.52 (d, 1H, olefinic CH, J ¼ 15.2 Hz),
6.80e7.48 (a set of signals, 12H, aromatic protons and ole-
finic CH). 13C NMR (d) 167 (C-2), 168.7 (C-4), 112 (C-
11), 135.8 (C-12), 134.6 (C-100), 131.4 (C-13), 122.1 (C8 of
4(3H )-quinazolinone ring), 126.9 (C10 of 4(3H )-quinazoli-
00
of 4(3H )-quinazolinone ring), 127.4 (C2 of phenyl ring of
1,3,4-thiadiazole ring), 125.7 (C600 of phenyl ring of 1,3,4-thia-
diazole ring), 127.1 (C6 of 4(3H )-quinazolinone ring), 124.3
(Cb00 of phenyl at C-2 of 4(3H )-quinazolinone ring), 133.8
none ring), 127.4 (C2 of phenyl ring of 1,3,4-thiadiazole
00
00
ring), 125.7 (C6 of phenyl ring of 1,3,4-thiadiazole ring),
127.1 (C6 of 4(3H )-quinazolinone ring), 124.3 (Cb of phenyl
00
00
(C4 of phenyl ring of 1,3,4-thiadiazole ring), 123.9 (C3 of
at C-2 of 4(3H )-quinazolinone ring), 130.2 (C4 of phenyl
00
00
phenyl ring of 1,3,4-thiadiazole ring), 130.2 (C5 of phenyl
ring of 1,3,4-thiadiazole ring),00 129 (C3 of phenyl ring of
ring of 1,3,4-thiadiazole ring), 136.3 (Ca of phenyl ring at
C-2 of 4(3H )-quinazolinone ring), 133.7 (Ce of phenyl ring
at C-2 of 4(3H )-quinazolinone ring), 128.1 (Cd of phenyl
ring at C-2 of 4(3H )-quinazolinone ring), 136 (Cy of styryl
group), 147.8 (C9 of 4(3H )-quinazolinone ring).
1,3,4-thiadiazole ring), 129 (C5 of phenyl ring of 1,3,4-thia-
diazole ring), 136.3 (Ca of phenyl ring at C-2 of 4(3H )-qui-
nazolinone ring), 133.7 (Ce of phenyl ring at C-2 of 4(3H )-
quinazolinone ring), 128.1 (Cd of phenyl ring at C-2 of
4(3H )-quinazolinone ring), 136 (Cy of styryl group), 147.8
(C9 of 4(3H )-quinazolinone ring).
5.1.3.8. Compound 4h. IR (cmꢀ1) 1739 (C]O), 1642 (C]C)
alkene, 1542 (C]N), 1334 (CN), 759 (CS). 1H NMR
(300 MHz, d) 3.73 (s, 3H, CH3), 5.74 (d, 1H, olefinic CH,
J ¼ 15.4 Hz), 6.83e8.00 (a set of signals, 12H, aromatic pro-
tons and olefinic CH). 13C NMR (d) 167 (C-2), 168.6 (C-4),
112 (C-11), 136 (C-12), 128.8 (C-100), 131.4 (C-13), 55.5
(CA), 56 (CB), 112 (Cx of styryl group), 122.1 (C8 of 4(3H )-
quinazolinone ring), 126.9 (C10 of 4(3H )-quinazolinone
5.1.3.11. Compound 4k. IR (cmꢀ1) 1700 (C]O), 1630 (C]C)
alkene, 1560 (C]N), 1348 (CN), 591 (CS). 1H NMR
(300 MHz, d) 5.12 (d, 1H, olefinic CH, J ¼ 15.2 Hz), 6.41e
7.49 (a set of signals, 12H, aromatic protons and olefinic
CH). 13C NMR (d) 165 (C-2), 168.6 (C-4), 112 (C-11), 136
(C-12), 137.9 (C-100), 131.6 (C-13), 122.1 (C8 of 4(3H )-quina-
zolinone ring), 126.9 (C10 of 4(3H )-quinazolinone ring), 127.4
00
0
0
0
0
ring), 127.4 (C2 of phenyl ring of 1,3,4-thiadiazole ring),
(C2 of phenyl ring of 1,3,4-thiadiazole ring), 125.7 (C6 of