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mixture was refluxed for an appropriate time (see below) and then the mixture was poured into cold water
(100 mL). The precipitate was filtered and recrystallized from ethyl acetate to give the corresponding
3(4H)-quinazolinone derivatives 3a-d as yellow crystals.
.
3-Methyl-2-({5-oxo-2-phenyl-4-[1-phenylmethylidene]-4,5-dihydro-1H-imidazol-1-yl}amino)-4(3H)-
quinazolinone (3a). Reflux time: 48 hr; yield 71%; m.p. 335-337°C (decomp.); IR (KBr) υmax: 3408 (N-H),
1714 (C=O), 1682 (C=O), 1617 (C=N), 1602 (C=N) cm-1; 1H-NMR (DMSO-d6) δ ppm: 3.37 (s, 3H, CH3),
7.19-8.40 (m, 15H, vinyl, ArH), 10.97 (s, 1H, NH); 13C-NMR (DMSO-d6) δ ppm: 29.1, 116.1, 123.5,
127.2, 128.5, 129.4, 129.6, 130.9, 132.7, 133.0, 135.7, 147.2, 150.4, 151.4, 152.3, 153.0; MS m/z (%):
421 (M+, 19), 249 (24), 105 (100), 91 (54), 77 (62); Anal. Calcd. For C25H19N5O2: C, 71.26; H, 4.51; N,
16.63. Found: C, 71.42; H, 4.44; N, 16.73.
2-({4-[1-(4-Chlorophenyl)methylidene]-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl}amino)-3-methyl-
4(3H)-quinazolinone (3b). Reflux time: 72 hr; yield 43%; m.p. 352-354°C (decomp.); IR (KBr) υmax: 3394
(N-H), 1714 (C=O), 1692 (C=O), 1626 (C=N), 1602 (C=N) cm-1; 1H-NMR (DMSO-d6) δ ppm: 3.40(s, 3H,
CH3), 7.02-8.33 (m, 14H, Vinyl, ArH), 10.98 (s, 1H, NH); 13C-NMR (DMSO-d6) δ ppm: 29.3, 119.3,
123.5, 127.9, 128.1, 129.3, 129.7, 130.9, 131.5, 133.6, 134.8, 35.7, 147.2, 151.4, 151.9, 153.1, 154.7; MS
m/z (%): 457 (M+2, 5), 455 (M+, 14), 277 (36), 249 (22), 105 (100), 91 (88), 77 (62); Anal. Calcd. For
C25H18N5O2Cl: C, 65.86; H, 3.95; N, 15.37. Found: C, 66.02; H, 4.10; N, 15.33.
2-({4-[1-(4-Methoxyphenyl)methylidene]-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl}amino)-3-methyl-
4(3H)-quinazolinone (3c). Reflux time: 24 hr; yield 84%; m.p. 356-358°C (decomp.); IR (KBr) υmax: 3390
1
(N-H), 1700 (C=O), 1692 (C=O), 1632 (C=N), 1606 (C=N) cm-1; H-NMR (DMSO-d6) δ ppm: 3.39 (s,
3H, CH3), 3.85 (s, 3H, OCH3), 7.12-8.38 (m, 14H, vinyl, ArH), 10.91 (s, 1H, NH); 13C-NMR (DMSO-d6)
δ ppm: 28.9, 55.9, 115.6, 121.2, 123.3, 126.3, 128.2, 128.7, 129.5, 130.5, 131.2, 133.1, 134.4,134.7, 147.2,
151.6, 153.3, 154.7, 160.6; MS m/z (%): 451 (M+, 10), 277 (43), 105 (85), 91 (100), 77 (29); Anal. Calcd.
For C26H21N5O3: C, 69.18; H, 4.66; N, 15.52. Found: C, 69.09; H, 4.51; N, 15.43.
2-[(4-Cyclohexyliden-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)amino]-3-methyl-4(3H)-quinazolin-
one (3d). Reflux time: 36 hr; yield 74%; m.p. 340-343°C (decomp.); IR (KBr) υmax: 3400 (N-H), 2950 (C-
1
H), 1714 (C=O), 1686 (C=O), 1636 (C=N), 1594 (C=N) cm-1; H-NMR (DMSO-d6) δ ppm: 3.42 (s, 3H,
CH3), 1.43-2.22 (m, 10H, cyclohexyl), 7.17-8.40 (m, 9H, ArH), 10.76 (s, 1H, NH); 13C-NMR (DMSO-d6)
δ ppm: 26.8, 27.4, 30.4, 31.1, 119.6, 121.2, 123.3, 126.2, 128.0, 128.9, 131.2, 132.2, 134.0, 135.4, 146.3,
150.6, 152.7, 153.1; MS m/z (%): 413 (M+, 16), 277 (18), 105 (100), 91 (95), 77 (69); Anal. Calcd. For
C24H23N5O2: C, 69.73; H, 5.57; N, 16.95. Found: C, 69.79; H, 5.41; N, 16.86.
References
1. (a) Wolfe, J. F.; Rathman, T. L.; Sleevi, M. C.; Campbell, J. A.; Greenwood, T. D. Synthesis and
anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones J. Med. Chem. 1990,