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Quinazolin-4-Chlorophenyl Compounds

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3-(4-acetylphenyl)-6-bromo-2-(4-chlorophenyl)quinazolin-4(3H)-one (2) Compound 1 ( 0.01 mol) fused with p-aminoacetophenone ( 0.01 mol) at 160 oC in an oil bath for 2 h. Crystallized from ethanol to give redish brown crystals of 2, m.p. 210oC in 80% yield. Analysis for C22H14BrClN2O2, Calcd.: % C, 58.24; H, 3.11; N, 6.17, Found: % C, 58.31; H, 3.17; N, 6.20, IR spectrum (KBr, cm-1) showed characteristic absorption bands at 3380 (C-H aromatic), 1710 (C=O of acetyl), at 1690 (C=O of quinazolinone), 1630 (C=N) and at 1590 (C=C). 1HNMR spectrum (DMSO-d6, ppm) showed signals at 2.6 (3H, s, COCH3) and 7.5-8.1 (m, 11H, Ar-H). 13C NMR (DMSO-d6) d ppm: 198, 165, 160.5, 147.5, 143, 137.5, 136.4, 136.3, 135.7, 129.2, 129, 128.5, 126.5, 124.6, 124, 123, 121.7, 26.5 MS (m/z, R.I.): calcd for C22H14BrClN2O2: 453.99; found: 453. General method for the preparation of 3a-e : …show more content…
(E)-6-bromo-2-(4-chlorophenyl)-3-(4-cinnamoylphenyl)quinazolin-4(3H)-one (3a)
Crystallized from ethanol to give brown crystals, m.p. 170oC in 70% yield. Analysis for C29H18BrClN2O2 ; Calcd %C, 64.28; H, 3.35; N, 5.17; Found: %C, 64.30; H, 3.30; N, 5.19; IR: υmax./cm-1 1685 (C=O quinazolinone), 1660 (C=O of the α,β - unsaturated ketone) and at 1590 (C=N).1H-NMR (DMSO-d6, ppm): 6.8-7.0 (2H, d, d, CH=CH) and 7.2-8.1 (m, 16H, Ar-H ). 13C NMR (DMSO-d6): 189,167, 160,148, 145, 139, 137, 136, 135.2, 132.3, 134, 131, 130, 129.8, 129.5, 129.3, 128, 126.7, 124.9, 124.6, 123. 121.7, 121.3.MS (m/z, R.I.): calcd for: C29H18BrClN2O2 542.02; found: 542

(E)-6-bromo-2-(4-chlorophenyl)-3-(4-(3-(4-chlorophenyl)acryloyl)phenyl)quinazolin-4(3H)-one

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