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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, …show more content…
205oC in 75% yield. Analysis for C29H17BrCl2N2O2 ; Calcd %C, 74.99; H, 4.50; N, 6.25; Found: %C, 74.97; H, 4.49; N, 6.24; IR: υmax./cm-1 1690 (C=O quinazolinone), 1660 (C=O of the α,β - unsaturated ketone) and at 1610 (C=N).1H-NMR spectrum (DMSO-d6, ppm): 7.0-7.2 (2H, d, d, CH=CH) and 7.3-8.24(m, 15H, Ar-H ). 13C NMR (DMSO-d6) d ppm: 190,168, 161,148, 146.2, 139.5, 138, 136.6, 135.2, 133.3, 135, 1342, 131, 130, 129.6, 129.3, 128, 126.9, 125.9, 124.8, 123.1. 121.9, 121.5 MS (m/z, R.I.): calcd for: C29H17BrCl2N2O2: 575.98; found: 575. (E)-6-bromo-2-(4-chlorophenyl)-3-(4-(3-(4-nitrophenyl)acryloyl)phenyl)quinazolin-4(3H)-one (3c) Crystallized from glacial acetic acid to give white crystals, m.p. 210oC in 75% yield. Analysis for C29H17BrClN3O4 ; Calcd %C, 77.76; H, 4.66; N, 6.48; Found: %C, 77.72; H, 4.64; N, 6.46; IR: υmax./cm-1 1700 (C=O quinazolinone), 1670 (C=O of the α,β - unsaturated ketone) and at 1600 (C=N).1HNMR (DMSO-d6, ppm) : 6.9-7.1 (2H, d, d, CH=CH) and 7.4-8.5(m, 15H, Ar-H ). 13C NMR (DMSO-d6): 191, 169, 164, 149, 147, 145, 142, 137, 136.5, 134, 132.3, 132, 130,130.5, 129.9, 129, 128.5, 125, 124.5, 123.8, 123, 122.2,122. MS (m/z, R.I.): calcd for: C28H20 N2O3 : 587.01; found: 587 .
(E)-6-bromo-2-(4-chlorophenyl)-3-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)quinazolin-4(3H)-one

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