SYNTHESIS OF 2-ARYLQUINAZOLIN-4(3H)-ONE DERIVATIVES
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J ¼ 7.6 Hz, 1H, ArH), 6.77 (d, J ¼ 8.0 Hz, 1H, ArH), 7.03 (s, 1H, NH), 7.25–7.29 (m,
1H, ArH), 7.40–7.43 (m, 2H, ArH), 7.49–7.52 (m, 1H, ArH), 7.65–7.68 (m, 2H,
ArH), 8.23 (s, 1H, NH). IR (KBr): 3362, 3196, 3066, 3019, 2920, 1647, 1614,
1503, 1484, 1466, 1393, 1351, 1329, 1301, 1252, 1188, 1154, 1123, 1054, 1032,
823, 793, 747, 716 cmꢀ1. HRMS (ESI, m=z): calcd. for C14H12ClN2O (M þ Hþ)
259.0638; found 259.0632.
2,3-Dihydro-2-(2,3-dichlorophenyl)quinazolin-4(1H)-one 5c. Mp > 300 ꢁC.
1H NMR (DMSO-d6, 400 MHz): dH 6.18 (s, 1H, CH), 6.71–6.77 (m, 2H, ArH), 7.10
(s, 1H, NH), 7.25–7.30 (m, 1H, ArH), 7.43 (t, J ¼ 8.0 Hz, 1H, ArH), 7.60–7.69 (m,
3H, ArH), 8.29 (s, 1H, NH). IR (KBr): 3355, 3243, 3079, 2964, 1638, 1503, 1450,
1412, 1385, 1344, 1323, 1295, 1252, 1121, 1106, 1049, 850, 821, 773, 747, 735,
710 cmꢀ1. HRMS (ESI, m=z): calcd. for C14H10Cl2N2NaO (M þ Naþ) 315.0068;
found 315.0064.
2,3-Dihydro-2-(2,4-dichlorophenyl)quinazolin-4(1H)-one 5d. Mp > 300 ꢁC.
1H NMR (CDCl3, 400 MHz): dH 4.74 (s, 1H, NH), 6.28 (s, 1H, CH), 6.66 (d,
J ¼ 8.0 Hz, 1H, ArH), 6.72 (s, 1H, NH), 6.84–6.88 (m, 1H, ArH), 7.27–7.33 (m,
2H, ArH), 7.41 (d, J ¼ 2.0 Hz, 1H, ArH), 7.65 (d, J ¼ 8.4 Hz, 1H, ArH), 7.85 (d,
J ¼ 8.0 Hz, 1H, ArH). IR (KBr): 3339, 3187, 3063, 2906, 1670, 1611, 1592,
1565, 1485, 1451, 1376, 1345, 1298, 1237, 1150, 1102, 1052, 1009, 861, 824, 776,
757 cmꢀ1. HRMS (ESI, m=z): calcd. for C14H10Cl2N2NaO (M þ Naþ) 315.0068;
found 315.0066.
2,3-Dihydro-2-(2-nitrophenyl)quinazolin-4(1H)-one 5e. Mp 206–208 ꢁC
(lit.[18] 191–194 ꢁC). 1H NMR (DMSO-d6, 400 MHz): dH 6.35 (s, 1H, CH),
6.71–7.75 (m, 1H, ArH), 6.78 (d, J ¼ 8.0 Hz, 1H, ArH), 7.01 (s, 1H, NH),
7.25–7.29 (m, 1H, ArH), 7.61–7.68 (m, 2H, ArH), 7.78–7.82 (m, 1H, ArH),
7.86–7.88 (m, 1H, ArH), 8.07 (dd, J ¼ 8.4 Hz, J0 ¼ 1.2 Hz, 1H, ArH), 8.22 (s, 1H,
NH). IR (KBr): 3410, 3185, 3071, 2925, 1659, 1610, 1579, 1538, 1506, 1453, 1433,
1392, 1351, 1333, 1298, 1258, 1175, 1130, 890, 861, 826, 755, 741 cmꢀ1. HRMS
(ESI, m=z): calcd. for C14H12N3O3 (M þ Hþ) 270.0879; found 270.0879.
2,3-Dihydro-2-(2-bromophenyl)quinazolin-4(1H)-one 5f. Mp 193–194 ꢁC.
1H NMR (DMSO-d6, 400 MHz): dH 6.11 (s, 1H, CH), 6.71–7.75 (m, 1H, ArH),
6.78 (d, J ¼ 8.4 Hz, 1H, ArH), 7.01 (s, 1H, NH), 7.26–7.29 (m, 1H, ArH),
7.32–7.36 (m, 1H, ArH), 7.44–7.48 (m, 1H, ArH), 7.66–7.70 (m, 3H, ArH), 8.22
(s, 1H, NH). IR (KBr): 3366, 3190, 3063, 2927, 1656, 1613, 1503, 1485, 1450,
1394, 1351, 1329, 1254, 1188, 1156, 1125, 1026, 821, 792, 748, 713 cmꢀ1. HRMS
(ESI, m=z): calcd. for C14H12BrN2O (M þ Hþ) 303.0133; found 303.0136.
2,3-Dihydro-2-(2-methoxyphenyl)quinazolin-4(1H)-one 5g. Mp 174–175 ꢁC
1
(lit.[19] 163–165 ꢁC). H NMR (DMSO-d6, 400 MHz): dH 3.84 (s, 3H, CH3O), 6.03
(s, 1H, CH), 6.67 (t, J ¼ 7.6 Hz, 1H, ArH), 6.77 (d, J ¼ 8.4 Hz, 1H, ArH), 6.80 (s,
1H, NH), 6.95 (t, J ¼ 7.6 Hz, 1H, ArH), 7.05 (d, J ¼ 8.4 Hz, 1H, NH), 7.21–7.25
(m, 1H, ArH), 7.31–7.35 (m, 1H, ArH), 7.39–7.41 (m, 1H, ArH), 7.63 (d, J ¼ 7.6 Hz,
Hz, 1H, ArH), 8.02 (s, 1H, NH). IR (KBr): 3390, 3317, 3191, 3051, 2933, 1663, 1610,
1504, 1488, 1465, 1388, 1330, 1280, 1242, 1187, 1165, 1151, 1111, 1027, 857, 827, 753,