HETEROCYCLES, Vol. 76, No. 2, 2008
1009
Table-1: Physical spectral and micro analytical data of 3-6 8,9
Entry
3
Yield Mp
Spectra
70
20
85
233 IR (KBr):554, 680, 734, 836, 879, 1002, 1158, 1229, 1274, 1380, 1478, 1539, 1591, 1679, 2364, 3450, cm-1; 1H NMR (300 MHz, CDCl3): δ 1.25
(bs, 1H, NH), 7.07-8.22 (m, 8H, Ar-H); 13CNMR(CDCl3): 99.64, 113.26, 117.12, 118.28, 119.40, 128.82, 130.12, 131.12, 133.80, 134.24,
136.61, 151.72, 152.24, 178.33, 179.12; MS: M+(M++1): 309; Anal. Calcd (C17H9ClN2O2): C, 66.14; H, 2.94; N, 9.07 Found: C, 65.85; H, 2.70;
N, 8.94
4
258 IR (KBr): 505, 617, 645, 716, 761, 793, 851, 912, 1016, 1095, 1135, 1241, 1287, 1332, 1383, 1469, 1509, 1598, 1677, 2222, 2366, 3265, 3416
cm-1; H NMR (300 MHz, CDCl3 +DMSO-D6): δ 1.25 (bs, 2H, 2NH), 7.02-8.24 (m, 12H, Ar-H); 13CNMR(CDCl3): 99.08, 118.52, 119.02,
1
119.82, 120.85, 126.92, 131.88, 135.42, 134.82, 137.02, 151.22, 181.76; MS: M+ (M++1): 391; Anal. Calcd (C24H14N4O2):C, 73.84; H, 3.61; N,
14.35 Found: C, 74.02; H, 3.82; N, 14.60
IR (KBr): 491, 531, 602, 670, 719, 757, 858, 984, 1006, 1038, 1071, 1105, 1203, 1252, 1274, 1302, 1350, 1384, 1460, 1507, 1601, 1655, 2363,
5a
150
2926, 3390, 3451 cm-1; H NMR (300 MHz, CDCl3): δ 1.25 (bs, 2H, NH2), 6.99-8.12 (m, 12H, Ar-H); 13CNMR(CDCl3): 68.90, 90.04, 105.04,
1
116.71, 123.28, 123.51, 126.44, 130.17, 131.79, 132.22, 132.58, 132.65, 133.20, 134.53, 140.80, 142.07, 156.02, 180.21, 182.20; MS:
M+(M++1): 391; Anal. Calcd (C24H14N4O2): C, 73.84; H, 3.61; N, 14.35 Found: C, 73.64; H, 3.72; N, 14.52.
IR (KBr): 490, 532, 604, 675, 740, 753, 855, 982, 1008, 1038, 1072, 1106, 1205, 1250, 1276, 1304, 1352, 1388, 1463, 1504, 1607, 1654, 2359,
5b
5c
5d
6a
81
51
83
90
171-
172
2930, 3385, 3460 cm-1; H NMR (300 MHz, CDCl3): δ 1.26 (bs, 2H, NH2), 6.95-8.12 (m, 10H, Ar-H); Anal. Calcd (C24H12Cl2N4O2): C, 62.76;
1
H, 2.63; N, 12.20 Found: C, 62.90; H, 2.80; N, 12.42.
IR (KBr): 495, 533, 605, 674, 742, 754, 858, 985, 1012, 1042, 1073, 1110, 1208, 1254, 1280, 1305, 1354, 1388, 1466, 1512, 1610, 1655, 2363,
2942, 3392, 3462 cm-1; 1H NMR (300 MHz, CDCl3): δ 1.25 (bs, 2H, NH2), 6.98-8.15 (m, 8H, Ar-H); Anal. Calcd (C24H10Cl4N4O2): C, 54.58; H,
1.99; N, 10.69 Found: C, 54.72; H, 2.20; N, 10.82.
198-
199
IR (KBr): 490, 530, 608, 670, 720, 758, 859, 985, 1006, 1036, 1072, 1106, 1204, 1252, 1275, 1304, 1352, 1386, 1462, 1509, 1602, 1656, 2362,
2920, 2932, 3392, 3452 cm-1; 1H NMR (300 MHz, CDCl3): δ 1.25 (bs, 2H, NH2), 2.32 (s, 3H, CH3), 238 (s, 3H, CH3), 6.90-8.15 (m, 10H, Ar-H);
Anal. Calcd (C26H18N4O2): C, 74.63; H, 4.34; N, 13.39 Found: C, 74.84; H, 4.42; N, 13.52.
158-
160
IR (KBr):546, 610,678, 720,816, 869, 965, 1025, 1072, 1124, 1262, 1299, 1337, 1415, 1457, 1520, 1599, 1681, 2942, 3334, 3452 cm-1; 1H NMR
(300 MHz, CDCl3): 1.25 (bs, 2H, NH2) 3.47 (m, 3H, NCH3), 6.49-8.15(m, 8H, Ar-H); 13CNMR(CDCl3): 35.05, 68.92, 105.22, 116.71, 123.52,
126.54, 131.80, 132.58, 133.22, 134.53, 135.88, 140,38, 156.02, 180.40, 182.02; MS: M+(M++1): 304; Anal. Calcd (C18H13N3O2): C, 71.28; H,
4.32; N, 13.85 Found: C, 71.52; H, 4.50; N, 13.98.
90
IR (KBr): 492, 549, 628, 670, 702, 754, 893, 931, 996, 1067, 1121, 1158, 1227, 1252, 1290, 1352, 1460, 1513, 1603, 1672, 2978, 3022, 3224,
3318 cm-1; 1H NMR (300 MHz, CDCl3): δ 1.00 (s, 3H, CH3), 1.03 (s, 3H, CH3), 1.25 (bs, 2H, NH2) 3.55 (m, 1H, isopropyl-H), 6.47-8.11(m, 8H,
Ar-H); MS: M+(M++1): 332; Anal. Calcd (C20H17N3O2): C, 72.49; H, 5.13; N, 12.68 Found: C, 72.32; H, 5.02; N, 12.82.
IR (KBr): 488, 552, 635, 678, 704, 762, 894, 932, 996, 1068, 1125, 1167, 1256, 1292, 1360, 1462, 1514, 1605, 1680, 2854, 2972, 3010, 3264 cm-
1; 1H NMR (300 MHz, CDCl3): 1.25 (bs, 2H, NH2) 1.56 (s, 9H, C(CH3)3), 6.99-8.12(m, 8H, Ar-H); Anal. Calcd (C21H19N3O2): C, 73.03; H, 5.54;
6b
6c
6d
6e
6f
70
68
82
80
55
158
136
oil
N, 12.17 Found: C, 73.28; H, 5.70; N, 12.38
1
IR (Neat): 495, 607, 701, 753, 971, 1027, 1073, 1162, 1289, 1337, 1454, 1499, 1607, 1670, 2857, 2925, 3050, 3064 3347, 3465 cm-1; H NMR
(300 MHz, CDCl3): 1.25 (bs, 2H, NH2) 4.21 (s, 2H, NCH2), 6.60-8.23(m, 13H, Ar-H); Anal. Calcd (C24H17N3O2): C, 75.97; H, 4.52; N, 11.08
Found: C, 76.22; H, 4.78; N, 11.26.
IR (KBr): 473, 498, 583, 663, 724, 756, 797, 858, 905, 971, 1019, 1041, 1084, 1157, 1202, 1263, 1313, 1385, 1474, 1603, 1675, 2932, 2983,
3072, 3372, 3471 cm-1; 1H NMR (300 MHz, CDCl3): 1.25 (bs, 2H, NH2) 6.72-8.05(m, 13H, Ar-H); Anal. Calcd (C23H15N3O2): C, 75.60; H, 4.14;
N, 11.50 Found: C, 75.82; H, 4.30; N, 11.72.
60-
62
IR (KBr):487, 675, 769, 972, 1029, 1081, 1219, 1370, 1461, 1508, 1617, 1657, 2854, 2923, 3370, 3427 cm-1; 1H NMR (300 MHz, CDCl3): 1.25
(bs, 2H, NH2), 2.64 (t, 2H,CH2), 3.31 (t, 2H, CH2), 3.79 (s, 3H, OCH3), 3.80 (s, 3H, OCH3) 6.46-8.09(m, 11H, Ar-H); Anal. Calcd (C27H23N3O4):
C, 71.51; H, 5.11; N, 9.27 Found: C, 71.72; H, 5.32; N, 9.48.
178