Tetrahydrobenzo[b]pyrans
2367
1
838, 775, 706 cm21. H NMR (CDCl3, 400 MHz) d: 0.94 (s, 3H, CH3), 1.03
(s, 3H, CH3), 2.10 (d, J ¼ 16.0 Hz, 1H, C8-H), 2.24 (d, J ¼ 16.0 Hz, 1H,
C8-H), 2.45–2.57 (m, 2H, C6-H), 4.19 (s, 1H, C4-H), 7.02 (s, 2H, NH2),
7.07–7.19 (m, 4H, ArH). Anal. calcd. for C18H17FN2O2: C, 69.22; H, 5.49;
N, 8.97. Found: C, 69.17; H, 5.34; N, 9.10%.
Compound 3d: mp 220–2228C. IR (KBr) n: 3426, 3331, 2957, 2192, 1676,
1640, 1601, 1510, 1459, 1404, 1369, 1318, 1242, 1205, 1157, 1136, 1033,
1
971, 909, 842, 765 cm21. H NMR (CDCl3, 400 MHz) d: 0.95 (s, 3H, CH3),
1.04 (s, 3H, CH3), 2.09 (d, J ¼ 16.0 Hz, 1H, C8-H), 2.24 (d, J ¼ 16.0 Hz,
1H, C8-H), 2.25 (s, 3H, CH3), 2.45–2.56 (m, 2H, C6-H), 4.12 (s, 1H, C4-
H), 6.96 (s, 2H, NH2), 7.02 (d, J ¼ 8.0 Hz, 2H, ArH), 7.08 (d, J ¼ 8.0 Hz,
2H, ArH); Anal. calcd. for C19H20N2O2: C, 74.00; H, 6.54; N 9.08. Found
C, 74.30; H, 6.77; N, 9.31%.
Compound 3e: mp 196–1988C. IR (KBr) n: 3377, 3186, 2964, 2198, 1681,
1655, 1596, 1509, 1456, 1406, 1369, 1249, 1209, 1171, 1157, 1137, 1037,
.
1034, 968, 843, 768 cm21 1H NMR (CDCl3, 400 MHz) d: 0.95 (s, 3H,
CH3), 1.03 (s, 3H, CH3), 2.09 (d, J ¼ 16.0 Hz, 1H, C8-H), 2.24
(d, J ¼ 16.0 Hz, 1H, C8-H), 2.46–2.56 (m, 2H, C6-H), 3.71 (s, 3H, OCH3),
4.12 (s, 1H, C4-H), 6.84 (d, J ¼ 8.0 Hz, 2H, ArH), 6.95 (s, 2H, NH2), 7.05
(d, J ¼ 8.0 Hz, 2H, ArH). Anal. calcd. for C19H20N2O3: C, 74.35; H, 6.21;
N, 8.64. Found: C, 74.25; H, 6.77; N, 8.31%.
Compound 3j: mp: 151–1538C. IR (KBr) n: 3403, 3290, 3027, 2956, 1693,
1655, 1606, 1524, 1475, 1453, 1371, 1288, 1202, 1165, 1081, 1039, 835,
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796, 725, 697 cm21. H NMR (DMSO-d6) d: 0.89 (3H, s, CH3), 1.04 (3H,
s, CH3), 1.09 (3H, t, J ¼ 7.2 Hz CH3), 2.06 (1H, d, J ¼ 16.0 Hz, C8-H),
2.26 (1H, d, J ¼ 16.0 Hz, C8-H), 2.46 (1H, d, J ¼ 17.6 Hz, C6-H), 2.55 (1H,
d, J ¼ 17.6 Hz, C6-H), 3.94 (2H, q, J ¼ 7.2 Hz, CH2O), 4.50 (1H, s, C4-H),
7.02–7.22 (5H, m, ArH), 7.54 (2H, s NH2). Anal. calcd. for C20H23NO4: C,
70.36; H, 6.79; N, 4.10. Found: C, 70.53; H, 6.63; N, 3.97%.
Compound 3k: mp: 153–1548C. IR (KBr) n: 3480, 3327, 2976, 1681, 1665,
1
1524, 1485, 1371, 1302, 1298, 1202, 1165, 1081, 1039, 915, 835 cm21. H
NMR (DMSO-d6) d: 0.89 (3H, s, CH3), 1.04 (3H, s, CH3), 1.09 (3H, t,
J ¼ 7.2 Hz CH3), 2.06 (1H, d, J ¼ 16.0 Hz, C8-H), 2.26 (1H,
d, J ¼ 16.0 Hz, C8-H), 2.46 (1H, d, J ¼ 17.6 Hz, C6-H), 2.55 (1H, d,
J ¼ 17.6 Hz, C6-H), 3.94 (2H, q, J ¼ 7.2 Hz, CH2O), 4.50 (1H, s, C4-H),
7.12–7.22 (5H, m, ArH), 7.56 (2H, s NH2). Anal. calcd. for C20H22ClNO4:
C, 63.91; H, 5.90; N, 3.73. Found: C, 64.08; H, 5.71; N, 3.58%.
Compound 3n: mp: 165–1668C. IR (KBr) n: 3408, 3289, 2976, 1692, 1665,
1
1625, 1520, 1485, 1370, 1298, 1202, 1081, 1039, 835, 789 cm21. H NMR
(DMSO-d6) d: 0.89 (3H, s, CH3), 1.04 (3H, s, CH3), 1.09 (3H, t, J ¼ 7.2 Hz