1206
E. Kianmehr, H. Estiri, and A. Bahreman
Vol 46
Compound (6e). Yellow solid; mp 142–144ꢀC. IR (KBr) t/
34), 356 (10), 330 (75), 298 (61), 283 (96), 252 (100), 241
(17), 222 (34), 194 (18), 166 (35), 139 (14), 128 (13), 105
(60), 77 (41).
cmꢁ1: 3004, 2842, 1740, 1732, 1624, 1585, 1504, 1398, 1360,
1
1263, 1225, 1201, 1176, 1097, 895, 831, 797 cmꢁ1. H NMR:
Compound (7b). Yellow solid; mp 154–156ꢀC. IR (KBr) t/
d (ppm) 3.39 (s, 3H), 4.0 (s, 3H), 7.23 (d, J ¼ .5 Hz, 1H),
7.67 (m, 6H), 7.77 (m, 1H), 8.90 (m, 1H), 8.91 (d, J ¼ 7.5
Hz, 1H). 13C NMR: d (ppm) 52.5, 53.0, 110.3, 116.5, 122.9,
124.0, 124.7, 126.2, 127.7, 128.0, 128.9, 129.6, 130.1, 130.9,
132.1, 133.0, 139.0, 164.9, 166.2, 186.4. MS (EI, 70 eV) m/z
(%) 467 (Mþ, 81Br, 100), 465 (Mþ, 79Br, 99), 436 (27), 434
(27), 404 (22), 402 (18), 324 (33), 310 (26), 297 (13), 240
(21), 213 (21), 185 (39), 183 (39), 155 (24).
cmꢁ1: 2975, 1730, 1697, 1634, 1612, 1556, 1494, 1437, 1392,
.
1323, 1237, 1213, 1167, 1095, 874 cmꢁ1 1H NMR: d (ppm)
1.11 (t, J ¼ 7.2 Hz, 3H), 1.41 (t, J ¼ 7.2 Hz, 3H), 3.90 (q,
J ¼ 7.2 Hz, 2H), 4.41 (q, J ¼ 7.2 Hz, 2H), 7.4 (m, 2H), 7.46
(t, J ¼ 7.7 Hz, 2H), 7.62 (d, J ¼ 9.4 Hz, 1H),7.67 (m, 2H),
7.8 (m, 1H), 8.03 (d, J ¼ 7.3 Hz, 2H), 8.30 (d, J ¼ 9.4 Hz,
1H). 13C NMR: d (ppm) 14.1, 14.7, 60.9, 62.0, 106.2, 118.3,
119.4, 125.7, 126.0, 128.3, 128.6, 129.1, 129.3, 129.6, 130.5,
132.9, 134.3, 137.6, 138.1, 163.7, 165.2, 188.1. MS (EI, 70
eV) m/z (%) 415 (Mþ, 100), 387 (5), 370 (30), 343 (19), 324
(14), 312 (16), 298 (59), 270 (35), 241 (35), 220 (26), 194
(12), 164 (15), 128 (113), 105 (50), 77 (50).
Compound (6f). Yellow solid; mp 125–126ꢀC. IR (KBr) t/
cmꢁ1: 2363, 1722, 1628, 1585, 1516, 1473, 1450, 1400, 1354,
1
1263, 1196, 1097, 1068, 1030, 960, 916, 833, 796 cm ꢁ1. H
NMR: d (ppm) 1.10 (t, J ¼ 7.1 Hz, 3H), 1.42 (t, J ¼ 7.1 Hz,
3H), 3.80 (q, J ¼ 7.1 Hz, 2H), 4.49 (q, J ¼ 7.1 Hz, 2H), 7.22
(d, J ¼ 7.5 Hz, 1H), 7.66 (m, 4H), 7.72 (d, J ¼ 8.5 Hz, 2H),
7.77 (m, 1H), 8.89 (d, J ¼ 7.5 Hz, 1H), 8.92 (m, 1H). 13C
NMR: d (ppm) 14.0, 14.4, 62.0, 62.1, 110.7, 116.4, 122.8,
124.0, 124.8, 126.2, 127.6, 127.7, 128.1, 128.8, 129.5, 130.0,
131.1, 132.1, 132.8, 139.0, 164.6, 165.9, 186.4. MS (EI, 70
eV) m/z (%) 495 (Mþ, 81Br, 100), 493 (Mþ, 79Br, 99), 450
(13), 448 (14), 421 (27), 376 (28), 348 (17), 297 (29), 264
(19), 238 (36), 220 (24), 199 (18), 183 (24), 164 (17), 149
(21), 139 (16), 128 (14).
Compound (7c). Yellow solid; mp 169–172ꢀC. IR (KBr) t/
cmꢁ1: 2949, 1724, 1710, 1649, 1597, 1573, 1508, 1448, 1421,
1323, 1259, 1213, 1174, 1091, 889cmꢁ1 1H NMR: d (ppm)
.
3.55 (s, 3H), 3.89 (s, 3H), 3.93 (s, 3H), 6.98 (d, J ¼ 8.8 Hz,
2H), 7.41 (m, 2H), 7.55 (d, J ¼ 9.4 Hz, 1H), 7.68 (m, 1H),
7.75 (m,1H), 7.98 (d, J ¼ 8.7 Hz, 2H), 8.22 (d, J ¼ 9.4 Hz,
1H) ppm. 13C NMR: d (ppm) 52.1, 52.7, 56.0, 105.8, 114.4,
118.3, 119.2, 125.6, 126.0, 126.9, 127.1, 127.8, 129.3, 129.6,
130.9, 132.8, 132.9, 137.0, 164.2, 164.8, 165.6, 187.2. MS (EI,
70 eV) m/z (%) 417 (Mþ, 65), 386 (11), 354 (25), 328 (18),
298 (13), 287 (24), 179 (14), 252 (18), 228 (13), 167 (36), 149
(92), 135 (85), 111 (27),97 (40), 83 (48).
Compound (6g). Yellow solid; mp 174–176ꢀC. IR (KBr) t/
cmꢁ1: 2945, 1727, 1720, 1637, 1603, 1502, 1479, 1358, 1273,
1230, 1201, 1176, 1101, 897, 869, 820 cmꢁ1 1H NMR: d
.
Compound (7d). Yellow solid; mp 166–168ꢀC. IR (KBr) t/
(ppm) 3.35 (s, 3H), 4.01 (s, 3H), 7.22 (d, J ¼ 7.5 Hz, 1H),
7.46 (m, 1H), 7.53 (t, J ¼ 7.3 Hz, 2H), 7.66 (m, 2H), 7.69 (d,
J ¼ 7.3Hz,2H), 7.76 (m, 3H), 7.91 (d, J ¼ 8.2 Hz, 2H), 8.8
(m, 1H), 8.90 ( m, 1H), 8.91 (d, J ¼ 7.5 Hz, 1H). 13C NMR:
d (ppm) 52.4, 53.0, 110.1, 116.3, 123.6, 124.1, 124.8, 126.1,
127.3, 127.4, 127.6, 127.7, 128.7,128.8, 129.4, 129.5, 130.0,
130.1, 132.7, 138.9, 140.2, 145.9, 165.1, 166.4, 187.2. MS (EI,
70 eV) m/z (%) 463(Mþ, 100), 432 (22), 400 (45), 387 (13.4),
374 (7.1), 360 (13), 345 (8), 310 (18), 252 (7), 218 (8), 194
(10), 181 (18), 152 (35).
cmꢁ1: 2980, 1716, 1702, 1643, 1597, 1577, 1508, 1441, 1257,
1217, 1173, 1093, 877 cmꢁ1
.
1H NMR: d (ppm)1.13 (t, J ¼
7.2Hz, 3H), 1.4 (t, J ¼ 7.2 Hz, 3H), 3.99 (q, J ¼ 7.2 Hz, 2H),
4.41 (q, J ¼ 7.2 Hz, 2H), 7.0 (d, J ¼ 8.8 Hz, 2H), 7.44 (m,
2H), 7.58 (d, J ¼ 9.4 Hz, 1H), 7.70 (m, 1H), 7.79 (m, 1H),
8.0 (d, J ¼ 8.7 Hz, 2H), 8.29 (d, J ¼ 9.4 Hz, 2H). 13C NMR:
d (ppm) 14.1, 14.7, 56.0, 60.9, 62.0, 106.0, 114.4, 118.4,
119.2, 125.7, 125.9, 126.8, 127.2, 127.7, 129.3, 129.6, 131.0,
132.9, 137.1, 163.8, 164.8, 165.2, 187.2. MS (EI, 70 eV) m/z
(%) 445 (Mþ, 100), 400 (19), 354 (13), 328 (21), 300 (17),
266 (15), 238 (16), 220 (14), 167 (16), 149 (37), 135 (62), 107
(12), 97 (12),77 (17).
Compound (6h). Yellow solid; mp 149–150ꢀC. IR (KBr) t/
cmꢁ1: 2956, 2854, 1736, 1711, 1624, 1604, 1524, 1501, 1470,
ꢁ1
1371, 1352, 1221, 1097, 1020, 920, 800 cm
.
1H NMR: d
Compound (7e). Yellow solid; mp 194–195ꢀC. IR (KBr) t/
(ppm) 1.01 (t, J ¼ 7.1 Hz, 3H), 1.43 (t, J ¼ 7.1 Hz, 3H), 3.77
(q, J ¼ 7.1 Hz, 2H), 4.49 (q, J ¼ 7.1 Hz, 2H), 7.21 (d, J ¼
7.5 Hz, 1H), 7.46 (m, 1H), 7.53 (m, 2H), 7.67 (m, 4H), 7.74
(d, J ¼ 8.2 Hz, 2H), 7.77 (m, 1H), 7.95 (d, J ¼ 8.2 Hz, 2H),
8.89 (d, J ¼ 7.5 Hz, 1H), 8.91 (m, 1H) ppm. 13C NMR: d
(ppm) 14.0, 14.4, 61.9, 62.0, 110.6, 116.2, 123.4, 124.1, 124.9,
126.1, 127.3, 127.4, 127.6, 127.7, 128.71, 128.73, 129.36,
129.44, 129.9, 130.3, 132.5, 138.9, 140.2, 146.0, 164.7, 166.1,
187.2 ppm. MS (EI, 70 eV) m/z (%) 491 (Mþ, 52), 463 (9),
400 (13), 374 (16), 279 (11), 198 (17), 181 (46), 167 (29), 149
(60), 125 (28), 111 (44), 97 (61), 83 (59), 71 (76).
cmꢁ1: 2852, 1742, 1693, 1651, 1583, 1543, 1477, 1446, 1392,
ꢁ1
1267, 1207, 1102, 1095, 885, 810 cm
.
1H NMR: d (ppm)
3.55 (s, 3H), 3.95 (s, 3H), 7.48 (m, 2H), 7.64 (m, 2H), 7.67 (d,
J ¼ 8.4 Hz, 2H), 7.82 (m, 1H), 7.87 (d, J ¼ 8.4 Hz, 2H), 8.28
(d, J ¼ 9.4 Hz, 1H). 13C NMR: d (ppm) 52.2, 52.8, 106.1,
118.3, 119.3, 125.7, 126.2, 126.3, 128.60, 128.62, 129.5,
129.6, 129.7, 131.7, 132.4, 132.8, 136.9, 137.7, 164.0, 165.5,
187.0. MS (EI, 70 eV) m/z (%) 467 (Mþ, 81Br, 100), 465 (Mþ,
79Br, 99), 434 (21), 406 (18), 347 (8), 324 (18), 310 (47), 252
(22), 239 (19), 193 (14), 183 (20), 167 (21), 149 (42), 97 (21),
83 (23), 71 (34).
Compound (7a). Yellow solid; mp 158–160ꢀC. IR (KBr) t/
cmꢁ1: 2993, 2360, 1730, 1697, 1633, 1612, 1550, 1491, 1450,
Compound (7f). Yellow solid; mp 150–152ꢀC. IR (KBr) t/
cmꢁ1: 2937, 1716, 1695, 1645, 1581, 1544, 1483, 1434, 1400,
1418, 1362, 1323, 1259, 1219, 1171, 1093, 877, cmꢁ1 1H
.
1342, 1300, 1257, 1225, 1093, 889cmꢁ1 1H NMR: d (ppm)
.
NMR: d (ppm) 3.48 (s, 3H), 3.95 (s, 3H), 7.47 (m, 2H), 7.54
(t, J ¼ 7.59 Hz, 2H), 7.68 (m, 3H), 7.83 (m, 1H), 8.01 (d, J ¼
7.6 Hz, 2H), 8.30 (d, J ¼ 9.43 Hz, 1H) ppm. 13C NMR: d
(ppm) 52.1, 52.6, 106.0, 118.4, 119.5, 125.7, 126.1, 126.9,
128.4, 129.1, 129.4, 129.5, 129.6, 130.3, 132.9, 134.3, 137.6,
138.1, 164.1, 165.5, 188.2. MS (EI, 70 eV) m/z (%) 387 (Mþ,
1.15 (t, J ¼ 7.2 Hz, 3H), 1.4 (t, J ¼ 7.2Hz, 3H), 3.97 (q, J ¼
7.2 Hz, 2H), 4.42 (q, J ¼ 7.2 Hz, 2H), 7.49 (m,2H), 7.63 (m,
2H), 7.68 (d, J ¼ 8.5 Hz, 2H), 7.84 (m, 1H), 7.90 (d, J ¼ 8.5
Hz, 2H), 8.32 (d, J ¼ 9.4 Hz, 1H). 13C NMR: d (ppm) 14.1,
14.7, 61.0, 62.1, 106.3, 118.3, 119.3, 125.7, 126.0, 126.2,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet