S. Dayan and N. O. Kalaycioglu
1511, 1484, 1446, 1390, 1332, 1310, 1291, 1280, 1214, 1168,
1094, 1042, 970, 921, 881, 842, 815, 771, 754, 726, 691, 665.
7.65 (s, 1H, -NH-), 7.98 (d, 2H, J = 8 Hz, -Ha); 7.12–8.35 (m, 8H, H1–4
and -Hx–y), 8.37 (s, 1H, -N CH-).13C NMR (CDCl3, ppm); 55.5 (-OCH3),
114.0 (arom. -CH), 116.9 (arom. -CH), 121.4 (arom. -CH), 124.2
(arom. -CH), 125.3 (arom. -CH), 127.4 (arom. -CH), 129.0 (arom. -CH),
129.3 (arom. -CH), 129.6 (arom. -CH), 130.7 (arom. -CH), 132.9
(arom. -CH), 139.7 (arom. -CH), 140.7 (arom. -CH), 149.5 (arom. -CH),
156.5 (-N CH-). IR (cmꢁ1): 3219, 3070, 3001, 2944, 2894, 2838, 1628,
1593, 1575, 1520, 1495, 1484, 1464, 1454, 1437, 1415, 1392, 1341,
1331, 1304, 1278, 1258, 1214, 1161, 1157, 1105, 1092, 1026, 1010,
986, 969, 950, 916, 886, 869, 855, 838, 800, 764, 752, 738, 722, 710,
688, 680, 648, 623, 612, 587, 571, 553, 538, 505, 490, 467.
Compound 1c
Color light-yellow; yield 85%; m.p. 130–132ꢀC. 1H NMR (CDCl3,
d ppm): 2.41 (s, 3H, -(CH3)p), 2.50 (s, 3H, -(CH3)o), 6.99–7.79
(m, 12H, H1–4, -Ha–c, and -Hx–y), 7.84 (s, 1H, -NH-), 8.45 (s, 1H, -
N CH-). 13C NMR (CDCl3, ppm): 19.6 (- (CH3)p), 21.6 (- (CH3)o),
117.0 (arom. -CH), 121.0 (arom. -CH), 125.4 (arom. -CH), 127.1
(arom. -CH), 127.2 (arom. -CH), 127.4 (arom. -CH), 127.4 (arom. -CH),
127.6 (arom. -CH), 128.5 (arom. -CH), 128.7 (arom. -CH), 129.0
(arom. -CH), 132.0 (arom. -CH), 132.7 (arom. -CH), 138.9 (arom. -CH),
158.5 (-N CH-). IR (cmꢁ1): 3225, 3066, 3002, 2921, 1623, 1606,
1583, 1498, 1482, 1463, 1446, 1405, 1395, 1372, 1322, 1313, 1295,
1274, 1251, 1230, 1213, 1170, 1150, 1113, 1089, 1037, 1000, 938,
912, 871, 847, 825, 801, 753, 729, 686, 672.
General Procedure for the Synthesis of Compounds 6–10
A solution of 1–5 (0.50 mmol) in DMSO (2 ml) was added to a
solution of Pd(OAc)2 (0.25 mmol) in DMSO(2 ml) in a Schlenk
tube. The reaction mixture was stirred and heated at 70ꢀC for
12 h, and then cooled. The volatiles were removed under reduced
pressure. The residue was washed with diethyl ether (20 ml) and
dried under vacuum.
Compound 1d
Color light yellow; yield 92%; m.p. 145–148ꢀC. 1H NMR
(CDCl3, d ppm): 2.35 (s, 3H, -(CH3)p), 2.50 (s, 6H, - (CH3)o,m), 6.96
(s, 2H, -Hy) 7.02–7.76 (m, 9H, -H1–4 and -Ha–c), 7.84 (s, 1H, -NH-),
8.71 (s, 1H, -N CH-). 13C NMR (CDCl3, ppm): 21.3 (- (CH3)p), 21.7
(- (CH3)o), 116.6 (arom. -CH), 119.9 (arom. -CH), 125.1 (arom. -CH),
127.1 (arom. -CH), 127.4 (arom. -CH), 127.7 (arom. -CH), 128.8
(arom. -CH), 129.1 (arom. -CH), 129.4 (arom. -CH), 130.3 (arom. -CH),
132.1 (arom. -CH), 132.8 (arom. -CH), 139.3 (arom. -CH), 141.0
(arom. -CH), 160.1 (-N CH-). IR (cmꢁ1): 3254, 3065, 2970, 2952, 2910,
2848, 1621, 1607, 1586, 1562, 1488, 1461, 1449, 1433, 1404, 1390,
1379, 1329, 1312, 1278, 1210, 1165, 1152, 1090, 1074, 1037, 1027,
998, 979, 9441, 914, 853, 829, 755, 743, 718, 687, 667, 654, 603, 580,
566, 551, 540, 519, 500, 473, 458.
Data for Compounds 6–10
Compound 6
Color brown; yield 73%; m.p. 300–301ꢀC (dec.). 1H NMR (DMSO-d6,
d ppm): 6.55 (s, 4H, -NH2), 6.68–6.74 (m, 2H, -H1,3), 6.90 (t, 2H,
J = 8 Hz, -H2), 7.03 (d, 2H, J = 8 Hz, -H4), 7.41–7.96 (m, 10H, -Hx–z),
13C NMR (DMSO-d6, ppm): 115.2 (arom. -CH), 121.5 (arom. -CH),
127.2 (arom. -CH), 129.2 (arom. -CH), 129.5 (arom. -CH), 130.0
(arom. -CH), 130.2 (arom. -CH), 133.1 (arom. -CH), 135.7 (arom. -CH),
143.5 (arom. -CH). IR (cmꢁ1): 3228, 3217, 2987, 2906, 2838, 2799,
1616, 1575, 1488, 1455, 1445, 1429, 1414, 1399, 1299, 1264, 1242,
1165, 1155, 1121, 1107, 1080, 1039, 1023, 948, 926, 893, 866, 847,
817, 775, 753, 718, 688, 652, 624, 584, 556.
Compound 1e
1
Color yellow; yield 72%; m.p. 225–227ꢀ. H NMR (CDCl3, d ppm):
7.10–7.79 (m, 9H, -H1–4 and -Ha–c), 7.81 (s, 1H, -NH-), 7.97 (d, 2H,
J = 8 Hz, -Hx), 8.35 (d, 2H, J = 8 Hz, -Hy), 8.36 (s, 1H, -N CH-). 13C
NMR (CDCl3, ppm): 116.8 (arom. -CH), 121.4 (arom. -CH), 124.2
(arom. -CH), 125.5 (arom. -CH), 127.1 (arom. -CH), 127.2
(arom. -CH), 127.4 (arom. -CH), 127.7 (arom. -CH), 128.8 (arom. -CH),
128.9 (arom. -CH), 129.0 (arom. -CH), 129.6 (arom. -CH), 132.9
(arom. -CH), 133.2 (arom. -CH), 156.7 (-N CH-). IR (cmꢁ1): 3287, 3103,
3077, 3055, 2841, 1623, 1590, 1507, 1494, 1484, 1462, 1447, 1378,
1338, 1313, 1288, 1277, 1209, 1182, 1154, 1104, 1090, 1076, 1047,
1025, 1014, 1000, 977, 956, 923, 885, 850, 825, 757, 728, 716, 693,
685, 626, 583, 559, 534, 512, 501, 460.
Compound 7
1
Color brown; yield 68%; m.p. >350ꢀC (dec.). H NMR (DMSO-d6,
d ppm): 6.53 (s, 4H, -NH2), 6.78–7.59 (m, 8H, -H1–4), 8,14 (d, 4H,
J = 12 Hz, -Hb), 8,33 (d, 4H, J = 8 Hz, -Ha). 13C NMR (DMSO-d6, ppm):
121.8 (arom. -CH), 122.5 (arom. -CH), 124.6 (arom. -CH), 126.5
(arom. -CH), 127.1 (arom. -CH), 128.4 (arom. -CH), 136.7
(arom. -CH), 146.9 (arom. -CH), 149.3 (arom. -CH), 149.4 (arom. -CH).
IR (cmꢁ1): 3253, 3184, 3099, 3074, 3034, 3867, 2795, 1605,
1581, 1522, 1489, 1452, 1430, 1400, 1349, 1312, 1297, 1280, 1258,
1243, 1196, 1151, 1122, 1109, 1085, 1030, 1015, 966, 950, 931,
846, 824, 790, 752, 744, 733, 702, 686, 648, 631, 622, 599, 561, 536,
493, 461.
Compound 1f
Color light-yellow; yield 88%; m.p. 120–123ꢀC. 1H NMR (CDCl3,
d ppm): 3.92 (s, 3H, -OCH3), 7.73 (s, 1H, -NH-), 7.00–7.80 (m, 13H,
H1–4, -Ha–c and -Hx–y), 8.10 (s, 1H, -N CH-). 13C NMR (CDCl3, ppm):
55.5 (-OCH3); 114.4 (arom. -CH), 117.0 (arom. -CH), 121.5
(arom. -CH), 125.5 (arom. -CH), 127.1 (arom. -CH), 127.3 (arom. -CH),
127.6 (arom. -CH), 128.5 (arom. -CH), 128.7 (arom. -CH), 129.0
(arom. -CH), 131.1 (arom. -CH), 131.9 (arom. -CH), 132.7 (arom. -CH),
139.2 (arom. -CH), 159.2 (-N CH-). IR (cmꢁ1): 3208, 3065, 2997, 2961,
2836, 1619, 1608, 1591, 1572, 1511, 1499, 1485, 1464, 1448, 1424,
1406, 1386, 1314, 1295, 1276, 1246, 1214, 1149, 1111, 1092, 1034,
1000, 974, 943, 914, 883, 831, 803, 756, 733, 688, 666.
Compound 8
1
Color brown; yield 70%; m.p. 315–316ꢀC (dec.). H NMR (DMSO-
d6, d ppm): 1.27 (s, 18H, -C(CH3)3), 6.63 (s, 4H, -NH2), 6.72–6.78
(m, 4, -H1,3), 6.94 (t, 2H, J = 8 Hz, -H2), 7.08 (d, 2H, J = 8 Hz, -H4),
7.50 (d, 4H, J = 8 Hz, -Hb), 7.94 (d, 2H, J = 8 Hz, -Ha). 13C NMR
(DMSO-d6, ppm): 29.1 (-C(CH3)3), 31.3 (-C(CH3)3), 116.1 (arom. -CH),
118.5 (arom. -CH), 122.7 (arom. -CH), 126.0 (arom. -CH), 127.2
(arom. -CH), 128.1 (arom. -CH), 129.0 (arom. -CH), 135.5
(arom. -CH), 143.8 (arom. -CH), 154.6 (arom. -CH). IR (cmꢁ1): 3241,
3188, 3158, 3111, 2969, 2958, 2869, 1611, 1595, 1573, 1516, 1486,
1463, 1452, 1396, 1361, 1301, 1284, 1262, 1238, 1192, 1161, 1138,
1107, 1097, 1080, 1035, 1015, 979, 954, 849, 828, 813, 774, 750,
735, 704, 652, 633, 615, 573, 566, 552, 537.
Compound 4e
Color light-yellow; yield 79%; m.p. 183–185ꢀC. 1H NMR
(CDCl3, d ppm): 3.75 (s, 3H, -OCH3), 6.75 (d, 2H, J = 8 Hz, -Hb),
wileyonlinelibrary.com/journal/aoc
Copyright © 2012 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2013, 27, 52–58