3
570
Synthesis
R. A. Irgashev et al.
Paper
5
,11-Dihexyl-6,12-diphenyl-2,8-di(quinoxalin-2-yl)-5,11-dihy-
droindolo[3,2-b]carbazole (11a)
Yield (method A/B): 360/200 mg (86/96%); orange crystals; mp 272–
73 °C.
IR (DRA): 3059, 2956, 2927, 2855, 1952, 1823, 1608, 1572, 1540,
6,12-Bis(4-fluorophenyl)-5,11-dihexyl-2,8-di(quinoxalin-2-yl)-
5,11-dihydroindolo[3,2-b]carbazole (11d)
Yield (method A/B): 270/200 mg (62/92%); yellow crystals; mp 323–
324 °C.
2
IR (DRA): 3063, 2954, 2929, 2856, 1959, 1910, 1676, 1608, 1573,
1526, 1500, 1449, 1415, 1351, 1324, 1296, 1269, 1221, 1206, 1172,
1
1
6
1
465, 1445, 1415, 1387, 1350, 1324, 1295, 1267, 1235, 1206, 1173,
152, 1123, 1094, 1061, 1049, 1022, 963, 908, 862, 808, 759, 725, 700,
85, 597 cm
1149, 1124, 1094, 1044, 1016, 964, 904, 870, 840, 807, 791, 757, 702,
–1
–1
.
674, 644, 615, 591, 554, 539, 526, 517, 477 cm
.
1
H NMR (500 MHz, CDCl ): δ = 8.86 (s, 2 H), 8.41 (dd, J = 8.6, 1.7 Hz, 2
H NMR (500 MHz, CDCl ): δ = 9.05 (s, 2 H), 8.32 (dd, J = 8.7, 1.6 Hz, 2
3
3
H), 8.07 (d, J = 8.7 Hz, 4 H), 7.88–7.73 (m, 12 H), 7.71–7.66 (m, 2 H),
H), 8.10 (dd, J = 4.3, 1.1 Hz, 2 H), 8.08 (dd, J = 4.3, 1.1 Hz, 2 H), 7.80–
7.76 (m, 6 H), 7.72–7.68 (m, 2 H), 7.52–7.48 (m, 4 H), 7.47–7.44 (m, 4
H), 4.00–3.94 (m, 4 H), 1.65–1.58 (m, 4 H), 1.32–1.23 (m, 4 H), 1.21–
1.12 (m, 4 H), 1.09–0.98 (m, 4 H), 0.89 (t, J = 7.3 Hz, 6 H).
7.46 (d, J = 8.6 Hz, 2 H), 7.26 (d, J = 1.5 Hz, 2 H), 4.00–3.95 (m, 4 H),
1.67–1.57 (m, 4 H), 1.30–1.21 (m, 4 H), 1.19–1.12 (m, 4 H), 1.02–0.93
(m, 4 H), 0.87 (t, J = 7.3 Hz, 6 H).
13
13
C NMR (126 MHz, CDCl ): δ = 152.4, 143.8, 143.2, 142.4, 140.8,
C NMR (126 MHz, CDCl ): δ = 163.3 (d, J = 248.9 Hz), 152.2, 143.9,
3
3
C,F
1
1
1
38.4, 132.9, 130.5, 129.9, 129.4, 129.2, 128.9, 128.7, 128.5, 126.4,
25.2, 123.2, 123.1, 121.8, 118.6, 109.3, 44.7, 31.4, 28.9, 26.3, 22.5,
4.0.
143.0, 142.5, 141.0, 134.2 (d, JC,F = 3.5 Hz), 133.2, 132.2 (d, JC,F = 7.8
Hz), 131.9, 130.1, 129.4, 129.0, 128.7, 126.8, 125.1, 123.5, 121.9,
117.8, 116.5 (d, JC,F = 21.2 Hz), 109.1, 44.8, 31.5, 28.9, 26.5, 22.5, 14.0.
Anal. Calcd for C58H52N : C, 83.62; H, 6.29; N, 10.09. Found: C, 83.90;
Anal. Calcd for C58H50F N : C, 80.16; H, 5.80; N, 9.67. Found: C, 80.06;
6
2
6
H, 6.61; N, 10.05.
H, 6.02; N, 9.43.
5
,11-Dihexyl-6,12-bis(4-methoxyphenyl)-2,8-di(quinoxalin-2-yl)-
2,8-Bis(benzo[g]quinoxalin-2-yl)-5,11-dihexyl-6,12-diphenyl-
5,11-dihydroindolo[3,2-b]carbazole (12a)
5,11-dihydroindolo[3,2-b]carbazole (11b)
Yield (method A/B): 160/150 mg (36/67%); orange plates; mp 294–
95 °C.
IR (DRA): 3063, 2956, 2931, 2855, 2045, 1895, 1716, 1608, 1572,
Yield (method A/B): 325/175 mg (78/84%); orange crystals; mp 320–
321 °C.
2
IR (DRA): 3215, 3053, 2953, 2927, 2856, 2663, 2343, 1899, 1811,
1759, 1686, 1609, 1465, 1442, 1411, 1352, 1316, 1280, 1260, 1170,
1
1
7
1
543, 1528, 1502, 1466, 1411, 1350, 1283, 1269, 1242, 1206, 1174,
150, 1124, 1094, 1062, 1028, 1009, 965, 925, 908, 889, 869, 830, 812,
1142, 1112, 1092, 1061, 1025, 974, 951, 913, 874, 838, 812, 784, 741,
91, 760, 718, 702, 670, 643, 623, 611, 593, 559, 544, 483 cm–1
.
701, 680, 644, 607, 593, 581, 563, 507, 488, 470 cm
–1
.
1
H NMR (500 MHz, CDCl ): δ = 9.02 (s, 2 H), 8.33 (dd, J = 8.5, 1.8 Hz, 2
H NMR (500 MHz, CDCl ): δ = 8.91 (s, 2 H), 8.63 (d, J = 5.2 Hz, 4 H),
3
3
H), 8.13–8.05 (m, 4 H), 7.78–7.73 (m, 2 H), 7.72–7.65 (m, 6 H), 7.49–
8.53 (dd, J = 8.6, 1.7 Hz, 2 H), 8.11 (d, J = 9.2 Hz, 4 H), 7.92–7.87 (m, 2
H), 7.85–7.79 (m, 8 H), 7.60–7.53 (m, 4 H), 7.49 (d, J = 8.6 Hz, 2 H),
7.31 (d, J = 1.6 Hz, 2 H), 4.04–3.95 (m, 4 H), 1.70–1.59 (m, 4 H), 1.31–
1.22 (m, 4 H), 1.20–1.13 (m, 4 H), 1.04–0.95 (m, 4 H), 0.89 (t, J = 7.3
Hz, 6 H).
7
1
.42 (m, 4 H), 7.34–7.28 (m, 4 H), 4.06 (s, 6 H), 4.05–4.00 (m, 4 H),
.67–1.59 (m, 4 H), 1.30–1.22 (m, 4 H), 1.20–1.13 (m, 4 H), 1.09–0.99
(m, 4 H), 0.88 (t, J = 7.3 Hz, 6 H).
13
C NMR (126 MHz, CDCl ): δ = 160.1, 152.5, 143.8, 143.3, 142.4, 141,
3
13
1
1
1
33.3, 131.5, 130.3, 129.8, 129.3, 129.0, 128.4, 126.4, 124.9, 123.7,
23.6, 122.2, 118.3, 114.8, 109.1, 55.7, 44.7, 31.5, 29.0, 26.5, 22.6,
4.0.
C NMR (126 MHz, CDCl ): δ = 152.23, 144.72, 143.97, 139.06,
3
138.42, 137.82, 134.20, 133.15, 132.97, 130.56, 129.49, 128.79,
128.56, 128.35, 127.29, 127.17, 126.68, 126.51, 126.24, 125.43,
1
2
23.22, 123.17, 122.05, 118.70, 109.51, 44.73, 31.46, 29.02, 26.40,
2.56, 14.03.
Anal. Calcd for C60H56N O : C, 80.69; H, 6.32; N, 9.41. Found: C, 80.35;
H, 6.41; N, 9.16.
6
2
Anal. Calcd for C66H56N : C, 84.95; H, 6.05; N, 9.01. Found: C, 85.12; H,
6
6.17; N, 9.01.
5
,11-Dihexyl-2,8-di(quinoxalin-2-yl)-6,12-di(thiophen-2-yl)-5,11-
dihydroindolo[3,2-b]carbazole (11c)
2
,8-Bis(benzo[g]quinoxalin-2-yl)-5,11-dihexyl-6,12-bis(4-meth-
Yield (method A/B): 150/130 mg (36/62%); orange crystals; mp 305–
oxyphenyl)-5,11-dihydroindolo[3,2-b]carbazole (12b)
306 °C.
Yield (method A/B): 270/200 mg (54/81%); reddish powder; mp 343–
IR (DRA): 3073, 2926, 2850, 1764, 1680, 1611, 1573, 1543, 1504,
344 °C.
1
1
7
1
445, 1432, 1417, 1357, 1327, 1310, 1288, 1267, 1236, 1162, 1139,
127, 1090, 1041, 995, 967, 950, 936, 918, 884, 873, 849, 839, 813,
IR (DRA): 3057, 3003, 2958, 2928, 2855, 2531, 2029, 1948, 1883,
1828, 1765, 1678, 1611, 1563, 1552, 1530, 1502, 1451, 1405, 1388,
1345, 1326, 1284, 1263, 1246, 1173, 1147, 1111, 1097, 1061, 1043,
–1
75, 761, 723, 702, 677, 611, 589, 574, 538, 505, 491 cm
.
H NMR (500 MHz, CDCl ): δ = 9.07 (s, 2 H), 8.49 (dd, J = 8.6, 1.6 Hz, 2
3
9
6
1
69, 953, 924, 908, 891, 875, 829, 811, 796, 783, 760, 746, 698, 659,
H), 8.12–8.08 (m, 4 H), 7.87 (d, J = 5.2 Hz, 2 H), 7.79–7.74 (m, 2 H),
–1
39, 612, 588, 577, 560, 530, 490, 470 cm
.
7
.72–7.67 (m, 2 H), 7.55–7.50 (m, 4 H), 7.48–7.45 (m, 2 H), 7.38 (s, 2
H), 4.20–4.04 (m, 4 H), 1.79–1.69 (m, 4 H), 1.34–1.20 (m, 8 H), 1.19–
.10 (m, 4 H), 0.90 (t, J = 7.1 Hz, 6 H).
Anal. Calcd for C54H48N S : C, 76.74; H, 5.72; N, 9.94. Found: C, 76.74;
H NMR (500 MHz, CDCl ): δ = 9.11 (s, 2 H), 8.64 (s, 4 H), 8.42 (dd, J =
3
1
8.6, 1.8 Hz, 2 H), 8.17–8.07 (m, 4 H), 7.72 (d, J = 8.5 Hz, 4 H), 7.62–7.52
(
4
(
m, 6 H), 7.47 (d, J = 7.9 Hz, 2 H), 7.36 (d, J = 8.6 Hz, 4 H), 4.12 (s, 6 H),
.08–4.03 (m, 4 H), 1.70–1.62 (m, 4 H), 1.31–1.23 (m, 4 H), 1.22–1.14
m, 4 H), 1.10–1.02 (m, 4 H), 0.89 (t, J = 7.3 Hz, 6 H).
Anal. Calcd for C68H60N O : C, 82.23; H, 6.09; N, 8.46. Found: C, 82.18;
6
2
H, 5.87; N, 9.80.
6
2
H, 6.25; N, 8.33.
©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 3561–3572