6,12-Bis(2-methylphenyl)-5,11-dihydroindolo[3,2-b]carbazole (2c)
6,12-Bis(3,5-di-tert-butylphenyl)-5,11-dihydroindolo[3,2-
b]carbazole (2h)
This compound was prepared starting from indole and 2-
methylbenzaldehyde to give compound 2c (50%) as a slightly
brown solid. Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si):
2.07 (3H, s, CH3), 2.10 (3H, s, CH3), 6.77–6.84 (4H, m, 4 ¥ CH),
7.21–7.25 (2H, m, 2 ¥ CH), 7.42–7.45 (2H, m, 2 ¥ CH), 7.50–7.54
(4H, m, 4 ¥ CH), 7.56–7.59 (4H, m, 4 ¥ CH), 10.47 (1H, s, 1 ¥
NH), 10.48 (1H, s, 1 ¥ NH); dC (75MHz, DMSO-d6, Me4Si): 19.5
(CH3), 19.7 (CH3), 111.4 (CH), 116.3, 118.0 (CH), 120.7, 121.1
(CH), 123.3, 125.4, 127.0 (CH), 128.6 (CH), 130.7 (CH), 130.8
(CH), 130.9 (CH), 133.9, 137.1, 137.5, 137.6, 142.3; HRMS (EI)
calcd for C32H24N2 [M]+, 436.19395; found, 436.19329.
This compound was prepared starting from indole and 3,5-di-tert-
butylbenzaldehyde to give compound 2h (60%) as a yellow solid.
Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si): 1.43 (36H, s,
12 ¥ CH3), 6.92 (2H, t, 2 ¥ CH), 7.28–7.41 (6H, m, 6 ¥ CH), 7.64
(6H, s, 6 ¥ CH), 8.02 (2H, s, 2 ¥ NH); dC (75MHz, DMSO-d6,
Me4Si): 31.6, 35.2, 110.1, 118.1, 118.2, 120.4, 121.7, 122.5, 123.4,
124.3, 125.5, 134.1, 136.0, 140.9, 151.8; MS (ESI) m/z 633 [M +
H]+.
6,12-Bis(4-hydroxy-3,5-di-tert-butylphenyl)-5,11-
dihydroindolo[3,2-b]carbazole (2i)
6,12-Bis(4-methoxyphenyl)-5,11-dihydroindolo[3,2-b]carbazole
This compound was prepared starting from indole and 4-hydroxy-
3,5-di-tert-butylbenzaldehyde to give compound 2i (36%) as a
yellow solid. Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si):
1.53 (36H, s, 12 ¥ CH3), 5.45 (2H, s, 2 ¥ OH), 6.95 (2H, t, 2 ¥ CH),
7.29–7.41 (4H, m, 4 ¥ CH), 7.50 (2H, d, 2 ¥ CH), 7.59 (4H, s, 4 ¥
CH), 8.05 (2H, s, 2 ¥ NH); dC (75MHz, DMSO-d6, Me4Si): 30.5,
34.7, 110.2, 117.8, 118.1, 120.6, 122.3, 123.6, 125.3, 126.7, 127.7,
134.3, 136.8, 140.9, 153.7; MS (ESI) m/z 665 [M + H]+.
(2d)
This compound was prepared starting from indole and 4-
methoxybenzaldehyde to give compound 2d (50%) as a yellow
solid. Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si): 3.94 (6H, s,
CH3), 6.83 (2H, t, 2 ¥ CH), 7.15 (2H, d, J = 7.9 Hz, 2 ¥ CH), 7.22–
7.28 (6H, m, 6 ¥ CH), 7.43 (2H, d, J = 7.9 Hz, 2 ¥ CH), 7.60 (4H,
d, J = 7.7 Hz, 4 ¥ CH), 10.47 (2H, s, 2 ¥ NH); HRMS (EI) calcd
for C32H24N2O2 [M]+, 468.18378; found, 468.18480.
6,12-Bis(4-nitrophenyl)-5,11-dihydroindolo[3,2-b]carbazole (2j)
6,12-Bis(4-hydroxyphenyl)-5,11-dihydroindolo[3,2-b]carbazole (2e)
This compound was prepared starting from indole and 4-
nitrobenzaldehyde to give compound 2j (56%) as a red solid. Mp:
>300 ◦C; dH (300 MHz, DMSO-d6, Me4Si): 6.89 (2H, t, 2 ¥ CH),
7.14 (2H, d, 2 ¥ CH), 7.31 (2H, t, 2 ¥ CH), 7.44 (2H, d, 2 ¥ CH),
8.03 (4H, d, 4 ¥ Ph-H), 8.58 (4H, d, 4 ¥ Ph-H), 10.82 (2H, s, 2 ¥
NH); dC (75MHz, DMSO-d6, Me4Si): 110.1 (CH), 114.5, 116.8
(CH), 118.3, 120.0 (CH), 120.3, 123.3 (CH), 124.6, 130.6 (CH),
132.2, 140.6, 143.0, 146.2; HRMS (EI) calcd for C30H18N4O4 [M]+,
498.13281; found, 498.13483.
This compound was prepared starting from indole and 4-
hydroxybenzaldehyde, and without needing the second oxidation
step we got compound 2e directly (0.97 g, 52%) as a slightly yellow
solid. Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si): 6.83 (2H,
t, 2 ¥ CH), 7.10 (4H, d, 4 ¥ CH), 7.19–7.26 (4H, m, 4 ¥ CH),
7.42–7.49 (6H, m, 6 ¥ CH), 9.72 (2H, br, 2 ¥ OH), 10.43 (2H, s, 2 ¥
NH); dC (75MHz, DMSO-d6, Me4Si): 109.8 (CH), 114.9 (CH),
115.4, 116.0 (CH), 118.9, 120.2 (CH), 121.3, 123.7, 126.2, 129.9
(CH), 132.7, 140.4, 156.0; HRMS (EI) calcd for C30H20N2O2 [M]+,
440.15248; found, 440.15234.
6,12-Bis(4-cyanophenyl)-5,11-dihydroindolo[3,2-b]carbazole (2k)
6,12-Bis(4-bromophenyl)-5,11-dihydroindolo[3,2-b]carbazole (2f)
This compound was prepared starting from indole and 4-
cyanobenzaldehyde to give compound 2k (53%) as a yellow solid.
Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si): 6.89 (2H, t, 2 ¥
CH), 7.07 (2H, d, 2 ¥ CH), 7.30 (2H, t, 2 ¥ CH), 7.44 (2H, d,
2 ¥ CH), 7.92 (4H, d, 4 ¥ Ph-H), 8.20 (4H, d, 4 ¥ Ph-H), 10.75
(2H, s, 2 ¥ NH); dC (75MHz, DMSO-d6, Me4Si): 109.7, 110.0
(CH), 114.7, 116.7 (CH), 117.9, 118.3, 119.9 (CH), 120.4, 124.5
(CH), 130.2 (CH), 132.1 (CH), 140.6, 140.9; HRMS (EI) calcd for
C32H18N4 [M]+, 458.15315; found, 458.15326.
This compound was prepared starting from indole and 4-
bromobenzaldehyde. The crude product was purified with silica
gel chromatography (EtOAc:heptane 1:4) to give compound 2f
(43%) as a yellow solid. Mp: >300 ◦C; dH (300 MHz, DMSO-
d6, Me4Si): 6.99–7.01 (2H, m, 2 ¥ CH), 7.36–7.38 (6H, m, 6 ¥
CH), 7.65 (4H, d, 4 ¥ CH), 7.82–7.88 (6H, m, 4 ¥ CH, 2 ¥ NH);
dC (75MHz, DMSO-d6, Me4Si): 110.4 (CH), 116.1, 118.8 (CH),
120.3, 122.1(CH), 122.5, 122.9(CH), 126.0, 131.8, 132.8 (CH),
133.9 (CH), 135.8, 140.9; MS (CI): m/z 567 (100%) [M + H]+.
X-Ray crystallography of compound 1a
6,12-Bis(2-thienyl)-5,11-dihydroindolo[3,2-b]carbazole (2g)
Crystals of the 6,12-diphenyl-5,6,11,12-tetrahydroindolo[3,2-
b]carbazole 1a were crystallized from a mixture of DMSO and
THF. A translucent plate like crystal with approximate dimensions
of 0.4 ¥ 0.3 ¥ 0.2 mm was selected for data collection using
This compound was prepared starting from indole and thiophene-
2-carboxaldehyde. The crude product was purified with silica gel
chromatography (EtOAc:heptane 1:4) to give compound 2g (47%)
as a yellow solid. Mp: >300 ◦C; dH (300 MHz, DMSO-d6, Me4Si):
6.91 (2H, t, 2 ¥ CH), 7.15 (2H, d, 2 ¥ CH), 7.31 (2H, t, 2 ¥ CH),
7.43–7.50 (6H, m, 6 ¥ CH), 7.95 (2H, d, 2 ¥ CH), 10.78 (2H, s,
2 ¥ NH). dC (75MHz, DMSO-d6, Me4Si): 109.6, 111.1 (CH),
117.7 (CH), 121.1, 121.2 (CH), 121.7, 125.5 (CH), 127.5 (CH),
128.1 (CH), 128.2 (CH), 134.6, 136.7, 141.4; HRMS (EI) calcd for
C26H16N2S2 [M]+, 420.07549; found, 420.07471.
˚
Cu–Ka radiation (l = 1.54178 A) and phi and omega scans. Data
were collected at a temperature of 100 K on a SMART 6000 CCD
detector. The crystals belong to the triclinic space group P-1 with
˚
˚
the following cell parameters: a = 8.6191(3)A, b = 9.4722(4)A,
◦
◦
◦
˚
c = 10.8125(5)A, a= 87.925(2) , b = 80.702(2) , g = 70.015(2) ;
3
˚
cell volume is 818.52(6)A with one molecule in the unit cell.
Data reduction was carried out by the program SAINT11 for a
384 | Org. Biomol. Chem., 2009, 7, 380–385
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The Royal Society of Chemistry 2009
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