K. Rad-Moghadam, M. Sharifi-Kiasaraie / Tetrahedron 65 (2009) 8816–8820
8819
J 7.9 Hz), 7.05 (2H, t, J 7.6 Hz), 6.90 (2H, s, two 2-H of indoles), 6.88
(2H, t, J 7.1 Hz), 6.02 (1H, s, ArCH), 2.50 (3H, s, CH3).
(1H, s), 7.57 (2H, d, J 7.5 Hz), 7.29 (2H, d, J 7.0 Hz), 7.10–7.20 (4H, m),
6.97–7.01 (3H, m), 6.85 (1H, s), 6.78 (1H, t), 6.64 (2H, m), 1.93 (3H,
s); dC (125.8 MHz, CDCl3) 193.2, 149.8, 1414.9, 139.2, 137.5, 135.9,
131.9,129.6,128.9,128.7,128.4,128.2,128.0,123.4,121.1,119.8,119.6,
112.0, 110.8, 13.4; m/z (EI, 70 eV) 337 (30, Mþ), 325 (29), 324 (100),
315 (60), 253 (19), 156 (67).
3.7. 3-((1H-Indol-3-yl)(4-nitrophenyl)methyl)-
1H-indole (3d)
Yellow needles (0.34 g, 92%), mp 218–220 ꢀC, lit.12 mp 217–
219 ꢀC; dH (500.1 MHz, DMSO-d6) 10.92 (2H, br s, two NH), 8.15 (2H,
d, J 8.7 Hz, Ar), 7.61 (2H, d, J 8.7 Hz, Ar), 7.37 (2H, d, J 8.1 Hz), 7.29
(2H, d, J 7.9 Hz), 7.05 (2H, t, J 7.4 Hz), 6.90 (2H, s, two 2-H of indoles),
6.88 (2H, t, 7.5 Hz), 6.03 (1H, s, ArCH).
3.15. 3-(5-Bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-
one (6c)
Orange solid (0.37 g, 89%), mp 219–220 ꢀC; [Found C, 68.7; H,
4.1; N, 3.4. C23H16BrNO requires C, 68.67; H, 4.01; N, 3.48%]; nmax
3.8. 3-((1H-Indol-3-yl)(4-chlorophenyl)methyl)-
1H-indole (3e)
(KBr) 3402, 2905, 1540, 1420, 1100, 862, 800 cmꢂ1
; dH
(500.1 MHz, DMSO) 11.9 (1H, s), 7.90 (2H, d, J 7.3 Hz), 7.55 (1H, t,
J 7.3 Hz), 7.52 (1H, s), 7.43–7.48 (3H, m), 7.32–7.36 (4H, m), 7.27
(1H, d, J 8.2 Hz), 7.26 (1H, s), 7.22 (2H, d, J 6.7 Hz); dC (125.8 MHz,
DMSO) 191.3, 151.0, 140.9, 139.9, 136.9, 133.1, 131.6, 130.0, 129.4,
129.0, 128.8, 127.9, 125.5, 123.2, 119.0, 117.5, 115.2, 114.0; m/z (EI,
70 eV) 405 (23, 81Br 81Br, MHþ), 403 (98, 81Br 79Br, MHþ), 401
(96, 79Br 79Br, MHþ), 326 (51), 324 (52), 293 (37), 245 (65), 217
(100), 189 (60%).
Pink solid (0.31 g, 87%), mp 76–77 ꢀC, lit.12 mp 78–80 ꢀC; dH
(500.1 MHz, CDCl3) 7.96 (2H, br s, two NH), 7.40 (4H, d, J 8.5 Hz),
7.32–7.27 (4H, m, Ar), 7.23 (2H, t, J 8.1), 7.05 (2H, t, J 7.8 Hz), 6.69 and
6.68 (2H, 2s, two 2-H of indoles), 5.90 (1H, s, ArCH).
3.9. 3-((1H-Indol-3-yl)(3-nitrophenyl)methyl)-1H-indole (3f)
Yellow solid (0.32 g, 88%), mp 221–223 ꢀC, lit.12 mp 220–222 ꢀC;
dH (500.1 MHz, CDCl3) 8.25 (1H, t, J 1.7 Hz, Ar 20-H), 8.12 (1H, dd,
J 8.1 and 1.3 Hz, Ar 40-H), 8.04 (2H, br s, two NH), 7.73 (1H, d,
J 7.7 Hz, Ar 60-H), 7.48 (1H, t, J 7.9 Hz, Ar 50-H), 7.42 (2H, d, J 8.2 Hz),
7.39 (2H, d, J 7.9 Hz), 7.23 (2H, t, J 7.6 Hz), 7.06 (2H, t, J 7.9 Hz), 6.73
(2H, br s, two 2-H of indoles), 6.04 (1H, s, ArCH).
3.16. 4,4-Bis(1H-indol-3-yl)pentan-2-one (7d)
Colorless solid (0.30 g, 95%), mp 223–225 ꢀC, lit.12 mp 226–228;
[Found C, 79.6; H, 6.3; N, 8.9. C21H20N2O requires C, 79.72; H, 6.37;
N, 8.85%]; nmax (KBr) 3421, 3259, 2920, 1691, 1450, 1340, 1014,
750 cmꢂ1
; dH (500.1 MHz, CDCl3) 8.04 (2H, br s, two NH), 7.40 (2H,
3.10. 2-Methyl-3-((2-methyl-1H-indol-3-yl)
(phenyl)methyl)-1H-indole (3g)
d, J 8.0 Hz), 7.37 (2H, d, J 8.1 Hz), 7.11–7.14 (4H, m, overlap of one
triplet and two singlets), 6.92 (2H, t, J 7.6 Hz), 3.56 (2H, s, CH2), 2.03
(3H, s, Me), 1.58 (3H, s, Me); dC (125.8 MHz, CDCl3) 209.8 (C]O),
137.4 (3 aromatic C), 126.4, 123.4, 122.1 (5CH), 121.7, 121.4, 119.5,
111.6, 53.7 (C-4), 38.3, 32.4, 27.7; m/z (EI, 70 eV) 316 (95, Mþ), 260
(75), 259 (100), 142 (50), 115 (34%).
Pink solid (0.32 g, 92%), mp 244–246 ꢀC, lit.12 mp 244–246; dH
(500.1 MHz, CDCl3) 7.75 (2H, br s, two NH), 7.32–7.23 (7H, m), 7.07
(2H, t, J 7.6 Hz), 7.01 (2H, d, J 8.0 Hz), 6.89 (2H, t, J 7.5 Hz), 6.04 (1H, s,
PhCH), 2.10 (6H, s, 2CH3).
3.17. 4,4-Bis(5-bromo-1H-indol-3-yl)pentan-2-one (7e)
3.11. 2-Methyl-3-((2-methyl-1H-indol-3-yl)-
(4-methylphenyl)methyl)-1H-indole (3h)
White solid (0.44 g, 92%), mp 220–222 ꢀC; [Found C, 53.1; H, 3.9;
N, 5.9. C21H18Br2N2O requires C, 53.19; H, 3.83; N, 5.91%]; nmax (KBr)
Pink solid (0.33 g, 90%), mp 174–176 ꢀC, lit.12 mp 175–177 ꢀC; dH
(500.1 MHz, CDCl3) 7.70 (2H, br s, two NH), 7.26 (2H, d, J 8.0 Hz),
7.20 (2H, d, J 8.0 Hz), 7.09 (2H, d, J 7.3 Hz), 7.07 (2H, t, J 7.9 Hz), 7.04
(2H, d, J 8.0 Hz), 6.90 (2H, t, J 7.5 Hz), 6.00 (1H, s, ArCH), 2.38 (3H, s,
Ar 40-CH3), 2.09 (6H, s, indoles 2-CH3).
3350, 2900, 1680, 1450, 1115, 880, 800 cmꢂ1
; dH (500.1 MHz, DMSO)
11.13 (2H, s, 2 NH), 7.43 (2H, d, J 2 Hz, 40-H), 7.30 (2H, d, J 8.6 Hz,
70-H), 7.17 (2H, d, J 1.1 Hz, 20-H), 7.05 (2H, dd, J 8.6, 1.7 Hz, 60-H), 3.39
(2H, s, CH2), 1.84 (3H, s, Me), 1.59 (3H, s, Me); dC (125.8 MHz, DMSO)
208.4 (C]O), 136.6 (4 aromatic C), 128.2, 124.3, 124.0 (4CH), 122.6,
122.0, 114.4,111.4, 53.5 (C-4), 37.4, 32.6, 27.8; m/z (EI, 70 eV) 476 (15,
81Br 81Br, Mþ), 474 (30, 81Br 79Br, Mþ), 472 (16, 79Br 79Br, Mþ), 419
(80), 417 (100), 415 (73), 197 (34), 183 (42%).
3.12. E-3-(1-(1H-Indol-3-yl)-3-phenylallyl)-1H-indole (3i)
Pale yellow solid (0.32 g, 93%), mp 98–100 ꢀC, lit.12 mp 100–
102 ꢀC; dH (500.1 MHz, DMSO-d6) 10.83 (2H, br s, two NH), 7.50 (2H, d,
7.9 Hz), 7.40 (2H, t, J 7.6 Hz), 7.33 (2H, d, J 8.1 Hz), 7.29–7.24 (3H, m),
7.18 (1H, t, 7.4 Hz), 7.14 and 7.13 (2H, 2s, two2-H of indoles), 7.02 (2H, t,
J7.2 Hz), 6.89(2H, t, 7.5 Hz), 6.55(1H, d,J15.4 Hz), 5.35(1H, d,J7.0 Hz).
3.18. 3,3-Bis(5-bromo-1H-indol-3-yl)-5,5-
dimethylcyclohexanone (7f)
White solid (0.49 g, 96%), mp 214–216 ꢀC; [Found C, 56.1; H, 4.3;
3.13. 4-(2-Methyl-1H-3-indolyl)-3-penten-2-one (6a)
N, 5.3. C24H22Br2N2O requires C, 56.05; H, 4.31; N, 5.45%]; nmax (KBr)
3350, 3250, 1580, 1520, 1490, 1480, 1040, 820, 620 cmꢂ1
; dH
Brown solid (0.21 g, 98%), mp 109–110 ꢀC, lit.28 mp 108–110 ꢀC;
dH (500.1 MHz, CDCl3) 8.68 (1H, br s, NH), 7.62–7.21 (4H, m), 6.28
(1H, s, 3-H), 2.58 (3H, s, CH3), 2.49 (3H, s, CH3), 2.29 (3H, s, CH3).
(500.1 MHz, DMSO) 10.59 (1H, s, NH), 8.79 (1H, s, NH), 7.83 (1H, s),
7.18 (1H, d, J 8.6 Hz), 7.12 (2H, br m), 7.02 (1H, d, J 8.6 Hz), 6.76 (1H,
d, J 1.2 Hz), 6.30 (1H, s), 5.10 (1H, d, J 5.2 Hz, 20-H), 3.24 (1H, dd,
J 14.2 and 6.0 Hz, 2-HB), 2.97 (1H, d, J 14.2 Hz, 2-HA), 2.60 (2H, s,
CH2), 2.16 (1H, d, J 16 Hz, 4-HB), 2.12 (1H, d, J 16 Hz, 4-HA), 1.07 (3H,
s, Me), 1.03 (3H, s, Me); dC (125.8 MHz, DMSO) 194.2, 153.5, 140.7,
135.6, 133.7, 132.4, 129.7, 128.8, 124.7, 124.0, 122.4, 121.8, 119.1, 114.8,
114.1, 114.0, 111.7, 50.7, 45.5, 39.8, 32.6, 32.0, 28.9, 28.5; m/z (EI,
70 eV) 516 (26, 81Br 81Br, Mþ), 514 (51, 81Br 79Br, Mþ), 512 (27, 79Br
79Br, Mþ), 501 (83), 499 (100), 497 (90), 319 (45), 317 (45%).
3.14. 3-(2-Methyl-1H-indol-3-yl)-1,3-diphenyl-
prop-2-en-1-one (6b)
Orange solid (0.31 g, 93%), mp 185–187 ꢀC; [Found C, 85.5; H,
5.7; N, 4.0. C24H19NO requires C, 85.43; H, 5.68; N, 4.15%]; nmax (KBr)
3250, 1620, 1550, 1460, 1240, 770 cmꢂ1
; dH (500.1 MHz, CDCl3) 9.92