2542
HETEROCYCLES, Vol. 83, No. 11, 2011
6.55; N, 6.43%.
Diethyl bis[2-(4-methylphenyl)-1H-indol-3-yl]methylmalonate 3b
Compound 3b was obtained as pinkish powder, Mp 199-200 ºC; yield: (10.5 g, 72%); IR (KBr) 3409, 3383,
977, 1731, 1710, 1457, 1271, 1184, 1153, 1033, 847, 737, 519 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 0.71
(6H, t, J = 7.0 Hz, 2OCH2Me), 2.38 (6H, s, 2CH3-Ar), 3.74-3.79 (2H, m, OCH2Me), 3.81-3.84 (2H, m,
OCH2Me), 5.03 (1H, d, J = 12.0 Hz, CH-CH(CO2Et)2), 5.80 (1H, d, J = 12.1 Hz, CH-CH(CO2Et)2), 6.82
(2H, t, J = 7.4 Hz, ArH), 6.96 (2H, t, J = 7.5 Hz, ArH), 7.09 (4H, d, J = 7.8 Hz, ArH), 7.20 (6H, m, ArH),
7.55 (2H, d, J = 8.0 Hz, ArH), 10.88 (2H, s, 2NH); 13C NMR (125.7 MHz, DMSO-d6) δ 14.0, 35.1, 55.3,
61.7, 111.7, 112.6, 119.1, 120.9, 121.4, 128.0, 129.5, 129.9, 131.3, 136.2, 136.5, 137.7, 168.9; MS m/z 584
(M+, 87), 425 (100), 377 (21), 333 (27), 304 (22), 258 (73), 231 (53.9), 207 (34), 133 (40), 115 (53), 88 (38),
60 (16), 43 (62%); Anal. Calcd for C38H36N2O4: C, 78.06; H, 6.21; N, 4.79 %. Found: C, 78.04; H, 6.20; N,
4.82%.
Diethyl bis[2-(4-chlorophenyl)-1H-indol-3-yl]methylmalonate 3c
Compound 3c was obtained as yellow powder, Mp 137-139 ºC; yield: (10.9 g, 70%); IR (KBr) 3410, 3357,
1
3055, 2978, 1735, 1704, 1485, 1372, 1331, 1186, 1093, 1014, 833, 739, 518 cm-1; H NMR (500 MHz,
DMSO-d6) δ = 0.73 (6H, t, J = 7.0 Hz, 2OCH2Me), 3.82-3.85 (2H, m, OCH2Me), 3.89-3.91 (2H, m,
OCH2Me), 5.28 (1H, d, J = 12.2 Hz, CH-CH(CO2Et)2), 5.81 (1H, d, J = 12.2 Hz, CH-CH(CO2Et)2), 6.92
(2H, t, J = 7.6 Hz, ArH), 7.00 (2H, t, J = 7.6 Hz, ArH), 7.22 (2H, d, J = 7.9 Hz, ArH), 7.28 (8H, m, ArH),
7.82 (2H, d, J = 8.0 Hz, ArH), 11.03 (2H, s, 2NH); 13C NMR (125.7 MHz, DMSO-d6) δ 14.1, 34.6, 55.3,
61.7, 112.0, 113.0, 119.5, 121.1, 121.8, 127.4, 129.0, 131.3, 132.6, 133.6, 135.1, 136.8, 168.9; MS m/z 624
(M+-1, 3), 577 (51), 551 (71), 465 (100), 77 (6), 42 (3%); Anal. Calcd for C36H30N2O4Cl2: C, 69.12; H,
4.83; N, 4.48%, Found: C, 69.15; H, 4.85; N, 4.44%.
Diethyl bis[2-(phenyl)-1H-indol-3-yl]methylmalonate 3d
Compound 3d was obtained as pinkish powder, Mp 184-185 ºC; yield: (9.8 g, 71%); IR (KBr) 3396, 3346,
2983, 1742, 1697, 1453, 1288, 1224, 1026, 769, 734, 502 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 0.69 (6H,
t, J = 7.0 Hz, 2OCH2Me), 3.70-3.75 (2H, m, OCH2Me), 3.79-3.81 (2H, m, OCH2Me), 4.91 (1H, d, J = 12.1
Hz, CH-CH(CO2Et)2), 5.75 (1H, d, J = 12.1 Hz, CH-CH(CO2Et)2 ), 6.78 (2H, t, J = 7.2 Hz, ArH), 6.96 (2H,
t, J = 7.9 Hz, ArH), 7.19 (2H, d, J = 8.0 Hz, ArH), 7.31-7.39 (10H, m, ArH), 7.44 (2H, d, J = 8.0 Hz, ArH),
11.5 (2H, s, 2NH); 13C NMR (125.7 MHz, DMSO-d6) δ 14.0, 35.1, 55.3, 61.7, 111.7, 113, 119.2, 121, 121.7,
128.0, 129.5, 129.9, 131.3, 136.5, 137.7, 168.9; MS m/z 556 (M+, 8), 397 (16), 193 (100), 165 (27), 133
(38), 115 (51), 88 (18), 60 (11), 43 (35%); Anal. Calcd for C36H32N2O4: C, 77.68; H, 5.79; N, 5.03 %.
Found: C, 77.60; H, 5.72; N, 5.07%.
Procedure for the synthesis of 3e and 4
In the case of 1-methylindole 2e, following the same procedure as the ones for 3a-d, after 12 h, product 4