Synthesis of some new biheterocyclic triazole derivatives and..., H. BEKTAS¸, et al.,
132.82 (2C), 137.37 (C)], 144.35 and 144.86 (N=CH, trans/cis), 145.48 (triazole C-3), 153.67 (triazole C-5),
167.95 (C=O). MS (ESI): m/z (%) 529 (M, 22), 531 (M+2, 100), 551 (78), 357 (18), 189 (24), 144 (30).
2-{3-(4-Methylbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-
N ’-(phenylmethylene)acetohydrazide (5d): Yield 87%, mp 270-271 ◦ C; Anal. Calcd. (%) for: C29 H28 N6
O2 : C, 70.71, H, 5.73, N, 17.06, Found; C, 70.75, H, 5.70, N, 17.10; IR (KBr, ν , cm−1): 3340, 3193 (NH), 1705
(triazole C=O), 1691 (hydrazide C=O), 1615 (C=N); 1 H-NMR (DMSO-d6)δ (ppm): 2.46 (s, 3H, CH3), 2.80
(t, 2H, tryp-CH2), 3.41 (s, 2H, benzyl-CH2), 3.66 (t, 2H, tryp-CH2 ,J =6.4 Hz), 4.49 and 4.89 (s, 2H, CH2 ,
trans and cis conformers, trans/cis ratio 75/25), 6.88 (d, 2H, ar-H), 6.97-7.14 (m, 6H, ar-H), 7.35-7.44 (m, 4H,
ar-H), 7.16-7.74 (m, 2H, ar-H), 8.03 and 8.22 (s,1H, N=CH, trans and cis conformers, trans/cis ratio 73/27),
10.95 (s, 1H, tryp-NH), 11.69 and 11.72 s, 1H, NH, trans/cis ratio 70/30 ); 13 C-NMR (DMSO-d6)δ (ppm):
20.49 (CH3), 23.83 (tryp-CH2), 30.49 (benzyl-CH2), 41.87 (tryp-CH2), 46.13 and 46.24 (NCH2 , trans/cis),
ar-C:[110.07 (C), 111.37 (C), 117.96 (C), 118.37(C), 121.04 (C), 123.25 (C), 126.72 (C), 126.85(2C), 128.23
(2C), 128.67 (2C), 129.02 (2C), 129.88 (C), 131.74 (C), 133.80 (C), 135.87 (C), 143.89 (C)], 145.36 and 145.59
(N=CH, trans/cis), 154.05 (triazole C-3), 163.12 (triazole C-5), 167.99 (C=O); MS (ESI): m/z (%) 493 (M+1,
28), 515 (M+Na, 100), 357 (18), 229 (24), 144 (24).
2-{3-(4-Methylbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-
N ’-(2,6-dichlorophenylmethylene)acetohydrazide (5e): Yield 75%, mp 248-249 ◦ C; IR (KBr, ν , cm−1):
3332 (NH), 1710 (C=O), 1688 (C=O), 1600 (C=N); 1 H-NMR (DMSO-d6)δ (ppm): 2.26 (s, 3H, -CH3), 2.80
(t, 2H, CH2), 3.42 (s, 2H, CH2), 3.66 (bs, 2H, CH2), 4.53 and 4.83 (s, 2H, CH2 , trans and cis conformers,
trans/cis ratio 79/21), 6.9 (d, 2H, ar-H, J =6.0 Hz), 6.97-7.12 (m, 5H, ar-H), 7.35-7.48 (m, 3H, ar-H), 7.58 (d,
2H, ar-H), 8.30 and 8.41 (s, 1H, N=CH, trans and cis conformers, trans/cis ratio 78/22), 10.95 (s, 1H, NH),
11.98 (s, 1H, NH); 13 C-NMR (DMSO-d6)δ (ppm): 20.52 (CH3), 23.78 (CH2), 30.49 (CH2), 41.91 (CH2),
46.04 and 46.52 (NCH2 , trans/cis), ar-C: [110.07 (C), 111.40 (C), 117.99 (C), 118.40(C), 121.08 (C), 123.31
(C), 126.75 (C), 128.30 (2C), 128.93 (2C), 129.25 (2C), 129.37 (2C), 131.07 (C), 131.75 (C), 133.86 (C), 135.94
(C), 139.09 (C)], 145.49 and 145.56 (N=CH, trans/cis), 154.14 (triazole C-3), 163.44 (triazole C-5), 168.29
(C=O); MS (ESI): m/z (%) 561 (M+ , 52), 583 (100), 357 (21), 144 (38).
2-{3-(4-Methylbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-
N ’-(3-fluorophenylmethylene)acetohydrazide (5f): Yield 78%, mp 286-287 ◦ C; IR (KBr, ν , cm−1):
3345, 3193 (NH), 1704 (C=O), 1692 (C=O), 1581(C=N); 1 H-NMR (DMSO-d6) δ (ppm): 2.25 (s, 3H, CH3),
2.80 (t, 2H, CH2), 3.41 (s, 2H, CH2), 3.66 (bs, 2H, CH2), 4.51 and 4.91 (s, 2H, CH2 , trans and cis conformers,
trans/cis ratio 73/27), 6.88 (d, 2H, ar-H, J =8.2 Hz), 7.01-7.07 (m, 5H, ar-H), 7.26-7.66 (m, 6H, ar-H), 8.02
and 8.23 (s, 1H, N=CH, trans and cis conformers, trans/cis ratio 68/32), 10.94 (s, 1H, NH), 11.79 and 11.89
(s, 1H, NH, trans and cis conformers, trans/cis ratio 76/24); 13 C-NMR (DMSO-d6)δ (ppm): 20.49 (CH3),
23.78 (tryp-CH2), 30.46 (CH2), 41.88 (CH2), 46.23 and 46.98 (NCH2 , trans/cis), ar-C:[110.07 (C), 111.37 (C),
112.44 (C), 117.96 (C), 118.37 (C), 121.04 (C), 123.26 (C), 123.51 (C), 126.72 (C), 128.23 (2C), 129.02 (2C),
130.71 (C), 131.74 (C), 135.88 (C), 136.03 (C), 136.32 (C), 136.48 (C), 142.52 (C)], 145.40 and 145.62 (N=CH,
trans/cis), 154.03 (triazole C-3), 163.32 (triazole C-5), 168.21 (C=O); MS (ESI): m/z (%) 511 (M+1, 26), 533
(M+Na, 42), 229 (100), 129 (18).
2-{3-(4-Methylbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-
N ’-(2-hydroxyphenylmethylene)acetohydrazide (5g): Yield 85%, mp 273-274 ◦ C; Anal. Calcd. (%)
171