1292
KIRAN et al.
1
N=CH), 12.03 d.s (11.97*, 1H, NH). 13C NMR spec-
trum, δ, ppm: 49.6, 56.2, 67.5, 109.5, 114.1, 122.4,
122.5, 124.1, 125.5, 128.1, 128.3, 129.3, 129.4, 129.6,
131.2, 146.7, 146.8, 149.3, 149.7, 149.8, 149.9, 161.8.
Found, %: С 61.68; Н 4.53; N 17.30. C25H22N6O5.
Calculated, %: С 61.72; Н 4.56; N 17.28. M 487.22
[M + H]+.
(NH), 1677 (C=O), 1270 (Ar–O). H NMR spectrum,
δ, ppm: 3.67 s (6H, 2OCH3), 3.80 s (3H, OCH3), 3.81 s
(3H, OCH3), 4.48 br.s (2H, NCH2), 4.80 br.s (2H,
OCH2), 6.30 s (2H, Ar-H), 7.07 d (1H, Ar-H, J =
8.0 Hz), 7.20 d (1H, Ar-H, J = 8.0 Hz), 7.35 s (1H, Ar-
H), 7.61 d (2H, Ar-H, J = 8.2 Hz), 7.93 d (2H, Ar-H,
J = 8.2 Hz), 8.04 s (1H, triazole-H), 8.38 s (1H,
N=CH), 11.86 s (1H, NH). 13C NMR spectrum, δ,
ppm: 48.8, 55.3, 55.6, 67.2, 90.9, 101.2, 108.9, 113.4,
121.7, 121.8, 125.1, 125.2, 127.8, 128.5, 129.5, 132.1,
136.4, 148.1, 149.2, 149.3, 158.8, 161.1, 161.9. Found,
%: С 59.41; Н 4.95; N 12.39. С28Н28ClN5О6. Cal-
culated, %: С 59.42; Н 4.99; N 12.37. M 566 [M + H]+.
(E)-4-Bromo-N'-{3-methoxy-4-[2-{4-(2,4,6-trime-
thoxyphenyl)-1H-1,2,3-triazol-1-yl}ethoxy]benzyl-
idene} benzohydrazide (10a). Pale brown solid, yield
86%, mp 99–100°C. IR spectrum, ν, cm–1: 3454 (NH),
1677 (C=O), 1270 (Ar–O). 1H NMR spectrum, δ, ppm:
3.67 s (6H, 2OCH3), 3.80 s (3H, OCH3), 3.82 s (3H,
OCH3), 4.49 br.s (2H, NCH2), 4.80 br.s (2H, OCH2),
6.30 s (2H, Ar-H), 7.07 d (1H, Ar-H, J = 7.5 Hz), 7.21
d (1H, Ar-H, J = 7.5 Hz), 7.36 s (1H, Ar-H), 7.75 d
(2H, Ar-H, J = 8.0 Hz), 7.86 d (2H, Ar-H, J = 8.0 Hz),
8.04 s (1H, triazole-H), 8.38 s (1H, N=CH), 11.86 s
(1H, NH). 13C NMR spectrum, δ, ppm: 48.8, 55.3,
55.7, 67.2, 90.9, 101.2, 109.0, 113.4, 121.9, 125.1,
125.2, 125.4, 127.8, 129.7, 131.5, 132.5, 148.2, 149.3,
149.4, 158.8, 161.1, 162.1. Found, %: С 55.05; Н 4.60;
N 11.48. С28Н28BrN5О6. Calculated, %: С 55.09; Н
4.62; N 11.47. M 610.9 [M + H]+.
(E)-3,4,5-Trimethoxy-N'-{3-methoxy-4-[2-{4-(2,4,6-
trimethoxyphenyl)-1H-1,2,3-triazol-1-yl}ethoxy]benz-
ylidene} benzohydrazide (10d). Off-white solid, yield
80%, mp 89–90°C. IR spectrum, ν, cm–1: 3426 (NH),
1650 (C=O), 1273 (Ar–O). 1H NMR spectrum, δ, ppm:
3.68 br.s (6H, 2OCH3), 3.72 s (3H, OCH3), 3.79 s (3H,
OCH3), 3.82 s (3H, OCH3), 3.86 s (6H, 2OCH3), 4.50
br.s (2H, NCH2), 4.82 br.s (2H, OCH2), 6.30 s (2H,
Ar-H), 7.07 d (1H, Ar-H, J = 8.0 Hz), 7.21 br.s (1H,
Ar-H), 7.22 s (2H, Ar-H), 7.40 s (1H, Ar-H), 8.16 s
(1H, triazole-H), 8.40 s (1H, N=CH), 11.66 s (1H,
NH). 13C NMR spectrum, δ, ppm: 49.0, 55.2, 55.5,
55.6, 55.9, 56.0, 60.0, 67.0, 90.8, 100.8, 105.1, 108.9,
113.3, 121.9, 127.6, 128.2, 128.3, 128.4, 140.3, 147.9,
149.2, 149.3, 152.6, 158.7, 161.1, 161.2, 162.4. Found,
%: С 59.85; Н 5.64; N 11.30. С31Н35N5О9. Calculated,
%: С 59.90; Н 5.67; N 11.27. M 622.4 [M + H]+.
(E)-2-Bromo-N'-{3-methoxy-4-[2-{4-(2,4,6-trimeth-
oxyphenyl)-1H-1,2,3-triazol-1-yl}ethoxy]benzylidene}
benzohydrazide (10b). Pale brown solid, yield 80%,
mp 109–110°C. IR spectrum, ν, cm–1: 3431 (NH),
1657 (C=O), 1266 (Ar–O). 1H NMR spectrum, δ, ppm:
3.66 d.s (3.63*, 6H, 2OCH3), 3.79 d.s (3.57*, 3H,
OCH3), 3.81 d.s (3.59*, 3H, OCH3), 4.47 d.t (4.39*,
2H, J = 4.7 Hz, J = 4.9 Hz, NCH2), 4.78 d.t (4.73*,
2H, J = 4.7 Hz, J = 4.9 Hz, OCH2), 6.29 d.s (6.28*,
2H, Ar-H), 6.92 d.s (6.93*, 1H, Ar-H), 7.05 d (1H, Ar-
H, J = 8.2 Hz), 7.18 d.d (1H, Ar-H, J = 8.2 Hz,
1.1 Hz), 7.35–7.52 m (3H, Ar-H), 7.70 d.d (7.66*, 1H,
Ar-H, J = 7.8 Hz, 7.9 Hz), 8.02 d.s (7.94*, 1H, triazole-
H), 8.17 d.s (7.97*, 1H, N=CH), 11.90 d.s (11.78*,
1H, NH). 13C NMR spectrum, δ, ppm: 49.3, 55.8, 56.1,
56.2, 67.6, 67.8, 91.4, 101.8, 109.5, 110.2, 113.9,
114.2, 119.6, 119.9, 120.7, 122.3, 125.5, 125.6, 127.7,
128.1, 128.2, 128.3, 129.3, 129.7, 130.9, 131.9, 132.3,
133.2, 138.0, 138.8, 139.3, 143.6, 148.3, 149.4, 149.5,
149.8, 149.9, 159.3, 161.6, 163.6, 169.7. Found, %: С
55.07; Н 4.57; N 11.50. С28Н28BrN5О6. Calculated, %:
С 55.09; Н 4.62; N 11.47. M 610.9 [M + H]+.
(E)-N'-{3-Methoxy-4-[2-(4-{2,4,6-trimethoxy-
phenyl}-1H-1,2,3-triazol-1-yl)ethoxy]benzylidene}-
4-nitrobenzohydrazide (10e). Pale yellow solid, yield
79%, mp 210–215°C. IR spectrum, ν, cm–1: 3211
(NH), 1680 (C=O), 1267 (Ar–O). 1H NMR spectrum,
δ, ppm: 3.67 s (6H, 2OCH3), 3.79 s (3H, OCH3), 3.81 s
(3H, OCH3), 4.49 br.s (2H, NCH2), 4.79 br.s (2H,
OCH2), 6.29 s (2H, Ar-H), 7.06 d (1H, Ar-H, J =
7.9 Hz), 7.22 d (1H, Ar-H, J = 7.8 Hz), 7.37 s (1H, Ar-
H), 7.99-8.13 m (3H, triazole-1H, 2Ar-H), 8.35-8.37 m
(3H, N=CH, Ar-H), 12.02 d.s (11.97*, 1H, NH). 13C
NMR spectrum, δ, ppm: 49.4, 49.7, 55.8, 56.1, 56.2,
62.2, 67.7, 91.5, 109.6, 113.9, 121.0, 121.1, 122.5,
124.1, 128.1, 129.6, 139.7, 149.4, 149.7, 149.8, 150.1,
159.3, 161.6. Found, %: С 58.30; Н 4.86; N 14.60.
C28H28N6O8. Calculated, %: С 58.33; Н 4.89; N 14.58.
M 577.26 [M + H]+.
(E)-4-Chloro-N'-{3-methoxy-4-[2-{4-(2,4,6-tri-
methoxyphenyl)-1H-1,2,3-triazol-1-yl}ethoxy]benz-
ylidene} benzohydrazide (10c). Pale yellow solid,
yield 92%, mp 111–112°C. IR spectrum, ν, cm–1: 3444
Synthesis of intermediates 2 and 5. Synthesis of
4-(2-bromoethoxy)-3-methoxybenzaldehyde 2 and 2-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 6 2017