2
934
REDDY et al., Orient. J. Chem., Vol. 33(6), 2930-2936 (2017)
3
6
7
.85 (s, 3H), 3.88 (* 3.72, s, 2H), 5.60 (s, 2H), 6.95- (E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-
.84 (broad multiplet, 5H), 7.30 (t, J = 8.1 Hz, 1H), 1,2,3-triazol-4-yl)benzylidene)benzohydrazide
.70 (d, J = 8.2 Hz, 2H), 7.92 (d, J = 7.8 Hz, 2H), 8.20 (44)
o
(s, 1H), 8.36 (*8.35, s, 1H), 11.50 (* 11.33, s, 1H);
Off-white solid; M.p.: 108-109 C; IR (KBr):
υmax 3437 (-CONH, stretching), 1655 (-C=O,
stretching), 1616 (-C=N, stretching), 1368 (-C-N,
+
ESI-MS: m/z, 664.1 (M+H) .
-
1
1
(
E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H- stretching), 1084 (-C-O-C, stretching) cm ; H NMR
1
,2,3-triazol-4-yl)benzylidene)-2-(2-chloro-4- (400 MHz, DMSO-d ): δ 0.83 (t, J = 6.8 Hz, 3H), 1.33-
6
fluorophenyl) acetohydrazide (41)
1.14 (brm, 26H), 2.71 (t, J = 7.2 Hz, 2H), 3.86 (s,
o
Pale yellow solid; M.p.: 96-98 C; IR (KBr): 3H), 5.60 (s, 2H), 6.84 (d, J = 8.0 Hz, 2H), 6.90 (d, J
υmax 3199 (-CONH, stretching), 1657 (-C=O, = 8.0 Hz, 2H), 7.06 (d, J = 8.8 Hz, 2H), 7.22 (d, J =
stretching), 1608 (-C=N, stretching), 1370 (-C-N, 8.0 Hz, 1H), 7.72-7.64 (m, 7H), 7.86 (t, J = 7.2 Hz,
-
1 1
stretching), 1069 (-C-O-C, stretching) cm ; H NMR 2H), 8.30 (s, 1H), 8.42 (s, 1H), 11.68 (s, 1H); ESI-
+
(
(
(
300 MHz, DMSO-d ): δ 0.83 (brs, 3H), 1.35-1.15 MS: m/z, 622.4 (M+H) .
broad multiplet, 26H), 2.72 (t, J = 6.9 Hz, 2H), 3.85
s, 3H), 4.14 (* 3.72, s, 2H), 5.60 (s, 2H), 6.84 (d, J = (E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-
6
7
.2 Hz, 1H), 6.94 (d, J = 7.8 Hz, 1H), 7.49-7.16 1,2,3-triazol-4-yl)benzylidene)-4-methoxy-
(
(
1
series.multiplet, 4H), 7.71 (d, J = 7.8 Hz, 2H), 7.91 benzohydrazide (45)
o
d, J = 7.8 Hz, 2H), 8.02 (s, 1H), 8.35 (*8.21, s, 1H),
1.64 (* 11.51, s, 1H); ESI-MS: m/z, 688.3 (M+H) .
Off-white solid; M.p.: 131-133 C; IR (KBr):
υmax 3286 (-CONH, stretching ),1658 (-C=O,
stretching), 1605 (-C=N, stretching),1349 (-C-N,
+
-
1 1
(
1
E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H- stretching), 1084 (C-O-C, stretching) cm ; H NMR
,2,3-triazol-4-yl)benzylidene)-2-(4-nitrophenyl) (400 MHz, DMSO-d ): δ 0.81 (t, J = 6.8 Hz, 3H),
6
acetohydrazide (42)
1.33-1.14 (brm, 26H), 2.71 (t, J = 7.2 Hz, 2H), 3.84
(s, 6H), 5.60 (s, 2H), 6.85 (d, J = 8.0 Hz, 2H), 6.93 (d,
o
Yellow solid;M.p.:120-121 C;IR (KBr):υ
max
3
1
1
196 (-CONH, stretching), 1651 (-C=O, stretching), J = 8.0 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 7.28 (t, J =
.0 Hz, 1H), 7.73-7.68 (m, 2H), 7.90 (t, J = 7.2 Hz,
8
609 (-C=N, stretching), 1370 (-C-N, stretching),
-
1
1
2H), 8.33 (s, 1H), 8.44 (s, 1H), 11.72 (s, 1H); ESI-
MS: m/z, 652.4 (M+H) .
088 (-C-O-C, stretching) cm ; H NMR (300 MHz,
+
DMSO-d ): δ 0.83 (t, J = 5.4 Hz, 3H), 1.35-1.15 (m,
6
2
3
6
6H), 2.73 (t, J = 6.6 Hz, 2H), 3.85 (s, 3H), 4.18 (*
.74, s, 2H), 5.60 (s, 2H), 6.86 (d, J = 8.1 Hz, 1H),
.94 (d, J = 8.4 Hz, 1H), 7.30 (t, J = 7.5 Hz, 1H), 7.60
(
1
E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-
,2,3-triazol-4-yl)benzylidene)-4-chloroben-
zohydrazide (46)
(
d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.1 Hz, 2H), 7.92 (d,
o
Pale yellow solid; M.p.: 122-123 C; IR (KBr):
υmax 3289 (-CONH, stretching ), 1661 (-C=O,
stretching), 1602 (-C=N, stretching), 1273 (-C-N,
J = 8.1 Hz, 2H), 8.05 (s, 1H), 8.20 (d, J = 6.9 Hz, 2H),
8.36 (*8.22, s, 1H), 11.69 (* 11.53, s, 1H); ESI-MS:
+
m/z, 681.3 (M+H) .
-1 1
stretching), 1085 (-C-O-C, stretching) cm ; H NMR
(
1
5
400 MHz, DMSO-d ): δ 0.81 (t, J = 6.6 Hz, 3H), 1.33-
.13 (m, 26H), 2.71 (t, J = 7.2 Hz, 2H), 3.84 (s, 3H),
.60 (s, 2H), 6.83 (d, J = 7.8 Hz, 1H), 6.93 (d, J = 7.8
6
(
1
5
E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-
,2,3-triazol-4-yl)benzylidene)-2-(2,3-dihydrobenzofuran-
-yl)acetohydrazide (43)
Off-white solid; M.p.: 131-132 C; H NMR
300 MHz, DMSO-d ): δ 0.84 (t, J = 6.8 Hz, 3H),
Hz, 1H), 7.29 (t, J = 7.2 Hz, 1H), 7.58 (d, J = 7.6 Hz,
H), 7.80 (d, J = 7.6 Hz, 2H), 7.93 (d, J = 8.0 Hz, 3H),
o
1
2
(
6
8.38 (s, 1H), 8.44 (s, 1H), 11.85 (s, 1H),; ESI-MS: m/
z, 656.3 (M+H) .
1
.35-1.15 (m, 26H), 2.73 (t, J = 6.8 Hz, 2H), 3.15 (t,
J = 5.8 Hz, 2H), 3.85 (s, 3H), 3.87 (* 3.50, s, 2H),
.50 (t, J = 5.7 Hz, 2H), 5.60 (s, 2H), 6.67 (t, J = 8.4
Hz, 1H), 6.86 (d, J = 7.8 Hz, 1H), 6.94 (d, J = 8.7 Hz,
+
4
(
E)-N’-(4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-
,2,3-triazol-4-yl)benzylidene)-4-fluoroben-
zohydrazide (47)
1
1
H), 7.0 (d, J = 8.7 Hz, 1H), 7.15 (s, 1H), 7.32 (t, J =
.8 Hz, 1H), 7.74 (d, J = 8.1 Hz, 2H), 7.93 (d, J = 8.0
7
o
1
Pale yellow solid; M.p.: 128-129 C; H NMR
Hz, 2H), 8.35 (*8.20, s, 1H), 11.51 (* 11.31, s, 1H);
ESI-MS: m/z, 678.1 (M+H) .
(400 MHz, DMSO-d ): δ 0.82 (t, J = 6.6 Hz, 3H), 1.33-
6
+
1
.12 (m, 26H), 2.71 (t, J = 7.2 Hz, 2H), 3.85 (s, 3H),