ACCEPTED MANUSCRIPT
C -H); 7.08-7.25 (m, 3H, hydroxyphenyl-C -H); 7.38 (t, J = 7.35 Hz, 1H, phenyl-C -H);
3
,5
2,5,6
4
7
.54-7.59 (m, 2H, phenyl-C3,5-H); 7.83 (d, J = 9 Hz, 2H, methoxyphenyl-C2,6-H); 7.92 (d, J =
7
.8 Hz, 2H, phenyl-C -H); 8.19 (s, 1H, pyrazole-C -H); 8.99 (s, 1H, -CH=N); 9.6 (s, 1H, OH,
2
,6
5
D
2
O-exchangeable); 11.99 (s, 1H, NH, D
2
O-exchangeable). Elemental analysis Calcd for
C H N O : C, 69.89; H, 4.89; N, 13.58. Found: C, 70.12; H, 4.96; N, 13.79.
24
20
4
3
5
.1.4.4 N'-(4-Fluorobenzylidene)-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-4-
carbohydrazide 4d
0
-1
The product was obtained as white solid, mp 223-225 C, in yield (66%). IR (cm ): 3185
NH); 1660 (C=O); 1603 (C=N). H -NMR (300 MHz, DMSO-d , δ ppm): 3.80 (s, 3H,
6
1
(
OCH ); 7.00 (d, J = 8.7 Hz, 2H, methoxyphenyl-C -H); 7 (m, 2H, fluorophenyl-C -H); 7.38
3
3,5
3,5
4
(t, J = 7.35 Hz, 1H, phenyl-C -H); 7.54-7.59 (m, 2H, phenyl-C3,5-H); 7.8-7.84 (m, 4H,
methoxyphenyl-C -H and fluorophenyl-C -H); 7.92 (d, J = 7.8 Hz, 2H, phenyl-C -H); 8.29
2
,6
2,6
2,6
(
s, 1H, pyrazole-C
5
-H); 8.99 (s, 1H, -CH=N); 11.77 (s, 1H, NH, D
2
O-exchangeable). EIMS
+
·
+·
m/z (% relative abundance): 415 (4) (M +1), 414 (12) (M ), 293 (16), 278 (20), 277 (100),
2
6
34 (5), 145 (6), 104 (9), 77 (16), 75 (21). Elemental analysis Calcd for C24
9.55; H, 4.62; N, 13.52. Found: C, 69.81; H, 4.67; N, 13.74.
4 2
H19FN O : C,
5
.1.4.5 3-(4-Methoxyphenyl)-1-phenyl-N'-(thiophen-2-ylmethylene)-1H-pyrazole-4-
carbohydrazide 4e
0
-1
The product was obtained as white solid, mp 213-215 C, in yield (62%). IR (cm ): 3173
1
6
(NH); 1654 (C=O); 1600 (C=N); 1058 (C-S-C). H -NMR (DMSO-d , δ ppm): 3.80 (s, 3H,
OCH ); 7.00 (d, J = 8.25 Hz, 2H, methoxyphenyl-C -H); 7.13 (m, 1H, thiophen-C -H); 7.42
3
3,5
4
4
(t, J = 7.35 Hz, 1H, phenyl-C -H); 7.46-7.67 (m, 4H, phenyl-C3,5-H, thiophen-C3,5-H); 7.82 (d,
J = 8.25 Hz, 2H, methoxyphenyl-C -H); 7.92 (d, J = 7.7 Hz, 2H, phenyl-C -H); 8.50 (s, 1H,
2
,6
2,6
pyrazole- C
5
-H); 8.96 (s,1H, -CH=N); 11.64 (s, 1H, NH, D
2
O-exchangeable). Elemental
analysis Calcd for C H N O S: C, 65.65; H, 4.51; N, 13.92; S, 7.97. Found: C, 65.89; H,
2
2
18
4
2
4
.54; N, 14.15; S, 8.04.
5
.1.4.6 3-(4-Methoxyphenyl)-1-phenyl-N'-(pyridin-4-ylmethylene)-1H-pyrazole-4-
carbohydrazide 4f
0
-1
The product was obtained as white solid, mp 198-200 C, in yield (70%). IR (cm ): 3181
NH); 1664 (C=O); 1590 (C=N). H -NMR (DMSO-d , δ ppm): 3.78 (s, 3H, OCH ); 6.98 (d, J
1
(
6
3
=
8.7 Hz, 2H, methoxyphenyl-C3,5-H); 7.37 (m, 1H, phenyl-C
4
-H); 7.53-7.65 (m, 4H, phenyl-
C2,3,5,6-H); 7.79 (d, J = 8.7 Hz, 2H, methoxyphenyl-C -H); 7.90 (d, J = 8.7 Hz, 2H, pyridine-
2,6
C
5
2,6-H); 8.26 (s, 1H, pyrazole-C -H); 8.63 (d, J = 8.7 Hz, pyridine-C2,6-H); 9.02 (s, 1H, -
1
3
CH=N); 11.99 (s, 1H, NH, D O-exchangeable). C-NMR (DMSO-d , δ ppm): 55.70 (OCH );
2
6
3
1
1
4
14.15 (methoxyphenyl-C3,5 and pyrazole-C ); 119.21 (phenyl-C2,6); 121.49 (pyridine-C2,6);
25.32 (methoxyphenyl-C ); 127.60 (phenyl-C ); 130.06 (methoxy phenyl-C ); 130.29
1
4
2,6
(phenyl-C3,5); 131.26 (pyrazole-C
5
1 1
); 139.50 (phenyl-C ); 144.77 (pyridine-C ); 146.80
1
9