A. Belal, M. A. Abdelgawad
177.24, 178.37; Anal. Calcd. C H N O S (378.41): C, 57.13; H, 3.73; N, 22.21.
Found: 57.30; H, 3.55; N, 22.20.
1
8 14 6 2
N-{4-[(4-Benzoxazol-ylphenyl)hyrazono]-5-oxo-1,5-dihydro-1H-pyrazol-3-yl)
-
1
benzamide (11a) Yield 85%, mp: 220-222°C. IR (cm ): 3226, 3188 (NH), 3043
1
CH aromatic), 1688 (C=O, pyrazolone), 1611 (C=O of amide). H NMR (DMSO,
(
4
7
00 MHz): d 3.21 (s, 1H, NH), 7.35 (dd, J = 8.4 Hz, J = 6.4 Hz, 2H, CH aromatic),
1
2
.42 (dd, J = 8.4 Hz, J = 6.4 Hz, 2H, CH aromatic), 7.44-7.50 (m,, 2H, CH
1
2
aromatic), 7.68 (s,1H, NH), 7.70-7.80 (m, 5H, CH aromatic), 8.15-8.25 (m, 2H, CH
1
3
aromatic), 12.99 (s, 1H, NH); C NMR (DMSO):111.491, 119.60, 120.51, 121.87,
1
1
6
22.43, 122.85 123.15, 125.35, 125.65, 126.35, 129.42, 129.54, 141.95, 154.20,
56.42, 158.78, 161,42, 175.62, 177.73; Anal. Calcd. for C H N O (424.41): C,
5.09; H, 3.80; N, 19.80; Found: 65.20; H, 3.95; N, 20.10.
2
3 16 6 3
N-{4-[(4-Benzothiazol-ylphenyl)hyrazono]-5-oxo-1,5-dihydro-1H-pyrazol-3-yl)
-
1
benzamide (11b) Yield 87%, mp: 230-232°C. IR (cm ): 3203 (NH), 3056 (CH
aromatic), 1678 (C=O, pyrazolone), 1647 (C=O of amide);. H NMR (DMSO, 400
1
MHz): d 3.19 (s, 1H, NH), 7.32 (dd, J = 9.2 Hz, J = 6.8 Hz, 2H, CH aromatic), 7.44
1
2
(
dd, J = 9.2 Hz, J = 6.8Hz, 2H, CH aromatic), 7.46-7.50 (m, 2H, CH aromatic),
1 2
7
8
1
1
3
.70 (s, 1H, NH),7.94-8.04 (m, 5H, CH aromatic), 8.12-8.18 (m, 2H, CH aromatic),
1
3
.22 (s, 1H, NH). C NMR (DMSO):115.45, 117.37, 120.54, 122.83, 123.23,
24.54, 124.87, 126.03, 126.49, 127.75, 129.08, 130.03, 141.95, 152.89, 153.34,
57.57, 160,41, 170.89, 175.37. Anal. Calcd. for C H N O (440.48): C, 62.72; H,
23 16 6 3
.66; N, 19.08; Found: 62.80; H, 3.55; N, 19.35.
N-{4-[(4-Benzoxazol-ylphenyl)hyrazono]-5-oxo-4,5-dihydro-1H-pyrazol-3-yl)2-
-
1
chloroacetamide (12a) Yield 79%, mp: 192-194°C. IR (cm ): 3397, 3140 (NH),
046 (CH aromatic), 2921 (CH aliph), 1684 (C=O pyrazolone),1649(C=O of
3
1
amide). H NMR (DMSO, 400 MHz): d 3.41 (s, 1H, NH), 3.87 (s, 2H, CH ), 7.36
2
(
dd, J = 8.4 Hz, J = 11.2 Hz, 2H, CH aromatic), 7.42 (dd, J = 8.4 Hz, J = 11.2Hz,
1 2 1 2
2
2
1
1
H, CH aromatic), 7.69 (s, 1H, NH), 7.71-7.78 (m, 2H, CH aromatic), 8.15-8.24 (m,
1
3
H, CH aromatic), 8.26 (s, 1H, NH). C NMR (DMSO): 40.59, 111.37, 120.20,
20.53, 123.40, 125.40, 125.97,129.30, 129.53, 141.97, 143.51, 150.65, 162.17,
63,34, 176.14, 175.73. Anal. Calcd. for C H ClN O (396.79): C, 54.49; H, 3.30;
1
8
13
6 3
N, 21.18. Found: 54.40; H, 3.35; N, 21.10.
N-{4-[(4-Benzothiazol-ylphenyl)hyrazono]-5-oxo-4,5-dihydro-1H-pyrazol-3-yl)2-
-
1
chloroacetamide (12b) Yield 85%, mp: 195-197°C. IR (cm ): 3392, 3138 (NH),
046 (CH aromatic), 2921 (CH aliph), 1673 (C=O pyrazolone), 1648 (C=O of
3
1
amide). H NMR (DMSO, 400 MHz): d 3.41 (s, 1H, NH), 3.88 (s, 2H, CH ), 7.32
2
(dd, J = 8.8 Hz, J = 6 Hz, 2H, CH aromatic), 7.44 (dd, J = 8.8 Hz, J = 6 Hz, 2H,
1 2 1 2
CH aromatic), 7.57 (s, 1H, NH), 7.81–7.93 (m, 2H, CH aromatic), 8.10–8.16 (m,
1
3
2
1
1
3
H, CH aromatic), 8.18 (s, 1H, NH). C NMR (DMSO): 40.53, 111.50, 120.54,
22.85, 123.25, 126.01, 127.20, 129.37, 130.04, 134.86, 142.88, 154.01, 166.81,
67,34, 175.12, 177.74; Anal. Calcd. for C H ClN O S (412.85): C, 52.37; H,
1
8
13
6 2
.17; N, 20.36. Found: 52.30; H, 3.10; N, 20.20.
1
23