Arch. Pharm. Chem. Life Sci. 2016, 349, 383–397
S. K. Krishnasamy et al.
ARC HH PHARM
Archiv der Pharmazie
1
32.9, 130.9, 128.9, 128.2, 127.9, 123.8, 121.3, 70.1, 54.3; MS:
2-[2-(2,4-Dimethoxybenzylidene)hydrazinyl]-N-(5-oxo-1-
þ
m/z 335.14 [M] ; Anal. (C18
H
17
5
N O
2
) C, H, N.
phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7g)
ꢀ
1
IR (KBr) cm : 3437 (NH str), 1653 (C–N str), 1601 (C–C str),
1
2
4
-[2-(4-Chlorobenzylidene)hydrazinyl]-N-(5-oxo-1-phenyl-
1513 (CONH); H NMR (DMSO-d
6
) d ppm: 10.51 (2H, bs, 2NH,
,5-dihydro-1H-pyrazol-3-yl)acetamide (7b)
D
2
O exchangeable), 8.8 (s, 1H, –CH), 6.4–7.9 (8H, m, Ar–H), 3.9
(2H, d, COCH ), 3.5 (6H, d, OCH ), 2.81 (2H, s, CH pyrazolone);
C NMR (DMSO-d ) d ppm: 174.2, 172.8, 162.8, 161.2, 154.2,
ꢀ
1
IR (KBr) cm : 3536 (NH str), 2942 (Ar C–H str), 1559 (NH–C–O
2
3
2
1
13
str), 1089 (C–Cl str); H NMR (DMSO-d
6
) d ppm: 10.61 (2H, bs,
6
2
NH, D
2
O exchangeable), 8.72 (s, 1H, –CH), 6.8–8.2 (9H, m,
), 2.8 (3H, s, CH pyrazolone);
) d ppm: 175.6, 173.1, 153.9, 143.1, 140.1,
143.2, 140.3, 130.9, 130.1, 129.8, 124.3, 121.8, 121.1, 110.1,
107.1, 102.4, 69.1, 56.4, 56.1, 54.1; MS: m/z 395.16 [M] ; Anal.
(C20H N O ) C, H, N.
21 5 4
þ
Ar–H), 3.76 (2H, d, COCH
2
2
13
C NMR (DMSO-d
6
1
1
34.4, 129.8, 129.5, 129.3, 128.6, 128.4, 128.3, 128.0, 124.5,
22.4, 122.1, 71.1, 53.9; MS: m/z 369.10 [M] ; Anal.
þ
2-{2-[1-(4-Chlorophenyl)ethylidene]hydrazinyl}-N-(5-oxo-
(
C
18
H
16ClN
5
O
2
) C, H, N.
1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7h)
ꢀ
1
IR (KBr) cm : 3385 (NH str), 2924 (Ar C–H str), 1607 (C–C str),
1
2
-[2-(2,4-Dichlorobenzylidene)hydrazinyl]-N-(5-oxo-1-
1091 (Ar C–Cl str); H NMR (DMSO-d
6
) d ppm: 10.65 (2H, bs,
phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7c)
2NH, D
COCH ), 2.85 (2H, s, CH
6
(DMSO-d ) d ppm: 174.4, 172.9, 168.9, 154.3, 141.2, 136.6,
2
O exchangeable), 6.7–8.2 (9H, m, Ar–H), 3.86 (2H, d,
ꢀ1
1
13
IR (KBr) cm : 3588 (NH str), 1601 (C–O str); H NMR (DMSO-
) d ppm: 10.58 (2H, bs, 2NH, D O exchangeable), 8.54 (s, 1H,
CH), 6.6–8.1 (8H, m, Ar–H), 3.62 (2H, d, COCH ), 2.6 (2H, s, CH
3
pyrazolone), 2.1 (3H, s, CH ); C NMR
2
2
d
6
2
–
133.1, 129.5, 129.4, 129.1, 128.8, 128.5, 128.3, 124.6, 121.4,
–
2
2
13
þ
pyrazolone); C NMR (DMSO-d
6
) d ppm: 175.4, 172.9, 154.1,
121.1, 69.1, 54.9, 14.8; MS: m/z 383.11 [M] ; Anal.
1
1
43.3, 140.2, 134.6, 129.8, 129.5, 129.4, 128.7, 128.3, 128.1,
27.9, 125.2, 122.4, 122.1, 71.1, 53.9; MS: m/z 403.06 [M] ;
(C19H N
18 5
O
2
Cl) C, H, N.
þ
15 5 2 2
Anal. (C18H N O Cl ) C, H, N.
2-{2-[1-(4-Fluorophenyl)ethylidene]hydrazinyl}-N-(5-oxo-
1
-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7i)
ꢀ1
2
-{2-[1-(Furan-3-yl)ethylidene]hydrazinyl}-N-(5-oxo-1-
IR (KBr) cm : 3437 (NH str), 1595 (NHCO–R), 1496 (C–C ring
1
phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7d)
str), 964 (C–F str); H NMR (DMSO-d
6
) d ppm: 10.49 (2H, bs,
ꢀ
1
IR (KBr) cm : 3406 (NH str), 2923 (Ar C–H str), 1582 (NHCO–R),
2NH, D
COCH ), 2.76 (2H, s, CH
6
(DMSO-d ) d ppm: 174.9, 172.5 167.8, 154.9, 141.1, 136.2,
2
O exchangeable), 6.6–8.1 (9H, m, Ar–H), 3.83 (2H, d,
1
13
1
138 (C–O str); H NMR (DMSO-d
O exchangeable), 8.7 (s, 1H, –CH), 6.2–7.6 (8H, m, 3H furan
and 5H Ar), 3.89 (2H, d, COCH ), 2.65 (2H, s, CH pyrazolone);
) d ppm: 175.3, 173.9, 153.2, 148.2, 143.4,
6
) d ppm: 10.55 (2H, bs, 2NH,
2
2
3
pyrazolone), 2.1 (3H, s, CH ); C NMR
D
2
2
2
133.6, 129.8, 129.5, 129.2, 128.8, 128.5, 128.2, 124.5, 121.6,
13
þ
C NMR (DMSO-d
6
121.3, 69.5, 55.9, 14.2; MS: m/z 367.14 [M] ; Anal.
1
6
39.7, 135.2, 129.9, 129.6, 124.3, 120.9, 120.5, 111.4, 110.1,
(C19H N
18 5
O
2
F) C, H, N.
þ
9.5, 54.7; MS: m/z 325.12 [M] ; Anal. (C16
H
15
5
N O
3
) C, H, N.
2-{2-[1-(2-Hydroxyphenyl)ethylidene]hydrazinyl}-N-(5-
2
-[2-(2-Hydroxybenzylidene)hydrazinyl]-N-(5-oxo-1-
oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7j)
ꢀ
1
phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7e)
IR (KBr) cm : 3796 (NH str), 3392 (OH bend), 1607 (C–C str),
IR (KBr) cm : 3400 (NH str), 2923 (OH bend), 1603 (C–C str);
ꢀ
1
1
6 2
H NMR (DMSO-d ) d ppm: 10.69 (2H, bs, 2NH, D O
1
1
507 (C–N str); H NMR (DMSO-d
6
) d ppm: 10.61 (2H, bs, 2NH,
exchangeable), 9.8 (1H, s, Ar–OH), 6.6–7.8 (4H, m, Ar–H),
3.79 (2H, d, COCH ), 2.76 (2H, s, CH pyrazolone), 2.3 (3H, s,
); C NMR (DMSO-d ) d ppm: 174.2, 172.9, 167.2, 162.1,
D
2
O exchangeable), 8.9 (1H, s, Ar–OH), 8.1 (s, 1H, –CH), 6.3–7.7
9H, m, Ar–H), 3.69 (2H, d, COCH ), 2.72 (2H, s, CH
) d ppm: 174.4, 172.9,
2
2
1
3
(
2
2
CH
3
6
13
pyrazolone);
C NMR (DMSO-d
6
155.1, 141.0, 133.2, 130.8, 129.9, 129.5, 124.2, 121.8, 121.5,
þ
1
1
60.9, 154.3, 143.2, 140.6, 133.8, 129.5, 129.4, 129.2, 124.9,
22.1, 121.9, 121.6, 119.4, 115.1, 69.1, 54.9; MS: m/z 351.13
121.2, 119.5, 116.6, 69.3, 55.6, 14.9; MS: m/z 365.15 [M] ; Anal.
(C19H N
19 5
O
3
) C, H, N.
þ
[
M] ; Anal. (C18
H N
17 5
O
3
) C, H, N.
2
-{2-[1-(4-Nitrophenyl)ethylidene]hydrazinyl}-N-(5-
2
-[2-(4-Methoxybenzylidene)hydrazinyl]-N-(5-oxo-1-
oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide
phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetamide (7f)
(7k)
ꢀ1
ꢀ1
IR (KBr) cm : 3654 (NH str), 1683 (C–N str), 1567 (NHCO–R),
IR (KBr) cm : 3675 (NH str), 1684 (C–N str), 1558 (NHCO–R str),
1
1
1
2
253 (C–O–C str); H NMR (DMSO-d
6
) d ppm: 10.68 (2H, bs,
1521 (NO str); H NMR (DMSO-d
6
) d ppm: 10.76 (2H, bs, 2NH,
NH, D
2
O exchangeable), 8.6 (s, 1H, –CH), 6.3–8.1 (9H, m,
), 3.1 (3H, s, OCH ), 2.62 (2H, s, CH
pyrazolone); C NMR (DMSO-d ) d ppm: 174.2, 172.6, 162.9,
54.2, 143.1, 140.2, 130.8, 130.5, 129.4, 129.2, 126.0, 123.1,
D
2
O exchangeable), 6.8–8.2 (4H, m, Ar–H), 3.75 (2H, d,
COCH ), 2.65 (2H, s, CH pyrazolone), 2.1 (3H, s, CH );
C NMR (DMSO-d ) d ppm: 174.4, 172.3, 168.4, 155.6,
Ar–H), 3.8 (2H, d, COCH
2
3
2
2
2
3
13
13
6
6
1
1
151.1, 141.0, 140.2, 130.4, 129.9, 129.6, 129.0, 124.5, 121.6,
121.1, 120.8, 120.7, 69.5, 55.2, 14.6; MS: m/z 394.14 [M] ; Anal.
(C19H N O ) C, H, N.
18 6 4
þ
21.9, 121.6, 115.4, 115.1, 69.1, 56.4, 54.1; MS: m/z 365.15
þ
[
M] ; Anal. (C19H N
19 5
O
3
) C, H, N.
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