158 M. Ashraf Ali et al.
12 h and cooled. e progress of the reaction was moni-
tored by TLC and after completion of the reaction, the
solvent was evaporated by vacuo and the reaction mix-
ture was poured on to crushed ice (20 gm). e product
obtained was filtered and washed with water and then
recrystallized from methanol.
Aromatic); 7.4–8.50 (4H, m, pyridine); Mass (m/z) 434
(M+1); Cal/Ana [C(66.44) 66.42, H(4.65) 4.63, N(9.688)
9.66].
1 - [ 6 , 7 - d i m e t h o x y - 3 - ( 4 -p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl-4-methylphenyl
methanone(4g) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1
6,
7-dimethoxy-3-(4-pyridyl)-2,3,3a,4-
metha-
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ1.72
tetrahydroindeno[1,2-c]pyrazol-2-yl-phenyl
(3H, s, CH3) 2.1–2.4 (2H, m, CH2), 2.5–2.6 (1H, m,
CH-Indane), 3.6 (6H, s, OCH3), 5.5 (1H, d, pyrazoline-CH),
6.60–7.10 (6H, m, Aromatic); 7.4–8.50 (4H, m, pyridine);
Mass (m/z) 414 (M+1); Cal/Ana [C(72.62) 72.60, H(5.61)
5.60, N(10.16) 10.14].
none (4a) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O), 1439
(C=C), 766 (C-F). 1HNMR(DMSO-d6, ppm): δ2.1–2.4
(2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.6 (6H, s,
OCH3), 5.5 (1H, d, pyrazoline-CH), 6.60–7.10 (7H, m,
Aromatic);7.4–8.50 (4H, m, pyridine); Mass (m/z) 400
(M+1); Cal/Ana [C(72.17) 72.10, H(5.30) 5.29, N(10.52)
10.50].
1 - [ 6 , 7 - d i m e t h o x y - 3 - ( 4 -p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl-4-pyridyl
methanone(4h) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1
4-bromophenyl-6,7-dimethoxy-3-(4-pyridyl)-
2, 3, 3a, 4-tetrahydroindeno[1, 2-c]pyrazol-2-yl
methanone(4b) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ1.72
(3H, s, CH3), 2.1–2.4 (2H, m, CH2), 2.5–2.6 (1H, m,
CH-Indane), 3.6 (6H, s, OCH3), 5.5 (1H, d, pyrazoline-CH),
6.60–7.10 (2H, m, Aromatic); 7.4–8.50 (8H, m, pyridine);
Mass (m/z) 401 (M+1); Cal/Ana [C(68.99) 68.97, H(5.03)
5.01, N(13.99) 13.97].
1
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ2.1–
2.4 (2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.6 (6H,
s, OCH3), 5.5 (1H, d, pyrazoline-CH), 6.60–7.10 (6H, m,
Aromatic); 7.4–8.50 (4H, m, pyridine); Mass (m/z) 479
(M+1); Cal/Ana [C(60.26) 60.24, H(4.21) 4.20, N(8.78)
8.76].
1 - [ 6 , 7 - d i m e t h o x y - 3 - ( 4 -p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl-2-methylphenyl
methanone(4i) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1
4-fluorophenyl-6,7-dimethoxy-3-(4-pyridyl)-2-
, 3, 3a, 4-tetrahydroindeno[1, 2-c]pyrazol-2-yl-
methanone(4c) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ1.72
(3H, s, CH3) 2.1–2.4 (2H, m, CH2), 2.5–2.6 (1H, m,
CH-Indane), 3.6 (6H, s, OCH3), 5.5 (1H, d, pyrazoline-CH),
6.60–7.10 (6H, m, Aromatic); 7.4–8.50 (4H, m, pyridine);
Mass (m/z) 414 (M+1); Cal/Ana [C(72.62) 72.60, H(5.61)
5.60, N(10.16) 10.14].
1 - [ 6 , 7 - d i m e t h o x y - 3 - ( 4 -p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl]-2-phenyl-1-
ethanone(4j) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O), 1439
(C=C), 766 (C-F). 1H-NMR (DMSO-d6, ppm): δ2.1–2.4
(2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.2 (2H, m,
benzyl-CH2),3.6(6H,s,OCH3),5.5(1H,d,pyrazoline-CH),
6.60–7.10 (6H, m, Aromatic); 7.4–8.50 (4H, m, pyridine);
Mass (m/z) 414 (M+1); Cal/Ana [C(72.62) 72.60, H(5.61)
5.60, N(10.16) 10.14].
1 - [ 6 , 7 - d i m e t h o x y - 3 - ( 4 -p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl]-2-phenoxy-1-
ethanone(4k) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O), 1439
(C=C), 766 (C-F). 1HNMR(DMSO-d6, ppm): δ2.1–2.4 (2H,
m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.2 (2H, m, phe-
oxy-CH2), 3.6 (6H, s, OCH3), 5.5 (1H, d, pyrazoline-CH),
6.60–7.10 (6H, m, Aromatic); 7.4–8.50 (4H, m, pyridine);
Mass (m/z) 430M+1); Cal/Ana [C(69.92) 69.90, H(5.40)
5.38, N(9.78) 9.76].
1
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ2.1–
2.4 (2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.6 (6H,
s, OCH3), 5.5 (1H, d, pyrazoline-CH), 6.60–7.10 (6H, m,
Aromatic); 7.4–8.50 (4H, m, pyridine); Mass (m/z) 418
(M+1); Cal/Ana [C(60.06) 69.04, H(4.83) 4.81, N(10.07)
10.09].
6 , 7 - d i m e t h o x y - 3 - ( 4 - p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl-4-nitrophenyl
methanone(4d) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ2.1–
2.4 (2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.6 (6H,
s, OCH3), 5.5 (1H, d, pyrazoline-CH), 6.60–7.10 (6H, m,
Aromatic); 7.4–8.50 (4H, m, pyridine); Mass (m/z) 445
(M+1); Cal/Ana [C(68.86) 68.88, H(4.54) 4.52, N(12.61)
12.63].
2-chlorophenyl-6,7-dimethoxy-3-(4-pyridyl)-
2, 3, 3a, 4-tetrahydroindeno[1, 2-c]pyrazol-2-yl
methanone(4e) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ2.1–
2.4 (2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.6 (6H,
s, OCH3), 5.5 (1H, d, pyrazoline-CH), 6.60–7.10 (6H, m,
Aromatic); 7.4–8.50 (4H, m, pyridine); Mass (m/z) 434
(M+1); Cal/Ana [C(66.44) 66.42, H(4.65) 4.63, N (9.688)
9.66].
1 - [ 6 , 7 - d i m e t h o x y - 3 - ( 4 -p y r i d y l ) - 2 , 3 , 3 a , 4 -
tetrahydroindeno[1,2-c]pyrazol-2-yl-4-methoxyphenyl
methanone(4l) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1
4-chlorophenyl-6,7-dimethoxy-3-(4-pyridyl)-
2, 3, 3a, 4-tetrahydroindeno[1, 2-c]pyrazol-2-yl
methanone(4f) IR:(KBr, cm−1): 3042 (CH), 1642 (C=O),
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ2.1–
2.4(2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), CH2), 3.6
(9H, s, OCH3), 5.5(1H, d, pyrazoline-CH), 6.60–7.10
(6H, m, Aromatic); 7.4–8.50 (4H, m, pyridine); Mass
(m/z) 430M+1); Cal/Ana [C(69.92) 69.90, H(5.40) 5.38,
N(9.78) 9.76].
1
1439 (C=C), 766 (C-F). HNMR(DMSO-d6, ppm): δ2.1–
2.4 (2H, m, CH2), 2.5–2.6 (1H, m, CH-Indane), 3.6 (6H,
s, OCH3), 5.5 (1H, d, pyrazoline-CH), 6.60–7.10 (6H, m,
Journal of Enzyme Inhibition and Medicinal Chemistry