Pyrazoles and Pyrazolo[3,4-b]pyridines
J. Chin. Chem. Soc., Vol. 54, No. 2, 2007 513
Table 1. Spectral data of the new compounds
Compd.
IR, n (cm-1)
No
1H NMR (d)
2
3330 (NH), 3050 (CH arom.), 2990 (CH
aliph.)
2.35 (s, 3H, CH3), 6.55 (s, 1H, CH-pyrazole), 7.35-7.85 (m,
10H, arom), 10.5 (s, 1H, NH)
3a
3b
3c
4
3300-3180 (NH2), 3040 (CH arom.), 2980
(CH aliph.)
2.40 (s, 3H, CH3), 5.6 (s, 2H, NH2), 7.03-7.55 (m, 10H, arom.)
3320-3220 (NH2), 3060 (CH arom.), 2990
(CH aliph.)
2.30 (s, 3H, CH3), 2.40 (s, 3H, CH3), 5.50 (s, 2H, NH2), 7.2-7.65
(m, 9H, arom.)
3310-3190 (NH2), 3050 (CH arom.), 2980
(CH aliph.)
2.40 (s, 3H, CH3), 2.60 (s, 3H, -OCH3), 4.90 (s, 2H, NH2), 7.10-
7.75 (m, 9H, arom.)
3250 (NH), 3050 (CH arom.), 2980, 2990
(CH aliph.), 1710 (CO)
2.30 (s, 3H, CH3), 4.15 (s, 2H, CH2), 6.5 (s, 1H, CH-pyrazole),
7.55-8.05 (m, 5H, arom.), 8.6 (1H, NH)
5a
5b
3330 (NH), 3050 (CH arom), 2990 (CH
aliph.), 2200 (CN)
2.40 (s, 3H, CH3), 6.55 (s, 1H, CH-pyrazole), 7.35-7.60 (m, 5H,
arom.), 7.75 (s, 1H, CH), 10.60 (s, H, NH)
1.30 (t, 3H, CH3), 2.30 (s, 3H, CH3), 4.10 (q, 2H, CH2), 6.75 (s,
1H, CH-pyrazole), 7.30-7.60 (m, 5H, arom.), 7.73 (s, 1H, CH-
ethylenic), 10.6 (s, 1H, NH)
3260 (NH), 3050 (CH arom.), 2990, 2980
(CH aliph.), 2210 (CN), 1690 (CO)
6
3280 (NH), 3050 (CH arom), 2995 (CH
aliph.), 2210 (CN), 1700 (CO)
3050 (CH arom.), 2990 (CH aliph.), 2200
(CN)
2.35 (s, 3H, CH3), 7.35-7.60 (m, 5H, arom), 7.95 (s, 1H, CH-
pyridine), 10.10 (s, H, NH)
7
2.3 (s, 3H, CH3), 7.55-8.25 (m, 5H, arom.), 8.10 (s, 1H, CH-
pyridine)
10b
11
13
14
18
19
3050 (CH arom.), 2990, 2980 (CH aliph.)
2.35 (s, 3H, CH3), 7.55-8.25 (m, 12H, 10H arom. + 2H, CH-
pyridine)
3350-3250 (NH2), 3050 (CH arom.), 2990
(CH aliph.), 2200 (CN)
2.40 (s, 3H, CH3), 6.5 (s, 2H, NH2), 7.64-8.24 (m, 10H, arom)
3050 (CH arom.), 2980, 2990 (CH aliph.),
1690 (CO)
2.45 (s, 3H, CH3), 7.55-8.25 (m, 5H, arom.), 8.5 (s, 1H, CH-
pyridine), 9.62 (s, 1H, CHO)
3400 (OH), 3050 (CH arom.), 2990, 2980
(CH aliph.)
2.35 (s, 3H, CH3), 6.9 (s, 1H, CH, aldoxime), 7.60-8.24 (m, 5H,
arom.), 8.47 (s, 1H, CH-pyridine), 11.20 (s, 1H, OH)
2.40 (s, 3H, CH3), 2.52 (s, 6H, 2CH3), 7.55-8.05 (m, 7H, (5H,
arom + 2H, 2CH.))
3050 (CH arom.), 2990 (CH aliph.), 2210
(CN)
3350-3150 (NH2 + NH), 3050 (CH arom.),
2990 (CH aliph.)
2.30 (s, 3H, CH3), 2.48 (s, 6H, 2CH3), 7.5 (s, 1H, CH), 7.1 (s,
1H, CH), 7.5 (s, CH), 7.55-8.05 (m , 5H, arom), 9.5 (s, 2H,
NH2), 10.9 (s, 1H, NH)
20
21
22
3300 (NH), 3040 (CH arom.), 2990, 2980
(CH aliph.)
2.36 (s, 3H, CH3), 2.47 (s, 6H, 2CH3), 6.98-8.05 (m, 12H, (10H,
arom + 2H, 2CH.)), 11.10 (s, 1H, NH)
3060 (CH arom.), 2990, 2980 (CH aliph.),
1690 (CO)
2.40 (s, 3H, CH3), 2.45 (s, 6H, 2CH3), 7.53-8.05 (m, 12H, (10H,
arom + 2H, 2CH.))
3350-3250 (NH2), 3050 (CH arom.), 2990
(CH aliph.), 2210 (CN)
2.35 (s, 3H, CH3), 2.49 (s, 6H, 2CH3), 3.79 (s, 1H, CH-pyran),
5.6 (s, 2H, NH2), 6.53 (s, 1H, CH-pyran), 7.53-8.05 (m, 11H,
(10H, arom + 1H, 1CH))
23
24
3060 (CH arom.), 2990, 2980 (CH aliph.),
2200 (CN)
2.2 (s, 3H, CH3), 2.40 (s, 3H, CH3), 2.55 (s, 3H, CH3), 7.57-8.25
(m, 6H, (5H, arom. + 1H, CH-pyridine))
3290 (NH), 3040 (CH arom.), 2990, 2980
(CH aliph.)
2.01 (s, 3H, CH3), 2.30 (s, 3H, CH3), 2.45 (s, 3H, CH3), 7.53-
8.38 (m, 11H, (10H, arom. + 1H, CH-pyridine)), 11.1 (s, 1H,
NH)
25a
25b
26
3360-3230 (NH2 + NH), 3050 (CH arom.),
2980 (CH aliph.)
2.2 (s, 3H, CH3), 2.35 (s, 3H, CH3), 2.55 (s, 3H, CH3), 7.53-8.38
(m, 6H (5H, arom) + 1H, CH-pyridine), 9.35 (s, 2H, NH2), 11.12
(s, 1H, NH)
3350-3220 (NH2 + NH), 3050 (CH arom.),
2990 (CH aliph.), 1655 (CO)
2.1 (s, 3H, CH3), 2.35 (s, 3H, CH3), 2.50 (s, 3H, CH3), 6.35 (s,
2H, NH2), 7.53-8.38 (m, 6H, (5H, arom. +1H, CH-pyridine),
10.55 (s, 1H, NH)
3050 (CH arom.), 2990, 2980 (CH aliph.),
1690 (CO)
2.40 (s, 3H, CH3), 2.50 (s, 3H, CH3), 6.7 (s, 1H, CH-ethylenic),
7.53-8.28 (m, 12H, (10H, arom. + 1H, CH-ethylenic + 1H, CH,
pyridine))