134
H.M. Faidallah et al. / Journal of Fluorine Chemistry 132 (2011) 131–137
Table 2
1H NMRa spectral data (
d) of pyrazole derivatives.
Compd.
R
R0
ArH and NH (m)
Others
2a
2b
3a
6.70–8.12 (7H)
6.64–8.02 (10H)
6.62–8.20 (6H)
6.53–8.14 (9H)
7.12–8.38 (6H)
7.00–8.10 (11H)
6.98–7.99 (10H)
6.78–8.17 (9H)
7.02–8.04 (13H)
7.11–8.12 (15H)
6.85–7.97 (9H)
7.02–8.03 (8H)
6.92–8.12 (7H)
6.87–8.02 (12H)
6.92–7.89 (10H)
6.89–8.01 (10H)
6.99–8.01 (13H)
7.00–8.14 (13H)
7.12–8.05 (13H)
7.02–7.98 (9H)
7.01–8.08 (7H)
7.00–7.98 (12H)
7.10–8.05 (10H)
7.05–8.11 (10H)
6.82–8.02 (13H)
6.79–8.13 (13H)
6.88–8.02 (12H)
6.92–8.10 (12H)
6.89–8.00 (13H)
6.92–8.01 (10H)
6.82–8.12 (13H)
6.80–8.09 (13H)
6.89–8.05 (9H)
6.90–8.12 (16H)
7.09–8.19 (16H)
7.00–8.01 (19H)
6.82–8.12 (15H)
6.92–8.07 (13H)
6.84–8.11 (14H)
6.62–8.13 (19H)
6.67–8.09 (18H)
3.35 (s, 3H, CH3)
Furyl
CH3
3.38 (s, 3H, CH3)
3b
4a
Furyl
CH3
Cyclohexyl
Ph
3.32 (s, 3H, CH3); 8.65 (s, 1H, NH)
4b
4d
4e
CH3
3.40 (s, 3H, CH3); 8.56 (s, 1H, NH)
CH3
p-Cl C6H4
Cyclohexyl
Ph
3.29 (s, 3H, CH3); 8.75 (s, 1H, NH)
Furyl
Furyl
Furyl
CH3
0.92–1.85 (m, 11H, cyclohexyl); 8.55 (s, 1H, NH)
8.60 (s, 1H, NH); 8.75 (s, 1H, NH)
4f
4g
Naphthyl
Ph
8.78 (s, 1H, NH); 9.01 (s, 1H, NH)
5a
3.32 (s, 3H, CH3); 8.56 (s, 1H, NH); 8.78 (s, 1H, NH)
3.28 (s, 3H, CH3); 8.62 (s, 1H, NH); 8.81 (s, 1H, NH)
0.88–1.76 (m, 11H, cyclohexyl); 8.58 & 8.82 (2s, 1H, NH)
8.59 (s, 1H, NH); 8.80 (s, 1H, NH)
5b
5c
CH3
p-Cl C6H4
Cyclohexyl
Ph
Furyl
Furyl
CH3
5d
6a
Ph
3.35 (s, 3H, CH3); 8.45 (s, 1H, NH); 8.70 (s, 1H, NH)
3.29 (s, 3H, CH3); 8.56 (s, 1H, NH); 8.78 (s, 1H, NH)
8.55 (s, 1H, NH); 8.80 (s, 1H, NH)
6b
6c
CH3
Benzyl
Ph
Furyl
Furyl
Furyl
CH3
6d
6e
Benzyl
Benzoyl
Ph
4.52 (d, 2H, CH2); 8.62 (s, 1H, NH); 8.85 (s, 1H, NH)
8.49 (s, 1H, NH); 8.72 (s, 1H, NH)
7a
3.30 (s, 3H, CH3); 8.52 (s, 1H, NH); 8.68 (s, 1H, NH)
0.95–1.82 (m, 11H, cyclohexyl); 8.60 & 8.75 (2s, 1H, NH)
8.60 (s, 1H, NH); 8.90 (s, 1H, NH)
7c
Furyl
Furyl
CH3
Cyclohexyl
Ph
7d
8a
Ph
3.32 (s, 3H, CH3); 3.85 (s, 2H, CH2); 4.42 (s, 2H, CH2)
3.30 (s, 3H, CH3); 3.80 (s, 2H, CH2); 4.51 (s, 2H, CH2)
3.90 (s, 2H, CH2); 4.52 (s, 2H, CH2)
8b
8c
CH3
Benzyl
Ph
Furyl
Furyl
CH3
8e
Benzoyl
Ph
3.84 (s, 2H, CH2); 4.46 (s, 2H, CH2)
9a
3.29 (s, 3H, CH3); 3.87 (s, 2H, CH2); 4.50 (s, 2H, CH2)
3.79 (s, 2H, CH2); 4.48 (s, 2H, CH2)
9b
10a
11a
11b
11c
12a
13a
13b
13d
14a
15
Furyl
Furyl
CH3
Ph
Ph
3.52–4.12 (m, 4H, 2CH2)
Ph
3.30 (s, 3H, CH3); 3.72 (s, 2H, CH2); 4.02 (s, 2H, CH2)
3.84 (s, 2H, CH2); 4.15 (s, 2H, CH2)
Furyl
Furyl
CH3
Ph
Benzyl
Ph
3.75 (s, 2H, CH2); 4.09 (s, 2H, CH2)
3.32 (s, 3H, CH3); 3.78 (s, 2H, CH2); 4.08 (s, 2H, CH2)
3.30 (s, 3H, CH3); 4.35 (s, 2H, CH2)
CH3
Ph
CH3
Benzyl
Benzyl
Ph
3.29 (s, 3H, CH3); 4.38 (s, 2H, CH2)
Furyl
CH3
4.42 (s, 2H, CH2)
3.35 (s, 3H, CH3)
Furyl
Furyl
Furyl
CH3
3.75 (s, 2H, CH2)
16
3.62 (s, 3H, CH3)
17
4.50 (d, 1H, CH); 5.20 (m, 1H, CH)
18
4.42 (d, 1H, CH); 3.80 (m, 1H, CH)
a
Solutions in a mixture of CDCl3 and DMSO-d6,
d in ppm.
Table 3
13C NMRa spectral data (
d
) of pyrazole derivative.
Compd.
R
R0
Ar and pyrazole C
CH3
Other C
2a
2b
CH3
148.9, 141.2, 138.7, 126.2, 124.1, 122.4, 114.5
147.8, 140.9, 142.6, 139.5, 128.1, 127.2, 124.2,
123.2, 121.1, 112.5, 109.3
14.6
Furyl
3a
4a
CH3
CH3
146.7, 140.4, 136.5, 127.8, 125.5, 121.4, 110.3
145.0, 142.3, 137.8, 128.2, 125.3, 120.2, 112.6
14.8
14.5
Cyclohexyl
176.2 (CO); 23.0, 29.1,
34.5, 49.6 (cyclohexyl)
175.0 (CO)
4b
4f
CH3
Ph
Ph
146.0, 141.2, 138.6, 129.3, 128.4, 127.9, 126.4,
14.3
125.1, 123.5, 122.1, 110.3
Furyl
146.3, 144.5, 142.6, 140.3, 138.2, 129.5, 128.4,
178.0 (CO)
128.2, 127.4, 125.1, 123.0, 122.6, 120.1, 113.5, 108.6
149.0, 143.4, 140.6, 137.2, 129.0, 128.3, 128.1, 127.5, 126.3, 120.6, 109.2
147.0, 145.6, 143.2, 141.3, 139.6, 129.4, 128.2,
5a
5d
CH3
Ph
Ph
14.2
14.6
14.6
177.4 (CO)
176.5 (CO)
Furyl
128.0, 127.3, 126.2, 122.6, 121.0, 112.6, 110.4
6b
7c
CH3
Benzyl
146.4, 142.3, 140.0, 136.9, 129.2, 128.4, 128.0, 127.6, 125.6, 122.4, 110.3
147.7, 143.2, 141.0, 138.9, 128.6, 127.6, 124.2, 123.0, 122.6, 112.5, 108.6
204 (CS); 63.2 (CH2)
201 (CS); 22.9, 28.8,
34.2, 48.6 (cyclohexyl)
192 (CO); 38.6 (CH2)
Furyl
Cyclohexyl
8a
8c
CH3
Ph
Ph
146.2, 142.8, 140.4, 137.6, 134.2, 129.5, 128.3, 128.2, 127.8, 125.3,
121.8, 109.2
Furyl
147.6, 142.9, 140.5, 139.2, 134.0, 133.2, 129.4,
194 (CO); 39.2 (CH2)
128.6, 128.3, 127.5, 126.4, 123.6, 122.6, 121.4, 113.5, 106.5
146.8, 143.6, 141.2, 138.6, 135.4, 133.3, 129.8, 128.2, 128.0, 127.6, 125.0, 116.5
149.2, 147.6, 146.4, 142.2, 140.6, 139.8, 138.7, 136.5, 134.2, 133.6, 129.8, 128.3,
128.2, 127.6, 126.4, 124.2, 122.3, 116.6
11a
14a
CH3
CH3
Ph
Ph
14.2
14.2
189 (CO); 38.8, 36.4 (CH2)
15
Furyl
148.9, 147.2, 145.4, 142.3, 140.6, 138.8, 136.4,
39.5 (CH2)
134.0, 130.5, 129.8, 128.4, 128.3, 126.9, 125.4, 123.8, 122.4, 120.5, 108.2
a
Solutions in a mixture of CDCl3 and DMSO-d6,
d in ppm.