Table 1.
Entry | Starting materials | Method | Product | Yield, % | |||
Aldehydes | R1 | Aminopyrazoles | R2 | ||||
1 | 1a | H | 2a | 4-F | A | 4a | 54 |
2 | 1b | 2-CH3O | 2a | 4-F | A | 4b | 75 |
3 | 1c | 3-CH3O | 2a | 4-F | A | 4c | 77 |
4 | 1d | 4-CH3O | 2a | 4-F | A | 4d | 75 |
5 | 1e | 4-Cl | 2a | 4-F | A | 4e | 72 |
6 | 1b | 2-CH3O | 2b | 3-F | A | 4f | 83 |
7 | 1d | 4-CH3O | 2b | 3-F | A | 4g | 64 |
8 | 1e | 4-Cl | 2b | 3-F | A | 4h | 89 |
9 | 1b | 2-CH3O | 2c | 2-CH2CH3 | A | 4i | 82 |
10 | 1d | 4-CH3O | 2c | 2-CH2CH3 | A | 4j | 64 |
11 | 1e | 4-Cl | 2c | 2-CH2CH3 | A | 4k | 66 |
12 | 1b | 2-CH3O | 2d | 4-CH2CH3 | A | 4l | 85 |
13 | 1e | 4-Cl | 2d | 4-CH2CH3 | A | 4m | 53 |
14 | 1f | 4-CO2CH3 | 2a | 4-F | B | 4n | 85 |
15 | 1g | 4-NO2 | 2a | 4-F | B | 4o | 87 |
16 | 1h | 4-CN | 2a | 4-F | B | 4p | 90 |
17 | 1f | 4-CO2CH3 | 2b | 3-F | B | 4q | 88 |
18 | 1g | 4-NO2 | 2b | 3-F | B | 4r | 87 |
19 | 1h | 4-CN | 2b | 3-F | B | 4s | 82 |
20 | 1f | 4-CO2CH3 | 2c | 2-CH2CH3 | B | 4t | 61 |
21 | 1g | 4-NO2 | 2c | 2-CH2CH3 | B | 4u | 79 |
22 | 1h | 4-CN | 2c | 2-CH2CH3 | B | 4v | 83 |