Substrate scope of the synthesis of multi-substituted pyrazolesa.
| |||
|---|---|---|---|
| Entry | 1 (R1, R2) | 2 (Ar) | Product, yieldb |
| 1 | Ph, Ph | 4-BrC6H4 | 3a, 54%; 4a, 29% |
| 2 | Ph, Ph | 4-ClC6H4 | 3b, 59%; 4b, 28% |
| 3 | Ph, Ph | 4-OMeC6H4 | 3c, 48%; 4c, 27% |
| 4 | 3-FC6H4, Ph | 4-BrC6H4 | 3d, 57%; 4d, 24% |
| 5 | 3-FC6H4, Ph | 4-ClC6H4 | 3e, 59%; 4e, 22% |
| 6 | 3-FC6H4, Ph | 4-OMeC6H4 | 3f, 50%; 4f, 25% |
| 7 | 4-FC6H4, Ph | 4-ClC6H4 | 3g, 55%; 4g, 27% |
| 8 | 4-FC6H4, Ph | 4-BrC6H4 | 3h, 50%; 4h, 27% |
| 9 | 3-ClC6H4, Ph | 4-ClC6H4 | 3i, 54%; 4i, 27% |
| 10 | 3-ClC6H4, Ph | 4-BrC6H4 | 3j, 44%; 4j, 29% |
| 11 | 3-ClC6H4, 4-OMeC6H4 | 4-OMeC6H4 | 3k, 52%; 4k, 29% |
| 12 | 2-BrC6H4, 4-OMeC6H4 | 4-ClC6H4 | 3l, 48%; 4l, 47% |
| 13 | 2-Np, 4-OMeC6H4 | 4-ClC6H4 | 3m, 56%; 4m, 30% |
| 14 | 2-Np, 4-OMeC6H4 | 4-OMeC6H4 | 3n, 54%; 4n, 32% |
| 15 | 2-Np, Ph | 4-ClC6H4 | 3o, 54%; 4o, 31% |
| 16 | 3-FC6H4, 2,4,6-triMeC6H2 | 4-ClC6H4 | 3p, 67%; 4p, 29% |
| 17 | 4-FC6H4, 2,4,6-triMeC6H2 | 4-ClC6H4 | 3q, 65%; 4q, 30% |
| 18 | 4-FC6H4, 2,4,6-triMeC6H2 | 4-OMeC6H4 | 3r, 60%; 4r, 28% |
| 19 | 2-Thiophenyl, Ph | 4-ClC6H4 | 3s, 59%; 4s, 21% |
| 20 | Ph, Ph | 4-NO2C6H4 | 3t, 52%; 4t, 24% |
| 21 | Ph, 3-CF3C6H4 | 4-NO2C6H4 | 3u, 45%; 4u, 29% |
The reaction of 1 (0.2 mmol) with 2 (0.24 mmol) was carried out in the presence of K2CO3 (0.5 mmol) in EtOH (2.5 mL) at room temperature for 12 h.
Isolated yield.