Cyclization of arylhydrazone 3a to indazoles 4a and 5a.
| |||||
|---|---|---|---|---|---|
| Entry | Reagent | Solvent | Temp., time | Product | Yield |
| 1 | 5 equiv. TFA | DCM | 25 °C, 12 h | 4a | 63% |
| 2 | 5 equiv. TFA | MeCN | 25 °C, 12 h | 4a | 64% |
| 3 | AcOH | Neat | r. t., 12 h | 4a | 0% |
| 4 | 30 equiv. AcOH | MeCN | 70 °C, 12 h | 4a | 56% |
| 5 | 30 equiv HCOOH | MeCN | r. t., 12 h | 4a | 56% |
| 6 | 3 equiv. K2CO3 | MeOH | 70 °C, 1 h | 5a | 67% |
| 7 | 3 equiv. K2CO3 | MeOH | 25 °C, 12 h | 5a | 67% |
| 8 | 4 equiv. KOH | EtOH | r. t., 12 h | 5a | 59% |