Tandem imines formation via auto-hydrogen transfer from alcohols to nitro compounds catalyzed by Cu-isatin Schiff base-γ Fe2O3.
| |||||
|---|---|---|---|---|---|
| Entrya | R1 | R2 | Product | Time (h) | Yield (%) |
| 1 | C6H5 | C6H5 | a | 10 | 92 |
| 2 | C6H5 | 4-OH–C6H4 | b | 8 | 90 |
| 3 | C6H5 | 4-OMe–C6H4 | c | 8 | 84 |
| 4 | C6H5 | 4-Me–C6H4 | d | 9 | 87 |
| 5 | C6H5 | 4-Cl–C6H4 | e | 12 | 71 |
| 6 | 4-Me–C6H4 | C6H5 | f | 13 | 91 |
| 7 | 4-Me–C6H4 | 4-Cl–C6H4 | g | 12 | 68 |
| 8 | 4-Me–C6H4 | 4-OMe–C6H4 | h | 10 | 85 |
| 9 | 4-Me–C6H4 | 4-Me–C6H4 | i | 12 | 83 |
| 10 | 4-OMe–C6H4 | C6H5 | j | 12 | 75 |
| 11 | 4-OMe–C6H4 | 4-Cl–C6H4 | k | 13 | 72 |
| 12 | 4-OMe–C6H4 | 4-OMe–C6H4 | l | 11 | 84 |
| 13 | 4-OMe–C6H4 | 4-Me–C6H4 | m | 14 | 70 |
| 14 | C6H5 | CH3–CH2– | n | 10 | 72 |
| 15 | CH3–CH3–CH2– | C6H5 | o | 12 | 85 |
Reaction conditions: nitro compound (1 mmol), alcohol (1 mmol), KOH (1 mmol), solvent-free, catalyst (1 mol%), 100 °C. Melting points of the solid products were compared with the reported ones in the ESI (Table S1).