Investigation of catalytic behaviour of TMIPOP and its relative intermediates and other known catalysts upon the synthesis of 1aa.
| Entry | Catalyst | Load of catalyst | Yield (%) |
|---|---|---|---|
| 1 | TIPOP | 20 mg | 62 |
| 2 | FeCl3 | 20 mol% | 35 |
| 3 | TMIPOP | 20 mg | 80 |
| 4 | HCl | 20 mol% | Trace |
| 5 | AlCl3 | 20 mol% | 25 |
| 6 | H2SO4 | 20 mol% | 45 |
| 7 | Trityl chloride | 20 mol% | 30 |
| 8 | Trityl bromide | 20 mol% | 42 |
| 9 | Silica sulfuric acid (SSA)63 | 20 mg | 75 |
| 10 | NH2SO3H | 20 mol% | 20 |
| 11 | Fe(HSO4)3 | 20 mol% | 35 |
| 12 | Al(HSO4)3 | 20 mol% | 30 |
| 13 | Ca(HSO4)2 | 20 mol% | 25 |
Reaction conditions: benzaldehyde (1 mmol, 0.106 g), ke3 (1 mmol, 0.370 g), 3-(1H-indol-3-yl)-3-oxopropanenitrile (1 mmol, 0.184 g) and ammonium acetate (1.5 mmol, 0.115 g). Solvent-free, 110 °C, 45 min.