Optimization of the four-component reaction of benzil, benzaldehyde, benzylamine and ammonium acetate under various conditionsa.
Entry | Solvent | Catalyst (mol%) | Temp. | Time (min) | Yieldb (%) |
---|---|---|---|---|---|
1 | Ethanol | 0.36 | Reflux | 55 | 69 |
2 | Acetonitrile | 0.36 | Reflux | 55 | 61 |
3 | Water | 0.36 | Reflux | 80 | 78 |
4 | Dichloromethane | 0.36 | Reflux | 70 | 45 |
5 | Chloroform | 0.36 | Reflux | 70 | 49 |
6 | Tetrahydrofuran | 0.36 | Reflux | 70 | 43 |
7 | Solvent-free | 0.36 | 80 °C | 35 | 95 |
8 | Solvent-free | 0.24 | 80 °C | 55 | 79 |
9 | Solvent-free | 0.48 | 80 °C | 35 | 92 |
10 | Solvent-free | 0.36 | 25 °C | 120 | 35 |
11 | Solvent-free | 0.36 | 60 °C | 65 | 69 |
12 | Solvent-free | 0.36 | 70 °C | 45 | 75 |
13 | Solvent-free | 0.36 | 90 °C | 35 | 93 |
14 | Solvent-free | 0.36 | 100 °C | 35 | 91 |
15w | Solvent-free | BF3–SiO2/0.36 | 80 °C | 150 | 68 |
16 | Solvent-free | MgCl2/0.36 | 80 °C | 80 | 56 |
17 | Solvent-free | SbCl5–SiO2/0.36 | 80 °C | 150 | 65 |
Reaction conditions: benzil (1 mmol), benzaldehyde (1 mmol), benzylamine (1 mmol), ammonium acetate (4 mmol), and the required amount of catalyst.
The yields refer to the separated product.