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. 2019 May 21;9(28):15966–15975. doi: 10.1039/c9ra02325a

Optimization of the four-component reaction of benzil, benzaldehyde, benzylamine and ammonium acetate under various conditionsa.

graphic file with name c9ra02325a-u3.jpg
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
a

Reaction conditions: benzil (1 mmol), benzaldehyde (1 mmol), benzylamine (1 mmol), ammonium acetate (4 mmol), and the required amount of catalyst.

b

The yields refer to the separated product.