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. 2022 Mar 21;12(14):8804–8814. doi: 10.1039/d2ra00451h

Optimizing of the reaction conditions for the synthesis of 1aa.

graphic file with name d2ra00451h-u1.jpg
Entry Solvent Temperature (°C) Catalyst loading (mg) Time (min.) Yieldb (%)
1 120 20 20 80
2 c 110 20 20 80
3 110 30 20 78
4 110 10 20 67
5 110 20 Trace
6 110 120 45
7 100 20 30 50
8 90 20 60 40
9 80 20 60 Trace
11 H2O Reflux 20 240
12 EtOH Reflux 20 240
13 n-Hexane Reflux 20 240 Trace
14 EtOAc Reflux 20 240 35
15 CH2Cl2 Reflux 20 240 20
16 THF Reflux 20 240 45
a

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).

b

Related to isolated yields.

c

Optimal data.