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Table 3 Tandem Aldol-Michael reactions of barbituric acid 1a,b and dimedone 2 with aldehydes 3 in aqueous diethylamine medium a

From: Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives

# 3 R1 R2 yield (%)b
1 4a CH3 Ph 98
2 4b CH3 p-CH3Ph 97
3 4c CH3 p-ClPh 97
4 4d CH3 p-BrPh 95
5 4e CH3 m-BrPh 93
6 4f CH3 p-CH3OPh 92
7 4 g CH3 o-NO2Ph 93
8 4 h CH3 2,4-Cl2Ph 90
9 4i CH3 2,6-Cl2Ph 89
10 4j CH3 2-Naphthaldehyde 94
11 4 k CH3 p-HO-Ph 91
12 4 l H Ph 93
13 4 m H p-CH3Ph 91
14 4n H p-ClPh 90
15 4o H p-BrPh 89
16 4p H 2-Naphthaldehyde 90
  1. aAll reactions were carried out with barbituric acid derivatives 1a,b (1.5 mmol), dimedone 2 (1.5 mmol) aldehydes 3 (1.5 mmol) and diethylamine (1.5 mmol) in water (1.5 mL) for the specified time. bYield of isolated product 4a-p.