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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.
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BMC Chemistry

ISSN: 2661-801X

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