Synthesis of 5-Cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones

Abstract

Two different approaches to the synthesis of 1-unsubstituted 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones have been developed. The first includes N(1)-protection of the starting 5-acetyl-3,4-dihydropyrimidine-2(1H)-one, further Claisen–Schmidt reaction, and cleavage of the protecting group. The second approach consists of one-pot condensation of urea, aldehyde, and cinnamoylacetone as dicarbonyl component. The 5-cinnamoylderivative synthesis starting from 5-acetyl-1,3-dialkyl-3,4-dihydropyrimidine-2(1H)-ones is also shown.

GRAPHICAL ABSTRACT

Keywords:

• Biginelli reaction
• 3,4-dihydropyrimidin-2(1H)-ones
• methoxymethylation
• one-pot condensation
• protecting group

Notes

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