Synthesis of Adamantylated Pyrimidines Using the Biginelli Reaction

Abstract

Using an adamantane 3-oxonitrile and adamantane 1,3-dicarbonyl compounds in the three-component Biginelli reaction promoted by trimethylsilyl chloride, adamantylated pyrimidines are prepared. The reaction with the oxonitrile leads to 6-(1-adamantyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles and/or 2-benzylidene-3-oxonitriles depending on the type of aromatic aldehyde. 1,3-Dicarbonyl adamantane compounds give 1-adamantyl(2-thioxo-1,2,3,4-tetrahydropyrimidine-5-yl)methanones with low yields. An adamantylated 2-thioxo-1,2,3,4-tetrahydropyrimidine is used to prepare thiazolo[3,2-a]pyrimidine derivatives.

Key words

2-thioxo-1,2,3,4-tetrahydropyrimidines - adamantane - 1,3-dicarbonyl compounds - 3-oxonitriles - Biginelli reaction - trimethylsilyl chloride

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