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
