Heterocyclic syntheses with malonyl chloride. Part 14. A direct synthesis of 4,6-dichloropyrimidines with 5-benzyl or -phenyl and 2-thioalkyl or -thiophenyl substituents

Abstract

4,6-Dichloropyrimidines are formed direct from benzyl- and phenyl-malonyl chlorides with a variety of organic thiocyanates. Attempted extension to reaction of bromomalonyl chloride with thiocyanates yielded 2-alkylthio-8-bromo-7-chloropyrano[3,4-e][1,3]oxazine-4,5-diones.

Possible mechanisms for the two syntheses are discussed.