Cyclic condensations of 2-amino-1,3,4-thiadiazole with 1,3-dicarbonyl compounds

The reactions of 2-amino-1,3,4-thiadiazole with 1,3-dicarbonyl compounds are described. 2,4-Pentanedione gave 2-thiocyanato-4,6-dimethylpyrimidine while diethylmalonate and ethyl acetoacetate yielded 5-hydroxy-7H-1,3,4-thiadiazolo3,2-a]pyrimidin-7-one and 7-methyl-5H-1,3,4-thiadiazolo3,2-a]pyrimidin-5-one, respectively. The structure of the latter compound was confirmed by a synthesis of the alternative isomeric structure (5-methyl-7H-1,3,4-thiadiazolo3,2-a]pyrirnidin-7-one) from 2-amino-1,3,4-thiadiazole and α-bromocrotonic acid.