Uracil Derivatives and Related Compounds. I. Condensation of Monosubstituted Urea and Ethyl Acetoacetate.

Abstract

All of the compounds derived from the condensation of monosubstituted ureas (substituents : phenyl, cyclohexyl, methyl) and ethyl acetoacetate were 3-substituted 6-methyluracil derivatives. In the case of phenylurea, the hydrolysis of the condensation product gave 1-[3-(3-phenylureido) crotonoyl]-3-phenylurea without the formation of a uracil ring, and when the condensation product was methylated, the ring closure occurred to afford 1, 6-dimethyl-3-phenyluracil. In the case of cyclohexylurea or methylurea, 5-alkyl-6-methyluracil was obtained in a good yield via ethyl 3-(3-alkylureido) crotonate.