Studies on Ketene and Its Derivatives. XVII. Reaction of Diketene with Imidates.

Abstract

Reactions of diketene with iminothers such as benziminoethylether and phenacetiminoethylether were investigated. Refluxing of benziminoethylether with diketene in ether afforded 2-ethoxy-6-methyl-2-phenyl-3, 4-dihydro-2H-1, 3-oxazin-4-one (I) and 6-methyl-2-phenyl-4H-1, 3-oxazin-4-one (II). Phenacetiminoethylether reacted with diketene to give 2-benzyl-2-ethoxy-6-methyl-3, 4-dihydro-2H-1, 3-oxazin-4-one (IV), 3-acetyl-2, 6-dibenzyl-4-hydroxypyrimidine (V) and N-acetoacetyl-α-phenylacetamide (VI). The structure assignments of these compounds were described.