Studies on Ketene and Its Derivatives. XLI. Reaction of α-Aminoketone with Diketene

Abstract
The reaction of diketene with α-aminoketone derivatives was studied. Ethyl α-aminoacetoacetate (IIIa) and 3-aminoacetylacetone (IIIb) react with diketene to give 3-acetyl-5-carbethoxy-2-hydroxypyrrole (IVa) and 3, 5-diacetyl-2-hydroxy-4-methylpyrrole (IVb), respectively. α-Aminoacetone (IIIc) and phenacylamine (IIId) afford N-acetonylaceto-acetamide (Ic) and N-phenacylacetoacetamide (Id). On treatment with dilute alkali, Ic and Id are transformed to 3-acetyl-4-methyl-3-pyrrolin-2-one (IVc) and 3-acetyl-4-phenyl-3-pyrrolin-2-one (IVd), respectively.

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