Formation of γ-oxoacids and 1H-pyrrol-2(5H)-ones from α,ß-unsaturated ketones and ethyl nitroacetate.

ABSTRACT

Michael addition of ethyl nitroacetate on α,ß-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal-Knorr conditions is also reported.