Journal of Organic Chemistry 2010-11-05

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

Maialen Aginagalde, Tamara Bello, Carme Masdeu, Yosu Vara, Ana Arrieta, Fernando P Cossío

Index: J. Org. Chem. 75(21) , 7435-8, (2010)

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Abstract

Michael addition of ethyl nitroacetate on α,β-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.