Formation of γ-Oxoacids and 1H-Pyrrol-2(5H)-ones from α,β-Unsaturated Ketones and Ethyl Nitroacetate.

Formation of γ-Oxoacids and 1H-Pyrrol-2(5H)-ones from α,β-Unsaturated Ketones and Ethyl Nitroacetate. Journal of Organic Chemistry 2010, vol 75, pp 7435-7438.

http://pubs.acs.org/doi/abs/10.1021/jo101388x

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.