1218-57-1Relevant academic research and scientific papers
Formation of γ-oxoacids and 1 H-pyrrol-2(5 H)-ones from α,β-unsaturated ketones and ethyl nitroacetate
Aginagalde, Maialen,Bello, Tamara,Masdeu, Carme,Vara, Yosu,Arrieta, Ana,Cossio, Fernando P.
supporting information; experimental part, p. 7435 - 7438 (2010/12/25)
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.
