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J Org Chem. 2010 Nov 5;75(21):7435-8. doi: 10.1021/jo101388x.

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

Author information

1
Kimika Fakultatea, Kimika Organikoa I Saila, Universidad del País Vasco-Euskal Herriko Uniberstitatea, Manuel de Lardizabal Etorbidea 3, 20018 San Sebastián-Donostia, Spain.

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.

PMID:
20886821
DOI:
10.1021/jo101388x
[Indexed for MEDLINE]

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