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

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-ket...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-11, Vol.75 (21), p.7435-7438
Main Authors: Aginagalde, Maialen, Bello, Tamara, Masdeu, Carme, Vara, Yosu, Arrieta, Ana, Cossío, Fernando P
Format: Article
Language:English
Subjects:
Acetates - chemistry
Acids - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Ketones - chemistry
Models, Molecular
Molecular Conformation
Nitro Compounds - chemistry
Organic chemistry
Oxygen - chemistry
Preparations and properties
Pyrroles - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101388x