Regioselective Synthesis of 2(1H)-Pyridinones from β-Aminoenones and Malononitrile. Reaction Mechanism

The identification of some intermediates of the reactions between β-aminoenones and malononitrile to give 2(1H)-pyridinones has allowed us to obtain valuable information concerning its mechanism. These reactions begin with a conjugated addition of the nitrile to the enone followed by elimination. Th...

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Bibliographic Details
Published in:Journal of organic chemistry 1999-12, Vol.64 (26), p.9493-9498
Main Authors: Alberola, Angel, Calvo, Luis A, Ortega, Alfonso González, Sañudo Ruíz, M. Carmen, Yustos, Pedro, Granda, Santiago García, García-Rodriguez, Esther
Format: Article
Language:English
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Summary:The identification of some intermediates of the reactions between β-aminoenones and malononitrile to give 2(1H)-pyridinones has allowed us to obtain valuable information concerning its mechanism. These reactions begin with a conjugated addition of the nitrile to the enone followed by elimination. The compounds thus obtained cyclize to nonisolable 2H-pyran-2-imine. This afforded 2(1H)-pyridinones by ring opening to unsaturated aminoamides followed by cyclization (Dimroth-type rearrangement).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991121o