Issue 0, 1971
From the journal:

Journal of the Chemical Society C: Organic

Enamine chemistry. Part XIII. Reaction of αβ-unsaturated acid chlorides with primary and secondary enamines. Synthesis of tetrahydro-2-oxopyridines and octahydro-2-oxoquinolines

P. W. Hickmott  and  G. Sheppard  

Abstract

αβ-Unsaturated acid chlorides react with primary and secondary enamines, obtained by condensation of ammonia or primary amines with β-diketones or β-keto-esters, to give tetrahydro-2-oxopyridines or octahydro-2-oxoquinolines. The evidence available from this and previous work suggests that the reaction involves initial O- or N-acylation followed by a [3,3] sigmatropic rearrangement and cyclisation of the keten intermediate formed on to the nitrogen atom.

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Article information

DOI
https://doi.org/10.1039/J39710002112
Article type
Paper

J. Chem. Soc. C, 1971, 2112-2115

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Enamine chemistry. Part XIII. Reaction of αβ-unsaturated acid chlorides with primary and secondary enamines. Synthesis of tetrahydro-2-oxopyridines and octahydro-2-oxoquinolines

P. W. Hickmott and G. Sheppard, J. Chem. Soc. C, 1971, 2112 DOI: 10.1039/J39710002112

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