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Synthesis 2002(15): 2191-2194
DOI: 10.1055/s-2002-34845
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New β-Keto Amide Synthesis

Yanping Chena, Scott McN. Sieburth*b
a Department of Chemistry, State University of New York at Stony Brook, Stony Brook NY 11794-3400 USA
b Department of Chemistry, Temple University, 1901 N. 13th St., Philadelphia, PA 19010 USA
Fax: +1(215)2041532; e-Mail: sieburth@astro.temple.edu;
Further Information

Publication History

Received 14 June 2002
Publication Date:
21 October 2002 (online)

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Abstract

In a modification of the Wierenga-Skulnick β-ketoester synthesis, the dianions of malonic acid mono-amides were condensed with acid chlorides. Acidic workup led to decarboxylation and isolation of the corresponding β-keto amides in good-to-excellent yields. A similar procedure with cyanoacetic acid gave β-keto nitriles.

Key words

amides - carboxylic acids - condensation - ketones - nitriles

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For a discussion of keto-enol tautomers in β-keto amides see ref. [16]