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Synthesis 2004(7): 1021-1028  
DOI: 10.1055/s-2004-822325
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Approach to 1,2-Dihydro-2-Oxo-3-Pyridinecarboxylic Ester via Aromatization Induced by Deamidation

Gang Yua, Shaozhong Wanga, Kai Wanga, Yuefei Hu*a,b, Hongwen Hua
a Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
b Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China
Fax: +86(25)83317761; e-Mail: yfh@mail.tsinghua.edu.cn;
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Publication History

Received 24 December 2003
Publication Date:
02 April 2004 (online)

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Abstract

A novel approach was developed for the preparation of 4,6-disubstituted-1,2-dihydro-2-oxo-3-pyridinecarboxylic ester in moderate to good yields. This route involves a reaction sequence of Michael addition, transformation to ene-lactam, and aromatization, featuring easily available material, variable substituents, and good functional compatibility.

Key words

synthesis - ethyl acetamidocyanoacetate - aromatization via deamidation - sodium carbonate - 4,6-disubstituted-1,2-dihydro-2-oxo-3-pyridinecarboxylic ester