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

Gang Yu; Shaozhong Wang; Kai Wang; Yuefei Hu; Hongwen Hu

doi:10.1055/s-2004-822325

PAPER

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

Gang Yu^a, Shaozhong Wang^a, Kai Wang^a, Yuefei Hu*^a,b, Hongwen Hu^a
^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;

Abstract

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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

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References

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