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Synthesis 2003(4): 0487-0490
DOI: 10.1055/s-2003-37642
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Regioselective Tandem Reaction between Chalcones and 2-Acetamido­acetamide Promoted by Cs2CO3 for the Preparation of 3-Unsubstituted 2-Pyridones

Shaozhong Wang, Gang Yu, Jun Lu, Kun Xiao, Yuefei Hu*,, Hongwen Hu
Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
Fax: +86(10)6277114; e-Mail: yfh@mail.tsinghua.edu.cn;
Further Information

Publication History

Received 15 October 2002
Publication Date:
07 March 2003 (online)

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Abstract

A novel procedure was developed for the preparation of 3-unsubstituted 2-pyridones by a tandem reaction between chalcones and 2-acetamidoacetamide. The regioselectivity was affected mainly by base used in the reaction. For the symmetrical chalcones, satisfactory results were obtained when the reaction was catalyzed by sodium hydroxide. In the case of unsymmetrical chalcones, cesium carbonate was used as a base to yield desired products regioselectively.

Key words

3-unsubstituted 2-pyridones - 2-acetamidoacetamide - chalcones - cesium carbonate

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Current Address: Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China