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Synthesis 2009(3): 375-378  
DOI: 10.1055/s-0028-1083307
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Synthesis of 4-Hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide Derivatives

Kazuhiro Kobayashi*, Daisuke Iitsuka, Shuhei Fukamachi, Hisatoshi Konishi
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 25 August 2008
Publication Date:
09 January 2009 (online)

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Abstract

A simple method for synthesizing 1-aryl-4-hydroxy-N,N-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamides has been developed. Thus, 3-(2-chloropyridin-3-yl)-N,N-di­methyl-3-oxopropanamide, easily prepared by treating ethyl 2-chloropyridine-3-carboxylate with lithium enolate of N,N-dimeth­ylacetamide, smoothly reacts with a range of aryl isocyanates in the presence of two molar amounts of sodium hydride to provide the desired products in moderate yields.

Key words

carbanions - fused-ring system - isocyanates - naphthyridines - tandem reaction

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