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Synthesis 2009(3): 375-378
DOI: 10.1055/s-0028-1083307
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
Further Information
Received
25 August 2008
Publication Date:
09 January 2009 (online)
Publication History
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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