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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

    References

  • 1a Sherlock MH. Kaminski JJ. Tom WC. Lee JF. Wong SC. Kreutner W. Bryant RW. McPhail AT. J. Med. Chem.  1988,  31:  2108 
    Google Scholar
  • 1b Delieza V. Detsi A. Bardakos V. Igglessi-Markopoulou O. J. Chem. Soc., Perkin Trans. 1  1997,  1487 
    Google Scholar
  • 1c Mitsos C. Zografos A. Igglessi-Markopoulou O. J. Org. Chem.  2003,  68:  4567 
    Google Scholar
  • 2a Santilli AA. Scotese AC. Bauer RF. Bell SC. J. Med. Chem.  1987,  30:  2270 
    Google Scholar
  • 2b Kuroda T. Suzuki F. Tamura T. Ohmori K. Hosoe H. J. Med. Chem.  1992,  35:  1130 
    Google Scholar
  • 2c Pratt JK. Donner P. McDaniel KF. Maring CJ. Kati WM. Mo H. Middleton T. Liu Y. Ng T. Xie Q. Zhang R. Montgomery D. Molla A. Kempf DJ. Kohlbrenner W. Bioorg. Med. Chem. Lett.  2005,  15:  1577 
    Google Scholar
  • 3 Kobayashi K. Iitsuka D. Konishi H. Synthesis  2007,  51 
    Article in Thieme ConnectGoogle Scholar
  • 4 Penhoat M. Levacher V. Dupas G. J. Org. Chem.  2003,  68:  9517 
    CrossrefPubMedGoogle Scholar