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Synthesis 2008(11): 1703-1706  
DOI: 10.1055/s-2008-1067015
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-(2-Imino-2,3-dihydropyrido[3,2-e]-1,3-thiazin-(Z)-4-ylidene)acetamide Derivatives

Kazuhiro Kobayashi*, Daisuke Iitsuka, Hisatoshi Konishi
Department of Materials Science, Faculty 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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Publikationsverlauf

Received 11 January 2008
Publikationsdatum:
11. April 2008 (online)

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Abstract

A facile two-step preparation of the title pyridothiazine derivatives starting from commercially available 2-chloro-6-methylpyridine-3-carbonitrile is described. The reaction of this nitrile with magnesium enolates of tertiary acetamides affords (Z)-3-amino-3-(2-chloro-6-methylpyridin-3-yl)propenamide derivatives, which in turn are allowed to react with isothiocyanates in the presence of sodium hydride to give the desired products in satisfactory yields.

Key words

amides - cyclizations - heterocycles - imines - pyridines