Facile Preparation of 1,3-Selenazole-5-carboxylic Acids and the Carboxylates by Reaction of Selenazadienes with Chloroacetyl Chloride

Abstract

Reaction of selenazadienes with chloroacetyl chloride gave 1,3-selenazole-5-carboxylic acids or 1,3-selenazole-5-carboxy­lates.

Key words

selenazadienes - chloroacetyl chloride - 1,3-selenazoles - heterocycles

References

• 1a Comprehensive Heterocyclic Chemistry II   Vol. 1-11:  Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996. 
• 1b Back TG. Organoselenium Chemistry: A Practical Approach   Oxford University Press; Oxford: 1999. 
• 1c Wirth T. Organoselenium Chemistry. Modern Developments in Organic Synthesis   Springer; Berlin: 2000. 
• 1d Ishihara H. Koketsu M. Fukuta Y. Nada F. J. Am. Chem. Soc.  2001,  123:  8408 
• 2a Koketsu M. Ishihara H. Hatsu M. Res. Commun. Mol. Pathol. Pharmacol.  1998,  101:  179 
• 2b Koketsu M. Ishihara H. Wu W. Murakami K. Saiki I. Eur. J. Pharm. Sci.  1999,  9:  157 
• 2c Wu W. Murakami K. Koketsu M. Yamada Y. Saiki I. Anticancer Res.  1999,  19:  5375 
• 2d Cho SI. Koketsu M. Ishihara H. Matsushita M. Nairn AC. Fukazawa H. Uehara Y. Biochim. Biophys. Acta  2000,  1475:  207 
• 2e Koketsu M. Choi SY. Ishihara H. Lim BO. Kim H. Kim SY. Chem. Pharm. Bull.  2002,  50:  1594 
• 2f Gutzkow KB. Låhne HU. Naderi S. Torgersen KM. Skaalhegg B. Koketsu M. Uehara Y. Blomhoff HK. Cell. Signal.  2003,  15:  871 
• 3a Segi M. Takahashi M. Nakajima T. Suga S. Murai S. Sonoda N. Tetrahedron Lett.  1988,  29:  6965 
• 3b Li GM. Niu S. Segi M. Zingaro RA. Yamamoto H. Watanabe K. Nakajima T. Hall MB. J. Org. Chem.  1999,  64:  1565 
• 4a Dubreuil D. Pradère JP. Giraudeau N. Goli M. Tonnard F. Tetrahedron Lett.  1995,  36:  237 
• 4b Purseigle F. Dubreuil D. Marchand A. Pradère JP. Goli M. Toupet L. Tetrahedron  1998,  54:  2545 
• 6 Koketsu M. Nada F. Mio T. Ishihara H. Heterocycles  2003,  60:  1211 
• 8a Tables of Interatomic Distances and Configuration in Molecules and Ions   The Chemical Society; London: 1958. 
• 8b Tables of Interatomic Distances and Configuration in Molecules and Ions   The Chemical Society; London: 1965. 
• 8c Li GM. Zingaro RA. Segi M. Reibenspies JH. Nakajima T. Organometallics  1997,  16:  756 
• 9 Noack A. Hartmann H. Tetrahedron  2002,  58:  2137 

5

This work was first reported at the 10th Blue Danube Symposium on Heterocyclic Chemistry, Vienna, Austria, September 3-6, 2003.

7

Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication, CCDC No. 220759 for 3d. Copies of this information can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: [phone] or e-mail: [e-mail]).