Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2001(5): 0731-0734
DOI: 10.1055/s-2001-12760
DOI: 10.1055/s-2001-12760
PAPER
© Georg Thieme Verlag Stuttgart · New York
Preparation of 1,3-Selenazol-4-one Derivatives from Primary Selenoamides and Haloacyl Halides
Further Information
Received
8 December 2000
Publication Date:
15 October 2004 (online)
Publication History
Publication Date:
15 October 2004 (online)
![](https://www.thieme-connect.de/media/synthesis/200105/lookinside/thumbnails/10.1055-s-2001-12760-1.jpg)
Abstract
1,3-Selenazol-4-one derivatives were synthesized by the reaction of primary selenoamides with haloacyl halides in the presence of pyridine.
Key words
primary selenoamide - haloacyl halide - pyridine - 1,3-selenazol-4-one - heterocycles
-
1a
Katritzky AR.Rees CW.Scriven EFV. Comprehensive Heterocyclic Chemistry II Pergamon; London: 1996. p.1-11 -
1b
Back TG. Organoselenium Chemistry: A Practical Approach Oxford University Press; London: 1999. -
1c
Wirth T. Organoselenium Chemistry: Modern Developments in Organic Synthesis Springer; Berlin: 2000. -
2a
Kumar Y.Green R.Borysko KZ.Wise DS.Wotring LL.Townsend LB. J. Med. Chem. 1993, 36: 3843 -
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 -
3a
Cohen VI. Synthesis 1978, 769 -
3b
Cohen VI. Synthesis 1979, 66 -
3c
Shafiee A.Mazloumi A.Cohen VI. J. Heterocycl. Chem. 1979, 16: 1563 -
3d
Sekiguchi M.Ogawa A.Fujiwara S.Kambe N.Sonoda N. Chem. Lett. 1990, 913 -
3e
Shimada K.Matsuda Y.Hikage S.Takeishi Y.Takikawa Y. Bull. Chem. Soc. Jpn. 1991, 64: 1037 -
3f
Dubreuil D.Pradère JP.Giraudeau N.Goli M.Tonnard F. Tetrahedron Lett. 1995, 36: 237 -
3g
Koketsu M.Senda T.Yoshimura K.Ishihara H. J. Chem. Soc., Perkin Trans. 1 1999, 453 -
3h
Koketsu M.Hiramatsu S.Ishihara H. Chem. Lett. 1999, 485 - 5 The reaction of thioamide with β-haloacyl halide yielded 1,3-thiazin-4-one, see:
Okawara T.Kashimura H.Furukawa M. Chem. Pharm. Bull. 1985, 33: 3479 - 6
Ishihara H.Yoshimura K.Koketsu M. Chem. Lett. 1998, 1287
References
Reactions of 1a and 2a at -20 °C, 0 °C, r. t. and reflux gave 3a in 69, 80, 77 and 74% yields, respectively.