Synthesis 2006(16): 2738-2742  
DOI: 10.1055/s-2006-942494
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-Selenoxoperhydro-1,3-selenazin-4-ones and 2-Selenoxo-1,3-selenazolidin-4-ones via Diselenocarbamate Intermediates

Mamoru Koketsu*a, Yusuke Yamamurab, Hideharu Ishihara*b
a Division of Instrumental Analysis, Life Science Research Center, Gifu University, Gifu 501-1193, Japan
b Department of Chemistry, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan
Fax: +81(58)2301893; e-Mail: koketsu@cc.gifu-u.ac.jp;
Further Information

Publication History

Received 27 March 2006
Publication Date:
13 July 2006 (eFirst)

Abstract

The treatment of substituted acryloyl isoselenocyanates with sodium hydroselenide gave 2-selenoxoperhydro-1,3-selenazin-4-ones. The reaction of diselenocarbamates, generated from alkyl isoselenocyanates and sodium hydroselenide, with bromo­acetyl bromide afforded 2-selenoxo-1,3-selenazolidin-4-ones.

    References

  • 1a Comprehensive Heterocyclic Chemistry II   Vols. 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 Organoselenium Chemistry. Modern Developments in Organic Synthesis, In Topics in Current Chemistry   Vol. 208:  Wirth T. Springer; Heidelberg: 2000. 
  • 1d Murai T. Kato S. Top. Curr. Chem.  2000,  208:  177 
  • 1e Ishihara H. Koketsu M. Fukuta Y. Nada F. J. Am. Chem. Soc.  2001,  123:  8408 
  • 2a Koketsu M. Ishihara H. Wu W. Murakami K. Saiki I. Eur. J. Pharm. Sci.  1999,  9:  157 
  • 2b Wu W. Murakami K. Koketsu M. Yamada Y. Saiki I. Anticancer Res.  1999,  19:  5375 
  • 2c Cho SI. Koketsu M. Ishihara H. Matsushita M. Nairn AC. Fukazawa H. Uehara Y. Biochim. Biophys. Acta  2000,  1475:  207 
  • 2d Koketsu M. Choi SY. Ishihara H. Lim BO. Kim H. Kim SY. Chem. Pharm. Bull.  2002,  50:  1594 
  • 2e Gutzkow KB. Låhne HU. Naderi S. Torgersen KM. Skålhegg B. Koketsu M. Uehara Y. Blomhoff HK. Cell. Signal.  2003,  15:  871 
  • 3 Park Y.-J. Koketsu M. Kim JM. Yeo J.-H. Ishihara H. Lee K.-G. Kim SY. Kim C.-K. Biol. Pharm. Bull.  2003,  26:  1657 
  • 4a Koketsu M. Takenaka Y. Ishihara H. Synthesis  2001,  731 
  • 4b Zhang P.-F. Chen Z.-C. Synthesis  2000,  1219 
  • 4c Koketsu M. Senda T. Yoshimura K. Ishihara H. J. Chem. Soc., Perkin Trans. 1  1999,  453 
  • 4d Lai LL. Reid DH. Synthesis  1993,  870 
  • 4e Moriarty RM. Vaid BK. Duncan MP. Levy SG. Prakash O. Goyal S. Synthesis  1992,  845 
  • 4f Shimada K. Matsuda Y. Hikage S. Takeishi Y. Takikawa Y. Bull. Chem. Soc. Jpn.  1991,  64:  1037 
  • 4g Shafiee A. Shafaati A. Habibi-Khameneh B. J. Heterocycl. Chem.  1989,  26:  709 
  • 4h Cohen VI. Synthesis  1979,  66 
  • 4i Potts KT. Huang F. Khattak RK. J. Org. Chem.  1977,  42:  1644 
  • 4j Cava MP. Saris LE. J. Chem. Soc., Chem. Commun.  1975,  617 
  • 5a Sommen GL. Linden A. Heimgartner H. Eur. J. Org. Chem.  2005,  3128 
  • 5b Atanassov PK. Linden A. Heimgartner H. Helv. Chim. Acta  2004,  87:  1452 
  • 5c Atanassov PK. Linden A. Heimgartner H. Helv. Chim. Acta  2003,  86:  3235 
  • 5d Billert T. Beckert R. Doring M. Gorls H. J. Prakt. Chem.  1999,  341:  332 
  • 5e Banert K. Toth C. Angew. Chem., Int. Ed. Engl.  1995,  34:  1627 
  • 6a Sommen GL. Linden A. Heimgartner H. Heterocycles  2005,  65:  1903 
  • 6b Zhou Y. Heimgartner H. Helv. Chim. Acta  2000,  83:  539 
  • 6c Kanda T. Aoki H. Mizoguchi K. Shiraishi S. Murai T. Kato S. Organometallics  1996,  15:  5753 
  • 7a Koketsu M. Fukuta Y. Ishihara H. J. Org. Chem.  2002,  67:  1008 
  • 7b Koketsu M. Ishida M. Takakura N. Ishihara H. J. Org. Chem.  2002,  67:  486 
  • 7c Koketsu M. Nada F. Hiramatsu S. Ishihara H. J. Chem. Soc., Perkin Trans. 1  2002,  737 
  • 7d Koketsu M. Fukuta Y. Ishihara H. Tetrahedron Lett.  2001,  42:  6333 
  • 7e Ishihara H. Koketsu M. Fukuta Y. Nada F. J. Am. Chem. Soc.  2001,  123:  8408 
  • 8a Thompson DP. Boudjouk P. J. Org. Chem.  1988,  53:  2109 
  • 8b Klayman DL. Griffin TS. J. Am. Chem. Soc.  1973,  95:  197 
  • 8c Gladysz JA. Hornby JL. Garbe JE. J. Org. Chem.  1978,  43:  1204 
  • 9 This structure is novel. There is only one example of preparation of pyrido[3,2-e]-1,3-selenazine and pyrido[3,4-e]-1,3-selenazine ring compounds, see: Kristian P. Koscik D. Gonda J. Collect. Czech. Chem. Commun.  1983,  48:  3567 
  • Two patents regarding 2-thioxo-1,3-selenazolidin-4-one have appeared see, (a) and (b), while (b) also reports 2-selenoxo-1,3-selenazolidin-4-ones:
  • 10a Suga T, Mine K, Takahashi Y, and Fujimori N. inventors; JP  50071325.  1975; Chem. Abstr. 1976, 52086
  • 10b Sieglitz A, and Heimke P. inventors; DE  700555.  1942
  • 12a Casar Z. Leban I. Majcen-Le Marechal A. Lorcy D. J. Chem. Soc., Perkin Trans. 1  2002,  1568 
  • 12b Koketsu M. Nada F. Ishihara H. Synthesis  2002,  195 
  • 12c Brown GA. Anderson KMM. Murray KM. Gallagher T. Hales NJ. Tetrahedron  2000,  56:  5579 
  • 12d Cruz A. Macias-Mendoza D. Barragan-Rodriguez E. Tlahuext H. Noth H. Contreras R. Tetrahedron: Asymmetry  1997,  8:  3903 
11

CCDC 298139 for 4a contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.