Synthesis 2009(20): 3405-3410  
DOI: 10.1055/s-0029-1216962
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Approach to the Synthesis of 3-Substituted 4-(Diethoxy­phosphoryl)isoxazoles from 3-Azidoalka-1,3-dienylphosphonates

Valery K. Brel*
Institute of Physiologically Active Compounds of Russian Academy of Sciences, Chernogolovka, Moscow region 142432, Russian Federation
Fax: +7(496)5249508; e-Mail: brel@ipac.ac.ru;
Further Information

Publication History

Received 11 March 2009
Publication Date:
21 August 2009 (online)

Abstract

New 3-azidoalka-1,3-dienylphosphonates were synthesized by a convenient and efficient method. These compounds are useful as intermediates in the preparation of 3-(3-aryl-4,5-di­hydroisoxazol-5-yl)- and 3-alkenyl-4-(diethoxyphosphoryl)isoxazoles.

    References

  • 1 Dileep Kurman JS. Ho MM. Leung JM. Toyokuni T. Adv. Synth. Catal.  2002,  344:  1146 
  • 2 Hagiwara Y. Tanaka M. Kajitani A. Yasumoto S. JP 3,220,180 1991; Chem. Abstr. 1992, 116, 128944
  • 3 Minami N, Sato M, Hasumi K, Yamamoto N, Keino K, Matsui T, Kaneda A, Ota S, Saito N, Sato S, Asadori A, Doi S, Kobayashi M, Sato J, and Asano S. inventors; JP  2000,086,657.  ; Chem. Abstr. 2000, 132, 251139
  • 4 Dannhardt G. Dominiak P. Laufer S. Arzneim.-Forsch.  1993,  43:  441 
  • 5 Skolnick P. J. Clin. Psychiatry  2002,  63:  19 
  • 6 Scheen AJ. Malaise M. Rev. Med. Liege  2004,  59:  251 
  • 7 Chen Q. Liu F. Xu F. Yang C. J. Heterocycl. Chem.  2008,  45:  77 
  • 8 Eskandari R. Navidpour L. Amini M. Shafaroodi H. Shafiee A. J. Heterocycl. Chem.  2007,  44:  449 
  • 9 Brel VK. Heteroat. Chem.  2006,  17:  547 
  • 10 Brel VK. Synthesis  2007,  2674 
  • 11a Brel VK. Synthesis  1998,  710 
  • 11b Brel VK. Stang PJ. Eur. J. Org. Chem.  2003,  512 
  • 12a Brandsma L. Preparative Acetylenic Chemistry   Elsevier; Amsterdam: 1988.  p.265 
  • 12b Brel VK. Synthesis  1999,  463 
  • 13 Mark V. Tetrahedron Lett.  1962,  3:  281 
  • 14 Brel VK. Belsky VK. Stash AI. Zavodnik VE. Stang PJ. Eur. J. Org. Chem.  2005,  512