Download PDF
Synthesis 2001(13): 1959-1964
DOI: 10.1055/s-2001-17701
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of 5-Trichloromethyl-5-hydroxy-3-heteroalkyl-4,5-dihydroisoxazoles

Marcos A. P. Martins*, Adilson P. Sinhorin, Nilo E. K. Zimmermann, Nilo Zanatta, Helio G. Bonacorso, Giovani P. Bastos
Núcleo de Química de Heterociclos, Departamento de Quimica, Universidade Federal de Santa Maria, 97.105-900 Santa Maria, RS, Brazil
Fax: +55 55 2208031; e-Mail: mmartins@base.ufsm.br;
Further Information

Publication History

Received 29 March 2001
Publication Date:
10 August 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

A synthetic strategy to obtain a series of 3-heteroalkyl-4,5-dihydroisoxazoles, which is based on the cyclocondensation reaction of 5-heteroalkyl-1,1,1-trichloro-4-methoxy-3-penten[hexen]-2-ones 1a-g, 2a-g with hydroxylamine has been developed. The preparation of 1,1,1-trichloro-5-heteroalkyl-4-methoxy-3-penten[hexen]-2-ones in good yields is also described.

Key words

isoxazoles - oxygen heterocycles - enones - enol ethers - halogen compounds

    References

  • 1 Gombos Z. Nyitrai J. Doleschall G. Kolonits P. Párkányi L. Kálmán A. J. Chem. Soc. Perkin Trans.  1993,  1:  139 
    Google Scholar
  • 2 Pavarelo P. Varasi M. Synth. Commun.  1992,  22:  1939 
    Google Scholar
  • 3 Dannhardt G. Kiefer W. Lambrecht G. Eur. J. Med. Chem.  1995,  30:  839 
    CrossrefGoogle Scholar
  • 4 Martins MAP. Colla A. Clar G. Krimmer S. Fischer P. Synthesis  1991,  6:  483 
    Article in Thieme ConnectGoogle Scholar
  • 5a Martins MAP. Bastos GP. Bonacorso HG. Zanatta N. Flores AFC. Siqueira GM. Tetrahedron Lett.  1999,  40:  4309 
    CrossrefGoogle Scholar
  • 5b Bonacorso HG. Martins MAP. Bittencourt SRT. Lourega RV. Zanatta N. Flores AFC. J. Fluorine Chem.  1999,  99:  177 
    CrossrefGoogle Scholar
  • 6a Martins MAP. Zoch AN. Bonacorso HG. Zanatta N. Clar GJ. Heterocycl. Chem.  1995,  32:  739 
    Google Scholar
  • 6b Martins MAP. Flores AC. Freitag R. Zanatta N. J. Heterocycl. Chem.  1995,  32:  731 
    Google Scholar
  • 6c Martins MAP. Flores AC. Freitag R. Zanatta N. J. Heterocycl. Chem.  1996,  33:  1223 
    Google Scholar
  • 6d Martins MAP. Siqueira GM. Bastos GP. Zanatta N. J. Heterocycl. Chem.  1996,  33:  1619 
    Google Scholar
  • 6e Martins MAP. Braibante MEF. Clar G. J. Heterocycl. Chem.  1993,  30:  1159 
    Google Scholar
  • 7a Zanatta N. Pacholski IL. Blanco I. Martins MAP. J. Braz. Chem. Soc.  1991,  1:  18 
    CrossrefGoogle Scholar
  • 7b Zanatta N. Madruga CC. Clerici E. Martins MAP. J. Heterocycl. Chem   1995,  32:  735 
    CrossrefGoogle Scholar
  • 7c Zanatta N. Cortelini MF. Carpes MJS. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  1997,  34:  1 
    CrossrefGoogle Scholar
  • 7d Bonacorso HG. Bittencourt ST. Wastowski AD. Wentz AP. Zanatta N. Martins MAP. Tetrahedron Lett.  1996,  37:  9155 
    CrossrefGoogle Scholar
  • 7e Zanatta N. Fagundes MB. Ellenshon R. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  1998,  35:  451 
    CrossrefGoogle Scholar
  • 8a Martins MAP. Flores AFC. Bastos GP. Sinhorin AP. Bonacorso HG. Zanatta N. Tetrahedron Lett.   2000,  41:  293 
    Article in Thieme ConnectGoogle Scholar
  • 8b Martins MAP. Freitag RA. Rosa A. Flores AFC. Zanatta N. Bonacorso HG. J. Heterocycl. Chem.  1995,  32:  731 
    Article in Thieme ConnectGoogle Scholar
  • 8c Martins MAP. Freitag RA. Flores AFC. Zanatta N. Synthesis  1995,  1491 
    Article in Thieme ConnectGoogle Scholar
  • 9 Katritzky AR. Rees CW. Comprehensive Heterocycl. Chem. (1-8)   Potts KT. Pergamon Press; Oxford: 1984. 
    Google Scholar
  • 10 Bizzi A. Codegoni AM. Garattini S. Il Farmaco- Ed. Sc.  1967,  12:  716-909  
    Google Scholar
  • 11a Bellioti T, Connor D, Flynn DL, Kostlan CR, and Nies D. inventors; Patente da Warner-Lambert Co.  245825. 
  • 12a Izhii T, Shimotori H, and Ishikaawa K. inventors; Patente da Mitsui Toatsu Chemical  ✓2✗210. 
  • 13a Linderman RJ. Jamois EA. Tennyson SD. J. Org. Chem.  1994,  59:  957 
    Google Scholar
  • 13b Nenajdenko VG. Balenkova ES. Khim. Geterotsikl. Soedin.  1994,  10:  1429 
    Google Scholar
  • 14 Kamitor Y. Hojo M. Masuda RJ. Heterocycl. Chem.  1993,  30:  389 
    Google Scholar
  • 15 Nenajdenko VG. Sanin AV. Balenkova ES. Molecules  1997,  146 
    CrossrefGoogle Scholar
  • 16 Spiegler W. Götz N. Synthesis  1986,  69 
    Article in Thieme ConnectGoogle Scholar