Download PDF
Synthesis 2006(4): 706-710  
DOI: 10.1055/s-2006-926312
PAPER
© Georg Thieme Verlag Stuttgart · New York

Application of a Thermal β-Elimination Reaction to N-Alkoxy-3,3-dinitro­isoxazolidines: Synthesis of 3-Nitroisoxazolines

Olga A. Ivanova, Ekaterina M. Budynina, Elena B. Averina, Tamara S. Kuznetsova*, Nikolai S. Zefirov
Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia
Fax: +7(95)9390290; e-Mail: kuzn@org.chem.msu.ru;
Further Information

Publication History

Received 2 June 2005
Publication Date:
25 January 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

A facile general method has been developed for the synthesis of 5-substituted 3-nitroisoxazolines by the application of a thermal β-elimination reaction to N-alkoxy-3,3-dinitroisoxazolidines in chlorobenzene.

Key words

β-elimination - [3+2] cycloaddition - isoxazolines - isoxazolidines - heterocycles

    References

  • 1a Lang SA. Lin Y.-i. Isoxazoles and Their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry   Katritzky AR. Rees CW. Pergamon; New York: 1984.  p.1 
  • 1b Boyer JH. Organic Nitro Chemistry Series 1, Nitroazoles. The C-Nitro Derivatives of Five-Membered N- and N,O-Heterocycles   VCH; Deerfield Beach: 1986.  p.301 
  • 2 Uhr H, Kretschik O, Kugler M, and Wachtler P. inventors; PCT Int Appl. WO  2002034731.  ; Chem. Abstr. 2002, 136, 340670
  • 3 Bay PG. inventors; US Patent  3207761.  ; Chem. Abstr. 1965, 63, 18093c
  • 4a Löher H.-J, Bauer K, and Bieringer H. inventors; US Patent  5536698. 
  • 4b Reddy MVR, and Bell SC. inventors; US Patent  0162813. 
  • 5 Wade PA. J. Org. Chem.  1978,  43:  2020 
    CrossrefSearch in Google Scholar
  • 6 Shvekhgeimer GA. Sobtsova NI. Baranski A. Rocz. Chem.  1972,  46:  1543 
    Search in Google Scholar
  • 7 Diamanti G. Duranti E. Tontini A. Synthesis  1993,  1104 
    Thieme Connect
  • 8a Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products   Padwa A. Pearson WH. Wiley; Hoboken, New Jersey: 2002. 
  • 8b Torssell KBG. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis   VCH Publishers; New York: 1988. 
  • 9 Tartakovskii VA. Onishchenko AA. Chlenov IE. Novikov SS. Dokl. Chem. (Engl. Transl.)  1966,  167:  406 ; Chem. Abstr. 1966, 64: 2079e
    Search in Google Scholar
  • 10 Tartakovskii VA. Chlenov IE. Morozova NS. Novikov SS. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1966,  346 ; Chem. Abstr. 1966, 64, 17567e
  • 11 Ivanova OA. Averina EB. Grishin YuK. Kuznetsova TS. Korlyukov AA. Antipin MYu. Zefirov NS. Dokl. Chem. (Engl. Transl.)  2002,  382:  21 ; Chem. Abstr. 2002, 137, 337505
    CrossrefSearch in Google Scholar
  • 12 Budynina EM. Ivanova OA. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Dokl. Chem. (Engl. Transl.)  2002,  382:  16 ; Chem. Abstr. 2003, 138, 4478
    CrossrefSearch in Google Scholar
  • 13 Budynina EM. Ivanova OA. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Dokl. Chem. (Engl. Transl.)  2002,  387:  304 ; Chem. Abstr. 2003, 138, 304197
    CrossrefSearch in Google Scholar
  • 14 Averina EB. Budynina EM. Ivanova OA. Grishin YuK. Gerdov SM. Kuznetsova TS. Zefirov NS. Russ. J. Org. Chem. (Engl. Transl.)  2004,  40:  162 ; Chem. Abstr. 2005, 142, 155884
    CrossrefSearch in Google Scholar
  • 15 Budynina EM. Ivanova OA. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis  2005,  286 
    Thieme Connect
  • 16 Averina EB. Ivanova OA. Grishin YuK. Kuznetsova TS. Zefirov NS. Russ. J. Org. Chem. (Engl. Transl.)  2000,  36:  1562 ; Chem. Abstr. 2001, 135, 137070
    Search in Google Scholar
  • 17 Altukhov KV. Tartakovskii VA. Perekalin VV. Novikov SS. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1967,  192 ; Chem. Abstr. 1967, 66, 115635r.
  • 18 Andreeva LM. Altukhov KV. Perekalin VV. J. Org. Chem. USSR (Engl. Transl.)  1969,  5:  212 ; Chem. Abstr. 1969, 70, 106419d
    Search in Google Scholar