PDF herunterladen
Synthesis 2010(3): 407-414  
DOI: 10.1055/s-0029-1218594
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and [3+2] Cycloadditions of 3-Bromo-5,6-dihydro-4H-1,2-oxazine N-Oxides

Leonid V. Romashova, Yulya A. Khomutovab, Vitaliy M. Danilenkoa, Sema L. Ioffeb, Alexey V. Lesiv*a
a Moscow Chemical Lyceum, Tamojenny pr. 4, 111033 Moscow, Russian Federation
b N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
Fax: +7(495)3623440; e-Mail: Lesav@mail.ru;
Weitere Informationen

Publikationsverlauf

Received 14 September 2009
Publikationsdatum:
07. Dezember 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A number of 3-bromo-5,6-dihydro-4H-1,2-oxazine N-oxides have been synthesized and subjected to [3+2] cycloaddition with alkenes affording various types of products: 3-vinyloxazolines, isoxazoline N-oxides, and 3-functionalized 1,2-oxazine N-oxides.

Key words

1,2-oxazine N-oxide - isoxazoline - cycloaddition - nitronates­ - nitroso acetals

    References

  • 1 Ioffe SL. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, In Novel Strategies in Synthesis   2nd ed.:  Feuer H. John Wiley & Sons; New Jersey: 2008.  p.658 
    Google Scholar
  • 2 Denmark SE. Montgomery JI. Kramps LA. J. Am. Chem. Soc.  2006,  128:  11620 ; and references therein
    CrossrefGoogle Scholar
  • 3a Chlenov IE. Petrova IM. Hasanov BN. Stepanyanc AU. Chigov OC. Tartakovskiy VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1978,  27:  2278 ; and references therein
    Google Scholar
  • 3b Chlenov IE. Petrova IM. Shitkin VM. Tartakovskiy VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1975,  24:  1365 
    Google Scholar
  • 3c Chlenov IE. Sokolova IL. Hasanov BN. Novikov VM. Karpenko NF. Stepanyanc AU. Tartakovskiy VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1974,  23:  347 
    Google Scholar
  • 4 Chlenov IE. Hudak VM. Kolymagina LN. Morozova NS. Tartakovskiy VA. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1970,  1757 
    CrossrefGoogle Scholar
  • 5 Denmark SE. Guagnano V. Dixon JA. Stolle A. J. Org. Chem.  1997,  62:  4610 
    CrossrefGoogle Scholar
  • 6a Tishkov AA. Lesiv AV. Khomutova YuA. Strelenko YuA. Nesterov ID. Antipin MYu. Ioffe SL. Denmark SE. J. Org. Chem.  2003,  68:  9477 
    Google Scholar
  • 6b Sukhorukov AYu. Klenov MS. Ivashkin PE. Lesiv AV. Khomutova YuA. Ioffe SL. Synthesis  2007,  97 
    Google Scholar
  • 7 Brook MA. Seebach D. Can. J. Chem.  1987,  65:  836 
    CrossrefGoogle Scholar
  • 8 Cycloaddition of 3-methyl-1,2-oxazine N-oxide proceeded at reflux in xylene within 8 h. This fact corresponds with the results obtained for [3+2] cycloaddition between alkenes and 3-halo silyl nitronates [k(F) >> k(Br) ≈ k(Cl) > k(I)]. Kunetsky RA. Dilman AD. Struchkova MI. Belyakov PA. Tartakovsky VA. Ioffe SL. Synthesis  2006,  2265 
    Artikel in Thieme ConnectGoogle Scholar
  • 9 Kirby AJ. Stereolectronic Effects   Oxford; New York: 1996.  p.24 
    Google Scholar
  • 10a Rudchenko VF. Chem. Rev.  1993,  93:  725 
    Google Scholar
  • 10b Lambert JB. Takeuchi Y. Cyclic Organonitrogen Stereodynamics   VCH; New York: 1992.  Chap. 7.1.1 and 7.2.1. and references therein
    Google Scholar
  • 11a Conti P. Dallanoce C. Amici MD. Micheli CD. Klotz K.-N. Bioorg. Med. Chem.  1998,  6:  401 
    Google Scholar
  • 11b Lam PYS. Adams JJ. Clark CG. Calhoun WJ. Luettgen JM. Knabb RM. Wexler RR. Bioorg. Med. Chem. Lett.  2003,  13:  1795 
    Google Scholar
  • 12 Worrall DE. Org. Synth. Coll. Vol. 1   John Wiley & Sons; London: 1941.  p.413 
    Google Scholar
  • 13 Aleksiev DI. Ivanova SM. Russ. J. Org. Chem.  1993,  29:  1845 
    Google Scholar
  • 14 Pfeiffer P. Chem. Ber.  1914,  47:  1755 ; see p. 1768
    CrossrefGoogle Scholar