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Synthesis 2009(18): 3099-3105  
DOI: 10.1055/s-0029-1216907
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reaction of N,N-Dioxyenamines with Anhydrides of Carboxylic and Sulfonic Acids; A New Method for the Synthesis of α-Hydroxyoxime Derivatives

Andrey A. Tabolin, Alexey V. Lesiv*, Sema L. Ioffe
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: lesav@mail.ru;
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Publication History

Received 16 April 2009
Publication Date:
14 July 2009 (online)

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Abstract

The reactions of N,N-dioxyenamines with carboxylic and sulfonic acid anhydrides were investigated. A new method for the synthesis of α-hydroxyoxime derivatives via the reaction of N,N-dioxyenamines with trifluoroacetic anhydride is described.

Key words

1,2-oxazine - trifluoroacetic anhydride - hydroxyoxime - enamine - rearrangement

    References

  • 1 Tishkov AA. Lesiv AV. Khomutova YuA. Strelenko YuA. Nesterov ID. Antipin MYu. Ioffe SL. Denmark SE. J. Org. Chem.  2003,  68:  9477 
    CrossrefGoogle Scholar
  • 2a Dilman AD. Tishkov AA. Lyapkalo IM. Ioffe SL. Strelenko YuA. Tartakovsky VA. Synthesis  1998,  181 
    Google Scholar
  • 2b Dilman AD. Tishkov AA. Lyapkalo IM. Ioffe SL. Kachala VV. Strelenko YuA. Tartakovsky VA. J. Chem. Soc., Perkin Trans. 1  2000,  2926 
    Google Scholar
  • 3 Dilman AD. Lyapkalo IM. Ioffe SL. Strelenko YuA. Tartakovsky VA. J. Org. Chem.  2000,  65:  8826 
    CrossrefGoogle Scholar
  • 4 Dilman AD. Ioffe SL. Mayr H. J. Org. Chem.  2001,  66:  3196 
    CrossrefPubMedGoogle Scholar
  • 5 Kunetsky RA. Dilman AD. Struchkova MI. Tartakovsky VA. Ioffe SL. Tetrahedron Lett.  2005,  46:  5203 
    CrossrefGoogle Scholar
  • 6 Ustinov AV. Dilman AD. Ioffe SL. Strelenko YuA. Smit WA. Tartakovsky VA. Mendeleev Commun.  2003,  13:  74 
    CrossrefGoogle Scholar
  • 7 Dilman AD. Lyapkalo IM. Ioffe SL. Strelenko YuA. Tartakovsky VA. Synthesis  1999,  1767 
    Article in Thieme ConnectGoogle Scholar
  • 8a Feger H. Simchen G. Liebigs Ann. Chem.  1986,  3:  1456 
    Google Scholar
  • 8b Makarenkova LM. Bliznets IV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Russ. Chem. Bull.  2000,  49:  1261 
    Google Scholar
  • 8c Lesiv AV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Helv. Chim. Acta  2002,  85:  3489 
    Google Scholar
  • 8d Semakin AN. Sukhorukov AYu. Lesiv AV. Khomutova YuA. Ioffe SL. Lyssenko KA. Synthesis  2007,  2862 
    Google Scholar
  • 8e Lesiv AV. Ioffe SL. Strelenko YuA. Danilenko VM. Russ. Chem. Bull.  2004,  10:  2233 
    Google Scholar
  • 9 Lesiv AV. Ioffe SL. Strelenko YuA. Bliznets IV. Tartakovsky VA. Mendeleev Commun.  2002,  12:  99 
    CrossrefGoogle Scholar
  • 10 Ustinov AV. Dilman AD. Ioffe SL. Belyakov PA. Strelenko YuA. Russ. Chem. Bull.  2002,  8:  1455 
    Google Scholar
  • 11 Sukhorokov AYu. Bliznets IV. Lesiv AV. Khomutova YuA. Strelenko TuA. Ioffe SL. Synthesis  2005,  1077 
    Article in Thieme ConnectGoogle Scholar
  • 12 Lee JY. Hong Y.-T. Kim S. Angew. Chem. Int. Ed.  2006,  45:  6182 
    CrossrefGoogle Scholar
  • 14a Tabolin AA. Lesiv AV. Khomutova YuA. Belyakov PA. Strelenko YuA. Ioffe SL. Synthesis  2005,  1656 
    Google Scholar
  • 14b Feger H. Simchen G. Liebigs Ann. Chem.  1986,  428 
    Google Scholar
  • 15 Klenov MS. Lesiv AV. Khomutova YuA. Nesterov ID. Ioffe SL. Synthesis  2004,  1159 
    Article in Thieme ConnectGoogle Scholar
  • 16 Tabolin AA. Lesiv AV. Khomutova YuA. Nelyubina YuV. Ioffe SL. Tetrahedron  2009,  65:  4578 
    CrossrefGoogle Scholar
  • For the substitution of silyl group by trifluoroacetyl see:
  • 18a Aubert C. Begue J.-P. Synthesis  1985,  759 
    Google Scholar
  • 18b Stamatov SD. Stawinski J. Synlett  2007,  439 
    Google Scholar
  • 20a Miyata O. Koizumi T. Asai H. Iba R. Naito T. Tetrahedron Lett.  2005,  46:  4015 
    Google Scholar
  • 20b Moutel S. Shipman M. Martin OR. Ikedac K. Asano N. Tetrahedron: Asymmetry  2005,  16:  487 
    Google Scholar
  • 20c Wan X. Doridot G. Joullie MM. Org. Lett.  2007,  9:  977 
    Google Scholar
  • 21a Marco JA. Carda M. Murga J. Rodrigues S. Falomir E. Oliva M. Tetrahedron: Asymmetry  1998,  9:  1679 
    Google Scholar
  • 21b Dransfield PJ. Gore PM. Prokes I. Shipman M. Slawin AMZ. Org. Biomol. Chem.  2003,  1:  2723 
    Google Scholar
  • 22a Hennebohle M. Le Roy P.-Y. Hein M. Ehrler R. Jager V. Z. Naturforsch., B: Chem. Sci.  2004,  59:  451 
    Google Scholar
  • 22b Demir AS. Sesenoglu O. Aksoy-Cam H. Kaya H. Aydogan K. Tetrahedron: Asymmetry  2003,  14:  1335 
    Google Scholar
  • 23a Tsoungas PS. Heterocycles  2002,  57:  915 
    Google Scholar
  • 23b Zimmer R. Collas M. Czerwonka R. Hain U. Reissig H.-U. Synthesis  2008,  237 
    Google Scholar
  • 24 Gottlieb HE. Kotlyar V. Nudelman A. J. Org. Chem.  1997,  62:  7512 
    CrossrefPubMedGoogle Scholar
  • 25 Almarego WLF. Chai CLL. In Purification of Laboratory Chemicals   5th ed.:  Elsevier; Oxford: 2003.  p.370 
    Google Scholar
  • 26 Kunetsky RA. Dilman AD. Struchkova MI. Belyakov PA. Tartakovsky VA. Ioffe SL. Synthesis  2006,  2265 
    Article in Thieme ConnectGoogle Scholar
  • 27 Kunetsky RA. Dilman AD. Ioffe SL. Struchkova MI. Strelenko YuA. Tartakovsky VA. Org. Lett.  2003,  5:  4907 
    CrossrefGoogle Scholar
13

For BENA nucleophilicity parameter N = 3-5 according to Professor Mayr’s scale, while for ‘classical’ enamines N = ≥ 11 (ref. 4).

17

Mikhailov, A. A.; Lesiv, A. V.; Ioffe, S. L. unpublished.

19

For discussion of the stereochemistry of the rearrangement of 2 see ref. 16.