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Synthesis 2001(16): 2427-2430
DOI: 10.1055/s-2001-18721
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Properties of O-Vinylamidoximes

Boris A. Trofimov*a, Elena Yu. Schmidta, Alexander M. Vasil’tsova, Al’bina I. Mikhalevaa, Alexey B. Zaitseva, Ludmila V. Morozovaa, Alexander G. Gorshkova, Jochem Henkelmannb, Jan-Dirk Arndtb
a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation
Fax: +7(395)2396046; e-Mail: bat@irioch.irk.ru;
b BASF AG, Ammoniaklaboratorium ZAR/C-M 311, 67056 Ludwigshafen, Germany
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Publication History

Received 21 August 2001
Publication Date:
05 August 2004 (online)

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Abstract

O-Vinylamidoximes 2 are synthesized from amidoximes 1 and acetylene in superbase systems (KOH/DMSO, KOH/NMP, NaOH/CsF/NMP) in a preparative yield of up to 80%. They decompose explosively above 150 °C, being resistant to solvolysis in the KOH/DMSO system (100 °C, 3 h) and to polymerization (AIBN, UV). Trifluoroacetylation of O-vinylbenzamidoxime 2b with (CF3CO)2O/pyridine gives 5-trifluoromethyl-3-phenyl-1,2,4-oxadiazole (3) in 49% yield.

Key words

O-vinylamidoximes - amidoximes - acetylene - heterocycle - superbase - vinylation - trifluoroacetylation

    References

  • 1 Trofimov BA. Mikhaleva AI. N-Vinylpyrroles   Nauka; Novosibirsk: Katritzky AR. San Diego Press   1984.  p.90-101   (in Russian)
    Google Scholar
  • 2 Trofimov BA. Adv. Heterocycl. Chem.  1990,  51:  280 
    Google Scholar
  • 3 Bean GP. In The Chemistry of Heterocyclic Compounds, Pyrroles   Part 1, Vol. 48:  Jones RA. Wiley; New York: 1990.  p.153-155  
    Google Scholar
  • 4 Trofimov BA. In The Chemistry of Heterocyclic Compounds, Pyrroles   Part 2, Vol. 48:  Wiley; New York: 1992.  p.131-298 
    Google Scholar
  • 5 Trofimov BA. Mikhaleva AI. Vasil’tsov AM. Schmidt EYu. Tarasova OA. Morozova LV. Sobenina LN. Preiss T. Henkelmann J. Synthesis  2000,  1125 
    Article in Thieme ConnectGoogle Scholar
  • 6 Trofimov BA. Schmidt EYu. Mikhaleva AI. Vasil’tsov AM. Larina LI. Klyba LV. Mendeleev Commun.  1999,  238 
    CrossrefGoogle Scholar
  • 7 Vasil’tsov AM. Schmidt EYu. Mikhaleva AI. Zaitsev AB. Tarasova OA. Afonin AV. Torjashinova D.-SD. Il′icheva LN . Trofimov BA. Russ. J. Org. Chem.  2001,  37:  334 
    CrossrefGoogle Scholar
  • 8 Sohlberg K. Leary SP. Owen NL. Trofimov BA. Vibrational Spectroscopy  1997,  227 
    CrossrefGoogle Scholar
  • 9 Afonin AV. Ushakov IA. Zinchenko SV. Tarasova OA. Trofimov BA. Magnetic Res. Chem.  2000,  38:  994 
    Google Scholar
  • 10 Heindel ND. Chun MC. Tetrahedron Lett.  1971,  1439 
    CrossrefGoogle Scholar
  • 11a Volkov AN. Sokolyanskaya LV. Trofimov BA. Izv. Akad. Nauk SSSR, Ser. Khim.  1976,  1430 
    Google Scholar
  • 12 Trofimov BA. Schmidt EYu. Mikhaleva AI. Vasil’tsov AM. Afonin AV. Mendeleev Commun.  2000,  29 
    CrossrefGoogle Scholar
  • 13 Baram GI. J. Chrom.  1996,  A 728:  387 
    Google Scholar
  • 14 Eloy F. Lenaers R. Chem. Rev.  1962,  62:  122 
    Google Scholar
  • 15 Witanovski M. Stefaniak L. Webb GA. In Annual Reports on NMR Spectroscopy   Vol. 11B:  Webb GA. Academic Press; London: 1981.  p.502 
    Google Scholar
  • 16 Chemical Applications of Spectroscopy   West W. Interscience Publishers; New York: 1956. 
    Google Scholar