Chemistry of Heterocyclic Compounds

, Volume 28, Issue 3, pp 266–268 | Cite as

Synthesis of 4H-pyrans by O-cyclization of 1,5-diketones

  • A. F. Blinokhvatov
  • O. V. Markovtseva
  • M. N. Nikolaeva
Article

Abstract

Substituted 4H-pyrans were obtained in high preparative yields by the reaction of 1,5-diketones with acetic anhydride and boron trifluoride etherate in diethyl ether. It is assumed that the heterocyclization of 1,5-diketones includes a step involving the formation and transformations of an acyloxy carbonium ion.

Keywords

Acetic Ether Organic Chemistry Boron Anhydride 

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Literature cited

  1. 1.
    E. E. Blaise and H. Gault, Bull. Soc. Chim. France, No. 1, 129 (1907).Google Scholar
  2. 2.
    V. G. Kharchenko and S. N. Chalaya, 1,5-Diketones, Izd. Saratovsk. Univ., Saratov (1977).Google Scholar
  3. 3.
    O. V. Drygina and A. D. Garnovskii, Khim. Geterotsikl. Soedin., No. 8, 1101 (1983).Google Scholar
  4. 4.
    A. Balaban and N. Bărbulescu, Rev. Roum. Chim., No. 11, 109 (1966).Google Scholar
  5. 5.
    N. N. Minaeva and M. N. Tilichenko, The Chemistry of Dicarbonyl Compounds [in Russian], Riga (1986), p. 141.Google Scholar
  6. 6.
    S. V. Borodaev, N. V. Shibaeva, O. V. Zubkova, A. P. Knyazev, S. M. Luk'yanov, and A. I. Pyshchev, Zh. Org. Khim., 25, 2416 (1989).Google Scholar
  7. 7.
    O. V. Drygina, G. N. Dorofeenko, and O. Yu. Okhlobystin, Zh. Obshch. Khim., 51, 868 (1981).Google Scholar
  8. 8.
    V. M. Thuy, C. Normant-Chefnay, P. Maitee, and H. Petit, Bull. Soc. Chim. France, No. 1, 241 (1975).Google Scholar
  9. 9.
    V. G. Kharchenko, N. M. Yakoreva, and N. I. Kozhevnikova, Zh. Org. Khim., No. 7, 1551 (1971).Google Scholar
  10. 10.
    K. Dimroth, W. Kinzebach, and M. Soyka, Chem. Ber., 99, 2351 (1966).Google Scholar
  11. 11.
    V. G. Kharchenko and A. F. Blinokhvatov, Khim. Geterotsikl. Soedin., No. 12, 1615 (1978).Google Scholar
  12. 12.
    K. F. Suzdalev and A. V. Koblik, Khim. Geterotsikl. Soedin., No. 5, 603 (1990).Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • A. F. Blinokhvatov
    • 1
  • O. V. Markovtseva
    • 1
  • M. N. Nikolaeva
    • 1
  1. 1.Penza Agricultural InstitutePenza

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