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.
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E. E. Blaise and H. Gault, Bull. Soc. Chim. France, No. 1, 129 (1907).
V. G. Kharchenko and S. N. Chalaya, 1,5-Diketones, Izd. Saratovsk. Univ., Saratov (1977).
O. V. Drygina and A. D. Garnovskii, Khim. Geterotsikl. Soedin., No. 8, 1101 (1983).
A. Balaban and N. Bărbulescu, Rev. Roum. Chim., No. 11, 109 (1966).
N. N. Minaeva and M. N. Tilichenko, The Chemistry of Dicarbonyl Compounds [in Russian], Riga (1986), p. 141.
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).
O. V. Drygina, G. N. Dorofeenko, and O. Yu. Okhlobystin, Zh. Obshch. Khim., 51, 868 (1981).
V. M. Thuy, C. Normant-Chefnay, P. Maitee, and H. Petit, Bull. Soc. Chim. France, No. 1, 241 (1975).
V. G. Kharchenko, N. M. Yakoreva, and N. I. Kozhevnikova, Zh. Org. Khim., No. 7, 1551 (1971).
K. Dimroth, W. Kinzebach, and M. Soyka, Chem. Ber., 99, 2351 (1966).
V. G. Kharchenko and A. F. Blinokhvatov, Khim. Geterotsikl. Soedin., No. 12, 1615 (1978).
K. F. Suzdalev and A. V. Koblik, Khim. Geterotsikl. Soedin., No. 5, 603 (1990).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 320–322, March, 1992.
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Blinokhvatov, A.F., Markovtseva, O.V. & Nikolaeva, M.N. Synthesis of 4H-pyrans by O-cyclization of 1,5-diketones. Chem Heterocycl Compd 28, 266–268 (1992). https://doi.org/10.1007/BF00529364
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DOI: https://doi.org/10.1007/BF00529364