Abstract
Reaction of 2-hydroxybenzaldehydes with α-methylfuran (sylvan) under acid-catalysis conditions was investigated. It is shown that the reaction does not stop at the step involving formation of 2-hydroxyarylfuryl-methanes but proceeds further with opening of one of furan rings and recyclization to 3-furylbenzo-furan derivatives. The latter in turn undergo transformations that lead to new heterocyclic systems — 5,6-dihydro-2,4-dimethyl-4-(5-methyl-2-furyl)-4H-benzo[b]furo[2,3-h]cyclopenta[b]furans. Data from the IR, PMR, and mass spectra, alternative synthesis, and x-ray diffraction analysis were used to confirm structures of the synthesized compounds.
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A. V. Butin, G. D. Krapivin, V. G. Kul'nevich, V. E. Vorontsov, and V. I. Bakhmutov, Khim. Geterotsikl. Soedin., No. 4, 450 (1993).
A. V. Butin, V. E. Zavodnik, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 7, 997 (1992).
S. V. Zhuravlev and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 5, 597 (1983).
S. V. Zhuravlev and V. G. Kul'nevich, Proceedings of the Krasnodar Polytechnical Institute on the Chemistry and Technology of Furan Compounds [in Russian], Krasnodar (1982), p. 163.
S. P. Voronin, T. I. Gubina, I. A. Markushina, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 10, 1333 (1989).
E. J. Stamhuis, W. Drenth, H. van den Berg, Rec. Trav. Chem., 83, No. 2, 167 (1964).
M. J. Kamlet and R. W. Taft, J. Org. Chem., 47, 1734 (1982).
K. Reichardt, Solvents and Effects of the Medium in Organic Chemistry [Russian translation], Mir, Moscow (1991).
H. Günther, Introductory Course in NMR Spectroscopy [Russian translation], Mir, Moscow (1984).
G. Emsley, G. Feeney, and L. Sutcliff, High-Resolution NMR Spectroscopy [Russian translation], Vol. 2, Mir, Moscow (1969), p. 33.
R. Johnson, Handbook of Mass Spectrometry for Organic Chemists [Russian translation], Mir, Moscow (1975).
E. B. Usova, G. D. Krapivin, V. E. Zavodnik, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 7, 931 (1990).
U. Burkert and N. Allinger, Molecular Mechanics [Russian translation], Mir, Moscow (1986).
G. M. Sheldrick, Computational Crystallography, Oxford University Press, New York-Oxford (1982), p. 506.
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For Communication 6 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 616–626, May, 1993.
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Butin, A.V., Krapivin, G.D., Zavodnik, V.E. et al. Polyfuryl(aryl)alkanes and their derivatives. 7. New recyclization and cyclization reactions in the 2-hydroxyaryldifurylmethane series. Chem Heterocycl Compd 29, 524–533 (1993). https://doi.org/10.1007/BF00534462
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DOI: https://doi.org/10.1007/BF00534462