Chemistry of Heterocyclic Compounds

, Volume 33, Issue 12, pp 1393–1399 | Cite as

Polyfuryl(aryl)alkanes and their derivatives

15. Products from the reduction of 2-nitroaryl-difurylmethanes. Synthesis of indole derivatives
  • A. V. Butin
  • T. A. Stroganova
  • V. T. Abaev
  • V. E. Zavodnik
Article

Abstract

The reduction of 2-nitrophenyldifurylmethane with SnCl2 leads to an indolenyl ketone as a result of intramolecular heterocycloaddition of the intermediately formed nitroso derivative. During the reduction of 2-nitroaryldifurylmethanes in the Zn+HCl or NH2NH2·H2O+Pd/C systems, 2-aminoaryldifurylmethanes are formed; when treated with trityl perchlorate, their acetyl derivatives are converted into indolo[2,3-h]-1-oxazulenium perchlorates.

Keywords

Organic Chemistry Ketone Alkane Acetyl Perchlorate 

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References

  1. 1.
    A. V. Butin, T. A. Stroganova, and V. G. Kul'evich, Khim. Geterotsikl. Soedin., No. 6, 738 (1996).Google Scholar
  2. 2.
    G. Jones and W. H. McKinley, Tetrahedron Lett., No. 28, 2457 (1977).Google Scholar
  3. 3.
    G. Jones and W. H. McKinley, J. Chem. Soc. Trans. Perkin I, No. 3, 599 (1979).Google Scholar
  4. 4.
    A. V. Butin, G. D. Krapivin, V. E. Zavodnik, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 5, 616 (1993).Google Scholar
  5. 5.
    A. V. Butin, V. T. Abaev, V. E. Zavodnik, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 5, 627 (1993).Google Scholar
  6. 6.
    A. V. Butin, V. T. Abaev, and T. A. Stroganova, Khim. Geterotsikl. Soedin., No. 11, 1578 (1995).Google Scholar
  7. 7.
    T. A. Stroganova, A. V. Butin, V. T. Abaev, and V. E. Zavodnik, Khim. Geterotsikl. Soedin., No. 2, 168 (1996).Google Scholar
  8. 8.
    M. Bartra, P. Romea, F. Urpi, and J. Vilarrasa, Tetrahedron46, 587 (1990).Google Scholar
  9. 9.
    S. J. Danishefsky and J. M. Schkeryantz, Synlett., No. 5, 475 (1995).Google Scholar

Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • A. V. Butin
  • T. A. Stroganova
  • V. T. Abaev
  • V. E. Zavodnik

There are no affiliations available

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