REACTION OF 1-SUBSTITUTED TETRAHYDRO-β-CARBOLINES WITH ACTIVATED ALKYNES – A NEW ORIGINAL APPROACH TO THE SYNTHESIS OF TETRAHYDROAZOCINO[5,4-<i>b</i>]INDOLES

Authors

  • Л. Г. Воскресенский Peoples' Friendship University of Russia, 117198 Moscow
  • Т. Н. Борисова Peoples' Friendship University of Russia, 117198 Moscow
  • Л. Н. Куликова Peoples' Friendship University of Russia, 117198 Moscow
  • Е. Г. Долгова Peoples' Friendship University of Russia, 117198 Moscow
  • А. И. Клейменов Peoples' Friendship University of Russia, 117198 Moscow
  • Е. А. Сорокина Peoples' Friendship University of Russia, 117198 Moscow
  • А. А. Титов Peoples' Friendship University of Russia, 117198 Moscow
  • А. В. Варламов Peoples' Friendship University of Russia, 117198 Moscow

DOI:

https://doi.org/10.1007/7524

Keywords:

azocino[5, 4-b]indoles, 2-alkoxyalkylindoles, activated alkynes, tetrahydro-β-carbolines, ring expansion

Abstract

The transformations of  1-substituted tetrahydro-β-carbolines by the action of activated alkynes were studied. The action of dimethyl acetylenedicarboxylate in methanol gives products of the opening of the tetrahydropyridine fragment, namely, 2-methoxyalkylindoles. The action of ethyl propiolate in ethanol and of tosylacetylene in methanol gives mixtures of azocino[5,4-b]indoles and 2-alkoxyindoles. The action of ethyl propiolate in acetonitrile gives azocinoindoles.

How to Cite
Voskressensky, L. G.; Borisova, T. N.; Kulikova, L. N.; Dolgova, E. G.; Kleimenov, A. I.; Sorokina, E. A.; Titov, A. A.; Varlamov, A. V.  Chem. Heterocycl. Compd. 2007, 43, 587. [Khim. Geterotsikl. Soedin. 2007, 703.]

For this article in the English edition see DOI 10.1007/s10593-007-0093-y


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Published

2023-03-21

Issue

No. 5 (2007)

Section

Original Papers