Intramolecular cyclization of 2-(<i>o</i>-carboran-1-yl) methylthio-3-cyanopyridines in basic conditions

Authors

  • А. А. Семиошкин A. N. Nesmeyanov Institute of Elementoorganic Chemistry, Russian Academy of Sciences, Moscow 117813
  • B. А. Артемов N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913
  • В. Л. Иванов A. N. Nesmeyanov Institute of Elementoorganic Chemistry, Russian Academy of Sciences, Moscow 117813
  • Г. M. Пташиц A. N. Nesmeyanov Institute of Elementoorganic Chemistry, Russian Academy of Sciences, Moscow 117813
  • П. B. Петровский A. N. Nesmeyanov Institute of Elementoorganic Chemistry, Russian Academy of Sciences, Moscow 117813
  • А. M. Шестопалов N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913
  • B. И. Брегадзе A. N. Nesmeyanov Institute of Elementoorganic Chemistry, Russian Academy of Sciences, Moscow 117813
  • B. П. Литвинов N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913

Abstract

Substituted 2-(o-carboran-1-yl)methylthio-3-cyanopyridines and-pyrimidines undergo Thorpe-Ziegler cyclization under the influence of KOH in DMF to give the corresponding thienopyridines and thienopyrimidines. The reaction is complicated by a side reaction in which thecloso-carborane nucleus is converted to anido-system. The yield of thienopyridines containing acloso-carborane unit is increased by introduction of an acceptor substituent in the pyridine ring. Destruction of thecloso-carborane nucleus is not observed with the pyrimidine derivatives. The structures of the series of new carborane-containing thienopyridines and pyrimidines was confirmed by spectroscopic methods.

How to Cite
Semioshkin, A. A.; Artemov, V. A.; Ivanov, V. L.; Ptashits, G. M.; Petrovskii, P. V.; Shestopalov, A. M.; Bregadze, V.I.; Litvinov, V. P. Chem. Heterocycl. Compd. 1998, 34, 688. [Khim. Geterotsikl. Soedin. 1998, 34, 790.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02252277

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Published

1998-06-25

Issue

No. 6 (1998)

Section

Original Papers