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Chemistry of Heterocyclic Compounds

, Volume 34, Issue 6, pp 688–691 | Cite as

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

  • A. A. Semioshkin
  • V. A. Artemov
  • V. L. Ivanov
  • G. M. Ptashits
  • P. V. Petrovskii
  • A. M. Shestopalov
  • V. I. Bregadze
  • V. P. Litvinov
Article

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.

Keywords

Organic Chemistry Pyridine Pyrimidine Side Reaction Spectroscopic Method 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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    A. A. Semioshkin, G. M. Ptashits, V. L. Ivanov, V. A. Artymova, A. M. Shestopalov, V. I. Bregadze, and V. P. Litvinov, Tetrahedron,53, 7911 (1997).Google Scholar
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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • A. A. Semioshkin
  • V. A. Artemov
  • V. L. Ivanov
  • G. M. Ptashits
  • P. V. Petrovskii
  • A. M. Shestopalov
  • V. I. Bregadze
  • V. P. Litvinov

There are no affiliations available

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