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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 8, pp 1025–1031 | Cite as

Preparation of 4,4a,9,9a-tetrahydrocarbazoles and 1,3a,4,8b-tetra-hydrocyclopenta[b]indoles

  • R. R. Gataullin
  • R. R. Ishberdina
  • O. V. Shitikova
  • F. F. Minnigulov
  • L. V. Spirikhin
  • I. B. Abdrakhmanov
Article

Abstract

Halocyclization of mesylates or tosylates of 2-(cycloalk-2-en-1-yl)anilines gives N-methanesulfonyl-or N-toluenesulfonyl-1-halo-1,2,3,4,4a,9a-hexahydrocarbazoles, heating of which in DMF at 160°C or in piperidine at 110°C leads to 4,4a,9,9a-tetrahydro-3H-carbazoles. Heating N-methanesulfonyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole in DMF at 180—200°C gives 1,3a,4,9b-tetrahydrocyclopenta[b]indole, while in the presence of an ortho-methyl substituent the dehydroiodination reaction proceeds in piperidine at 110°C in high yield. The effect of the nature of the ortho substituent of N-methyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole on the conformational equilibrium of the cyclopentane ring has been established by 1H NMR spectroscopy.

Keywords

cyclopenta[b]indolines hexahydrocarbazoles tetrahydrocarbazoles halocyclization dehydroiodination conformation 

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References

  1. 1.
    J. A. Murphy, K. A. Scot, R. S. Sinclan, and N. Lewis, Tetrahedron Lett., 38, 7295 (1997).CrossRefGoogle Scholar
  2. 2.
    J. A. Murphy, F. Rasheed, S. Gastraldi, T. Ravishander, and N. Lewis, J. Chem. Soc., Perkin Trans. 1, 1549 (1997).Google Scholar
  3. 3.
    R. R. Gataullin, F. F. Minnigulov, A. A. Fatykhov, L. V. Spirikhin, I. B. Abdrakhmanov, Zh. Org. Khim., 37, 1357 (2001).Google Scholar
  4. 4.
    R. R. Gataullin, T. V. Kazhanova, F. F. Minnigulov, A. A. Fatykhov, L. V. Spirikhin, and I. B. Abdrakhmanov, Izv. Akad. Nauk, Ser. Khim., 1789 (2000).Google Scholar
  5. 5.
    E. Pretsch, T. Clerk, J. Seible, and W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, Berlin, Heidelberg, New York, Tokyo (1983), p. 730.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • R. R. Gataullin
    • 1
  • R. R. Ishberdina
    • 1
  • O. V. Shitikova
    • 1
  • F. F. Minnigulov
    • 1
  • L. V. Spirikhin
    • 1
  • I. B. Abdrakhmanov
    • 2
  1. 1.Institute of Organic ChemistryUfa Scientific Center of the Russian Academy of SciencesUfa
  2. 2.Bashkir State Agricultural UniversityUfaRussia

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