Chemistry of Heterocyclic Compounds

, Volume 13, Issue 2, pp 190–198 | Cite as

Imidazoles in the hetarylation reaction

  • A. K. Sheinkman
  • T. V. Stupnikova
  • N. A. Klyuev
  • L. Yu. Petrovskaya
  • V. G. Zhil'nikov


Indoles and pyrrole were subjected to hetarylation with imidazole and benzimidazole in the presence of aliphatic, aromatic, and heteroaromatic carboxylic acid chlorides. The resulting N,N′-diacylimidazolinyl- and N,N′-diacylbenzimidazolinylindoles were converted to 2-(3′-indolyl)-1,3-diacylimidazolium and N,N′-diacylbenzimidazolium salts by the action of trityl perchlorate.


Chloride Organic Chemistry Imidazole Carboxylic Acid Indole 
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Literature cited

  1. 1.
    A. K. Sheinkman, V. A. Ivanov, N. A. Klyuev, and G. A. Mal'tseva, Zh. Org. Khim., 9, 2550 (1973).Google Scholar
  2. 2.
    A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 1, 3 (1974).Google Scholar
  3. 3.
    M. Khamana, Khim. Geterotsikl. Soedin., No. 9, 1155 (1973).Google Scholar
  4. 4.
    P. Wolfeden and W. Jencks, J. Am. Chem. Soc., 83, 4390 (1961).Google Scholar
  5. 5.
    O. Gerngross, Ber., 46, 4723 (1972).Google Scholar
  6. 6.
    J. Bergman, Tetrahedron Lett., No. 46, 4723 (1972).Google Scholar
  7. 7.
    T. V. Stupnikova, V. I. Sokolov, A. F. Pozharskii, and A. K.Sheinkman, Material from the Second Symposium on the Chemistry and Technology of Heterocyclic Compounds of Fossil Fuels [in Russian], Donetsk (1973), p. 49.Google Scholar
  8. 8.
    L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).Google Scholar
  9. 9.
    R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1974).Google Scholar
  10. 10.
    A. M. Duffield and E. Djerassi, Acta Chem. Scand., 22, 2329 (1968).Google Scholar
  11. 11.
    V. P. Joynt, R. R. Arndt, A. Jordaan, K. Biemann, and J. L. Occolowitz, J. Chem. Soc., B, 980 (1966).Google Scholar
  12. 12.
    N. A. Klyuev, R. A. Khmel'nitskii, G. A. Mal'tseva, A. K. Sheinkman, V. A. Ivanov, and B. M. Zolotarev. Khim. Geterotsikl. Soedin., No. 7, 979 (1973).Google Scholar
  13. 13.
    J. H. Bowil, R. G. Cooks, S. -O. Lawesson, and G. Schroll, Austral. J. Chem., 20, 1601 (1967).Google Scholar
  14. 14.
    A. K. Sheinkman, Yu. N. Sheinker, S. L. Portnova, and A. N. Kost, Dokl. Akad. Nauk SSSR, 157, 1416 (1964).Google Scholar
  15. 15.
    B. I. Khristich, G. M. Suvorova, and A. I. Simonov, Khim. Geterotsikl. Soedin., No. 10. 1398 (1974).Google Scholar
  16. 16.
    R. Majima and T. Shigematsu, Ber., 57, 1452 (1924).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • A. K. Sheinkman
    • 1
  • T. V. Stupnikova
    • 1
  • N. A. Klyuev
    • 1
  • L. Yu. Petrovskaya
    • 1
  • V. G. Zhil'nikov
    • 1
  1. 1.Donetsk State UniversityDonetsk

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