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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 11, pp 1390–1394 | Cite as

Signs of formation and chemical evolution of zwitterions in the reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde

  • L. V. Andriyankova
  • K. V. Belyaeva
  • L. P. Nikitina
  • A. G. Mal’kina
  • T. I. Vakul’skaya
  • S. S. Khutsishvili
  • L. M. Sinegovskaya
  • B. A. TrofimovEmail author
Article

Primary monitoring of the three-component reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde by EPR, UV, NMR, and IR spectroscopy has been carried out. Experimental evidence has been obtained for the formation of zwitterions and carbenes of the imidazole series as intermediates of a new functionalization reaction of the imidazole ring leading to 2-benzoyl-3-(1-methyl-1H-imidazol-2-yl)-3-phenylpropanenitrile.

Keywords

aldehydes carbenes cyanoacetylenes 1-substituted imidazoles zwitterions monitoring reaction multicomponent reactions nucleophilic addition 

Notes

The work was carried out with the financial support of the Russian Foundation for Fundamental Investigations (grant No. 11-03-00203a), the Grants Council of the President of the Russian Federation (NSh 3230.2010.3), the Presidium of the Russian Academy of Sciences (Program 25), and the Division of Chemistry and Materials Sciences of the Russian Academy of Sciences (No. 5.1).

References

  1. 1.
    B. A. Trofimov, L. V. Andriyankova, S. A. Zhivet’ev, A. G. Mal'kina, and V. K. Voronov, Tetrahedron Lett., 43, 1093 (2002).CrossRefGoogle Scholar
  2. 2.
    B. A. Trofimov, L. V. Andriyankova, S. I. Shaikhudinova, T. I. Kazantseva, A. G. Mal'kina, and A. V. Afonin, Synthesis, 853 (2002).Google Scholar
  3. 3.
    L. V. Andriyankova, A. G. Mal’kina, A. V. Afonin, and B. A. Trofimov, Mendeleev Commun., 13, 186 (2003).CrossRefGoogle Scholar
  4. 4.
    B. A. Trofimov, L. V. Andriyankova, R. T. Tlegenov, A. G. Mal’kina, A. V. Afonin, L. N. Il’icheva, and L. P. Nikitina, Mendeleev Commun., 15, 33 (2005).CrossRefGoogle Scholar
  5. 5.
    B. A. Trofimov, L. V. Andriyankova, A. G. Mal’kina, L. P. Nikitina, A. V. Afonin, I. A. Ushakov, L. M. Sinegovskaya, and T. I. Vakul’skaya, Eur. J. Org. Chem., 1581 (2006).Google Scholar
  6. 6.
    B. A. Trofimov, L. V. Andriyankova, A. G. Mal’kina, K. V. Belyaeva, L. P. Nikitina, O. A. Dyachenko, O. N. Kazheva, A. N. Chekhlov, G. V. Shilov, A. V. Afonin, I. A. Ushakov, and L. V. Baikalova, Eur. J. Org. Chem., 1018 (2007).Google Scholar
  7. 7.
    B. A. Trofimov, L. V. Andriyankova, A. G. Mal'kina, K. V. Belyaeva, L. P. Nikitina, and L. V. Baikalova, Mendeleev Commun., 17, 237 (2007).CrossRefGoogle Scholar
  8. 8.
    B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal’kina, L. P. Nikitina, A. V. Afonin, and I. A. Ushakov, J. Org. Chem., 73, 9155 (2008).CrossRefGoogle Scholar
  9. 9.
    B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal’kina, L. P. Nikitina, A. V. Afonin, and I. A. Ushakov, Mendeleev Commun., 19, 42 (2009).CrossRefGoogle Scholar
  10. 10.
    B. A. Trofimov, L. V. Andriyankova, L. P. Nikitina, K. V. Belyaeva, A. G. Mal’kina, and A. V. Afonin, Synthesis, 1536 (2010).Google Scholar
  11. 11.
    L. V. Andriyankova, K. V. Belyaeva, L. P. Nikitina, A. G. Mal’kina, A. V. Afonin, and B. A. Trofimov, Synthesis, 2828 (2010).Google Scholar
  12. 12.
    B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal'kina, L. P. Nikitina, A. V. Afonin, and I. A. Ushakov, Eur. J. Org. Chem., 1772 (2010).Google Scholar
  13. 13.
    B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal’kina, L. P. Nikitina, O. A. Dyachenko, O. N. Kazheva, G. G. Alexandrov, G. V. Shilov, A. V. Afonin, and I. A. Ushakov, Tetrahedron, 67, 1288 (2011).CrossRefGoogle Scholar
  14. 14.
    D. Tapu, D. A. Dixon, and C. Roe, Chem. Rev., 109, 3385 (2009).CrossRefGoogle Scholar
  15. 15.
    L. A. Kazitsyna and N. B. Kupletskaya, Application of UV, IR, and NMR Spectroscopy in Organic Chemistry [in Russian], Vysshaya Shkola, Moscow (1971), p. 216.Google Scholar
  16. 16.
    R. M. Silverstein, G. C. Basler, and T. C. Morrill, Spectrometric Identification of Organic Compounds [Russian translation], Mir, Moscow (1977), p. 198.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • L. V. Andriyankova
    • 1
  • K. V. Belyaeva
    • 1
  • L. P. Nikitina
    • 1
  • A. G. Mal’kina
    • 1
  • T. I. Vakul’skaya
    • 1
  • S. S. Khutsishvili
    • 1
  • L. M. Sinegovskaya
    • 1
  • B. A. Trofimov
    • 1
    Email author
  1. 1.A. E. Favorsky Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

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