Skip to main content
SpringerLink
Log in

New approaches to the synthesis of 2-(trifluoromethyl)indole and 2-amino-3-(trifluoromethyl)quinoline

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New synthetic approaches to the preparation of 2-(trifluoromethyl)indole and 2-amino-3-(trifluoromethyl)quinoline have been developed. In both cases, conditions of the Leimgruber-Batcho synthesis of indoles were used in the key step.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. R. J. Sundberg, Indoles, Academic Press, London, 1996.

    Google Scholar 

  2. M. Hudlicky, A. E. Pavlath, Chemistry of Organic Fluorine Compounds II, American Chemical Society, Washington, DC, 1995

    Google Scholar 

  3. I. Ojima, J.R. McCarthy, J.T. Welch, Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series, vol. 639, Washington, 1996.

  4. Y. Girard, J. Atkinson, G. Joseph, P. Belanger, J. Fuentes, J. Rokach, S. Rooney, D. Remy, C. Hunt, J. Org. Chem., 1983, 48, 3220.

    Article  CAS  Google Scholar 

  5. Q.-Y. Chen, Z.-T. Li, J. Chem. Soc., Perkin Trans. 1, 1993, 645.

  6. W. Y. Huang, J. Fluorine Chem., 1992, 58, 1.

    Article  CAS  Google Scholar 

  7. M. Yoshida, T. Yoshida, M. Kobayashi, N. Kamigata, J. Chem. Soc., Perkin Trans. 1, 1989, 909.

  8. W. Sawada, M. Yoshida, H. Hagii, K. Aoyama, M. Kobayashi, Bull. Chem. Soc. Jpn, 1986, 59, 215.

    Article  CAS  Google Scholar 

  9. K. Miyashita, K. Kondoh, K. Tsuchiya, H. Miyabe, T. Imanishi, J. Chem. Soc., Perkin Trans. 1, 1996, 1261.

  10. M. Kobayashi, K. Sadamune, H. Mizukami, K. Uneyama, J. Org. Chem., 1994, 59, 1909.

    Article  CAS  Google Scholar 

  11. T. Konno, J. Chae, T. Ishihara, H. Yamanaka, J. Org. Chem., 2004, 69, 8258.

    Article  CAS  Google Scholar 

  12. K. E. Henegar, D. A. Hunt, Heterocycles, 1996, 42, 1471.

    Google Scholar 

  13. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, E. S. Balenkova, Tetrahedron, 2000, 56, 6557.

    Article  CAS  Google Scholar 

  14. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, E. S. Balenkova, Synthesis, 2001, 2081.

  15. A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2001, 1334 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1401].

    Google Scholar 

  16. A. V. Shastin, V. N. Korotchenko, G. N. Varseev, V. G. Nenajdenko, E. S. Balenkova, Zh. Org. Khim., 2003, 39, 433 [Russ. J. Org. Chem., 2003, 39, 427 (Engl. Transl.)].

    Google Scholar 

  17. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, E. S. Balenkova, Org. Biomol. Chem., 2003, 1, 1906.

    Article  CAS  Google Scholar 

  18. V. G. Nenajdenko, A. V. Shastin, V. N. Korotchenko, G. N. Varseev, E. S. Balenkova, Eur. J. Org. Chem., 2003, 302.

  19. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, E. S. Balenkova, Tetrahedron, 2001, 57, 7519.

    Article  CAS  Google Scholar 

  20. V. G. Nenajdenko, G. N. Varseev, V. N. Korotchenko, A. V. Shastin, E. S. Balenkova, J. Fluorine Chem., 2003, 124, 115.

    Article  CAS  Google Scholar 

  21. V. G. Nenajdenko, G. N. Varseev, V. N. Korotchenko, A. V. Shastin, E. S. Balenkova, J. Fluorine Chem., 2004, 125, 1339.

    Article  CAS  Google Scholar 

  22. V. G. Nenajdenko, G. N. Varseev, A. V. Shastin, E. S. Balenkova, J. Fluorine Chem., 2005, 126, 907.

    Article  CAS  Google Scholar 

  23. V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, E. S. Balenkova, Tetrahedron, 2001, 57, 7519.

    Article  CAS  Google Scholar 

  24. A. V. Shastin, V. M. Muzalevsky, E. S. Balenkova, V. G. Nenajdenko, Mendeleev Communications, 2006, 16, 179.

    Article  Google Scholar 

  25. V. G. Nenajdenko, V. M. Muzalevskiy, A. V. Shastin, E. S. Balenkova, G. Haufe, J. Fluorine Chem., 2007, 128, 818.

    Article  CAS  Google Scholar 

  26. V. M. Muzalevskiy, A. V. Shastin, E. S. Balenkova, V. G. Nenajdenko, Izv. Akad. Nauk, Ser. Khim., 2007, 1469 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1526].

    Google Scholar 

  27. A. D. Batcho, W. Leimgruber, U.S. Pat. 3,976,639, 1976; Chem. Abstr., 1977, 86, 29624.

    Google Scholar 

  28. P. E. Hansen, Progr. Nucl. Magn. Reson. Spect., 1981, 14, 175.

    Article  CAS  Google Scholar 

  29. L.-H. Zhou, S.-J. Tu, D.-Q. Shi, G.-Y. Dai, W.-X. Chen, Synthesis, 1998, 851.

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119992, Moscow, Russian Federation

    V. M. Muzalevskiy, E. S. Balenkova & V. G. Nenajdenko

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka Moscow Region, Russian Federation

    A. V. Shastin

  3. Institute of Organic Chemistry, Münster University, D-48149, Münster, Germany

    G. Haufe

Authors
  1. V. M. Muzalevskiy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Shastin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. S. Balenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. Haufe
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. G. Nenajdenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Shastin.

Additional information

Dedicated to Academician B. A. Trofimov in honor of his 70th anniversary.

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, D-48149 Münster, Germany.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2175–2177, October, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Muzalevskiy, V.M., Shastin, A.V., Balenkova, E.S. et al. New approaches to the synthesis of 2-(trifluoromethyl)indole and 2-amino-3-(trifluoromethyl)quinoline. Russ Chem Bull 57, 2217–2219 (2008). https://doi.org/10.1007/s11172-008-0306-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-008-0306-2

Key words

Search

Navigation