Skip to main content
SpringerLink
Log in

Reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the KOH—H2O system

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the presence of water (0—25 °C, 20 mol.% KOH, 5 equiv. H2O) is accompanied by the loss of aromaticity of the quinoline nucleus and results in double functionalization of the molecule at the nitrogen atom and the methyl group. Two 2-cyano-1-phenylethenyl groups were introduced into the molecule to form (2E,4E)-4-{1-[(Z)-2-cyano-1-phenylethenyl]quinolin-2(1H)-ylidene}-3-phenylbut-2-enenitrile in 59—67% yield. This reaction is stereoselective: the N-2-cyano-1-phenylethenyl-substituent has the Z-configuration, while the 1,3-diene moiety at the methyl group has the E,E-configuration. (2E)-3-Phenyl-4-(quinolin-2-yl)but-2-enenitrile that formed as a by-product (0—24% yields) is formally the addition product of the methyl group of the quinoline substrate at the acetylenic bond.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. Mrozek-Wilczkiewicz, E. Spaczynska, K. Malarz, W. Cieslik, M. Rams-Baron, V. Krystof, R. Musiol, PLoS One, 2015, 10, e0142678/1.

    Article  Google Scholar 

  2. S. Maddela, M. Venugopal, R. Maddela, M. Ajitha, Ind. J. Chem., Sect. B, 2015, 54B, 930.

    CAS  Google Scholar 

  3. G. B. Raju, M. Mahesh, G. Manjunath, P. V. Ramana, Chem. Sci. Trans., 2016, 5, 125.

    CAS  Google Scholar 

  4. N. S. Kumar, L. C. Rao, N. J. Babu, V. D. Kumar, U. S. N. Murthy, H. M. Meshram, Synlett, 2015, 26, 1808.

    Article  CAS  Google Scholar 

  5. V. V. Kouznetsov, C. M. Melendez Gomez, M. G. Derita, L. Svetaz, E. del Olmo, S. A. Zacchino, Bioorg. Med. Chem., 2012, 20, 6506.

    Article  CAS  Google Scholar 

  6. R. M. Cross, A. Monastyrskyi, T. S. Mutka, J. N. Burrows, D. E. Kyle, R. Manetsch, J. Med. Chem., 2010, 53, 7076.

    Article  CAS  Google Scholar 

  7. S. C. Teguh, N. Klonis, S. Duffy, L. Lucantoni, V. M. Avery, C. A. Hutton, J. B. Baell, L. Tilley, J. Med. Chem., 2013, 56, 6200.

    Article  CAS  Google Scholar 

  8. V. Radtke, Quinophthalone Pigments, in High Performance Pigments, Eds E. B. Faulkner, R. J. Schwartz, Wiley-VCH, Weinheim, 2009, 522 p.

  9. H. Berneth, Methine Dyes and Pigments, in Ullmann´s Ency-clopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008, 109 p.

    Google Scholar 

  10. M. Ya. Goikhman, L. I. Subbotina, A. A. Martynenkov, M. A. Smirnov, R. Yu. Smyslov, E. N. Popova, A. V. Yaki-manskii, Russ. Chem. Bull., 2011, 60, 295.

    Article  CAS  Google Scholar 

  11. T. N. Gavrishova, V. M. Li, K. F. Sadykova, M. F. Budyka, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 1495.

    Article  CAS  Google Scholar 

  12. Yu. A. Sayapin, N. B. Duong, E. A. Gusakov, I. V. Dorogan, V. V. Tkachev, V. S. Gorkovets, V. N. Komissarov, N. T. Duong, D. D. Nguyen, G. V. Shilov, S. M. Aldoshin, V. I. Minkin, Russ. Chem. Bull., 2016, 65, 2461.

    Article  CAS  Google Scholar 

  13. B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal´kina, L. P. Nikitina, Russ. Chem. Bull., 2008, 57, 2233.aaaa

    Article  CAS  Google Scholar 

  14. B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, Chem. Heterocycl. Compd., 2012, 48, 147 (and references therein).

    Article  CAS  Google Scholar 

  15. B. A. Trofimov, L. V. Andriyankova, L. P. Nikitina, K. V. Belyaeva, A. G. Mal´kina, L. N. Sobenina, A. V. Afonin, I. A. Ushakov, Org. Lett., 2013, 15, 2322.

    Article  CAS  Google Scholar 

  16. B. A. Trofimov, L. V. Andriyankova, L. P. Nikitina, K. V. Belyaeva, A. G. Mal´kina, I. Yu. Bagryanskaya, A. V. Afo-nin, I. A. Ushakov, Eur. J. Org. Chem., 2016, 1199.

    Google Scholar 

  17. K. V. Belyaeva, L. V. Andriyankova, L. P. Nikitina, I. Yu. Bagryanskaya, A. V. Afonin, I. A. Ushakov, A. G. Mal´kina, B. A. Trofimov, Tetrahedron, 2015, 71, 2891.

    Article  CAS  Google Scholar 

  18. B. A. Trofimov, K. V. Belyaeva, L. V. Andriyankova, L. P. Nikitina, A. G. Mal´kina, Mendeleev Commun., 2017, 27, 109.

    Article  CAS  Google Scholar 

  19. K. V. Belyaeva, A. V. Afonin, L. V. Andriyankova, O. G. Volostnykh, L. P. Nikitina, A. G. Mal´kina, I. A. Ushakov, V. I. Smirnov, L. V. Klyba, B. A. Trofimov, Mendeleev Com-mun., 2014, 24, 156.

    Article  CAS  Google Scholar 

  20. B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. G. Mal´kina, Eur. J. Org. Chem., 2015, 7876.

    Google Scholar 

  21. B. A. Trofimov, L. V. Andriyankova, A. G. Mal´kina, L. P. Nikitina, A. V. Afonin, I. A. Ushakov, L. M. Sinegovskaya, T. I. Vakul´skaya, Eur. J. Org. Chem., 2006, 1581.

    Google Scholar 

  22. B. A. Trofimov, L. V. Andriyankova, L. P. Nikitina, K. V. Belyaeva, A. G. Mal´kina, A. V. Afonin, I. A. Ushakov, Tetrahedron Lett., 2013, 54, 4693.

    Article  CAS  Google Scholar 

  23. K. V. Belyaeva, L. P. Nikitina, L. V. Andriyankova, in Khimiya geterotsiklicheskikh soedinenii. Sovremennye as-pekty [Chemistry of Heterocyclic Compounds. Modern As-pects], Ed. V. G. Kartsev, MBFNP, Moscow, 2014, 1, 91 (in Russian).

    Google Scholar 

  24. S. I. Miller, R. Tanaka, in Selective Organic Transformations, Ed. B. S. Thyagarajan, Wiley-Interscience, New York, 1970, 1, p. 143.

  25. I. Dickstein, S. I. Miller, in The Chemistry of the Carbon-Carbon Triple Bond, Part 2; Ed. S. Patai, Wiley, New York, 1978 814

  26. G. M. Sheldrick, Acta Crystallogr., 2008, D64, 112.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko & B. A. Trofimov

Authors
  1. K. V. Belyaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. P. Nikitina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Afonin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Vashchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. A. Trofimov.

Additional information

On the occasion of the 60th anniversary of A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2258–2263, December, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Belyaeva, K.V., Nikitina, L.P., Afonin, A.V. et al. Reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the KOH—H2O system. Russ Chem Bull 66, 2258–2263 (2017). https://doi.org/10.1007/s11172-017-2011-5

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-2011-5

Key words

Search

Navigation