Skip to main content
Log in

Reactions of quinoline-2(6,8)-carbaldehydes with arenes by the action of various Brønsted or Lewis acids: synthesis of diarylmethylquinolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reactions of quinoline-2(6,8)-carbaldehydes with arenes by the action of strong Brønsted (H2SO4, CF3SO3H) or Lewis (AlCl3, AlBr3) acids led to the formation of substituted diarylmethylquinolines in high yields.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1.

Similar content being viewed by others

References

  1. Achan, J.; Talisuna, A. O.; Erhart, A.; Yeka, A.; Tibenderana, J. K.; Baliraine, F. N.; Rosenthal, P. J.; D’Alessandro, U. Malar. J. 2011, 10, 144.

    Article  CAS  Google Scholar 

  2. Samosorn, S.; Bremner, J. B.; Ball, A.; Lewis, K. Bioorg. Med. Chem. 2006, 14, 857.

    Article  CAS  Google Scholar 

  3. Maignan, S.; Guilloteau, J.; Zhou-Liu, Q.; Clement-Mella, C.; Mikol, V. J. Mol. Biol. 1998, 282, 359.

    Article  CAS  Google Scholar 

  4. Zouhiri, F.; Desmaele, D.; d’Angelo, J.; Ourevitch, M.; Mouscadet, J.-F.; Leh, H.; Le Bret, M. Tetrahedron Lett. 2001, 42, 8189.

  5. McCormick, J. L.; McKee, T. C.; Cardellina II, J. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 469.

    Article  CAS  Google Scholar 

  6. Yadav, D. K.; Rai, R.; Kumar, N.; Singh, S.; Misra, S.; Sharma, P.; Shaw, P.; Perez-Sanchez, H.; Mancera, R. L.; Choi, E. H.; Kim, M.-h.; Pratap, R. Sci. Rep. 2016, 6, article number 38128.

  7. Matsuno, K.; Masuda, Y.; Uehara, Y.; Sato, H.; Muroya, A.; Takahashi, O.; Yokotagawa, T.; Furuya, T.; Okawara, T.; Otsuka, M.; Ogo, N.; Ashizawa, T.; Oshita, C.; Tai, S.; Ishii, H.; Akiyama, Y.; Asai, A. ACS Med. Chem. Lett. 2010, 1, 371.

    Article  CAS  Google Scholar 

  8. Aly, R. M.; Serya, R. A. T.; El-Motwally, A. M.; Esmat, A.; Abbas, S.; El Ella, D. A. A. Bioorg. Chem. 2017, 75, 368.

  9. Khusnutdinov, R. I.; Bayguzina, A. R.; Dzhemilev, U. M. J. Organomet. Chem. 2014, 768, 75.

    Article  CAS  Google Scholar 

  10. Madapa, S.; Tusi, Z.; Batra, S. Curr. Org. Chem. 2008, 12, 1116.

    Article  CAS  Google Scholar 

  11. Ryabukhin, D. S.; Vasilyev, A. V. Russ. Chem. Rev. 2016, 85, 637.

    Article  CAS  Google Scholar 

  12. Njoroge, M.; Njuguna, N. M.; Mutai, P.; Ongarora, D. S. B.; Smith, P. W.; Chibale, K. Chem. Rev. 2014, 114, 11138.

    Article  CAS  Google Scholar 

  13. Teixeira, C.; Vale, N.; Perez, B.; Gomes, A.; Gomes, J. R. B.; Gomes, P. Chem. Rev. 2014, 114, 11164.

    Article  CAS  Google Scholar 

  14. Barnett, D. S.; Guy, R. K. Chem. Rev. 2014, 114, 11221.

    Article  CAS  Google Scholar 

  15. Ryabukhin, D. S.; Zakusilo, D. N.; Kompanets, M. O.; Tarakanov, A. A.; Boyarskaya, I. A.; Artamonova, T. O.; Khohodorkovskiy, M. A.; Opeida, I. O.; Vasilyev, A. V. Beilstein J. Org. Chem. 2016, 12, 2125.

    Article  CAS  Google Scholar 

  16. Klumpp, D. A.; Lau, S. J. Org. Chem. 1999, 64, 7309.

    Article  CAS  Google Scholar 

  17. Prakash, G. K. S.; Paknia, F.; Chacko, S.; Mathew, T.; Olah, G. A. Heterocycles 2008, 76, 783.

    Article  CAS  Google Scholar 

  18. Sheets, M. R.; Li, A.; Bower, E. A.; Weigel, A. R.; Abbott, M. P.; Gallo, R. M.; Mitton, A. A.; Klumpp, D. A. J. Org. Chem. 2009, 74, 2502.

    Article  CAS  Google Scholar 

  19. Ryabukhin, D. S.; Turdakov, A. N.; Soldatova, N. S.; Kompanets, M. O.; Ivanov, A. Yu.; Boyarskaya, I. A.; Vasilyev, A. V. Beilstein J. Org. Chem. 2019, 15, 1962.

    Article  CAS  Google Scholar 

  20. Klumpp, D. A.; Kindelin, P. J.; Li, A. Tetrahedron Lett. 2005, 46, 2931.

    Article  CAS  Google Scholar 

  21. Gurskaya, L. Y.; Belyanskaya, D. S.; Ryabukhin, D. S.; Nilov, D. I.; Boyarskaya, I. A.; Vasilyev, A. V. Beilstein J. Org. Chem. 2016, 12, 950.

    Article  CAS  Google Scholar 

  22. Klumpp, D. A.; Jones, A.; Lau, S.; de Leon, S.; Garza, M. Synthesis 2000, 1117.

Download references

This work was supported by the Russian Foundation for Basic Research (grant 20-03-00074).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Aleksander V. Vasilyev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 964–967

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Borisova, M.А., Ryabukhin, D.S. & Vasilyev, A.V. Reactions of quinoline-2(6,8)-carbaldehydes with arenes by the action of various Brønsted or Lewis acids: synthesis of diarylmethylquinolines. Chem Heterocycl Comp 56, 964–967 (2020). https://doi.org/10.1007/s10593-020-02759-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02759-5

Keywords

Navigation