Skip to main content
SpringerLink
Log in

(E)-6-(2-Arylvinyl)-2,2′-bipyridines: a convenient synthesis and fluorescent properties

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

Abstract

A convenient two-step synthesis of 6-(2-arylvinyl)-substituted 2,2′-bipyridines via S HN functionalization of 5-unsubstituted 1,2,4-triazines with subsequent aza-Diels-Alder reaction was proposed. The fluorescent properties of the obtained 2,2′-bipyridines were studied.

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. O. Maury, J.-P. Guegan, T. Renouard, A. Hilton, P. Dupau, N. Sandon, L. Toupet, H. Le Bozec, New J. Chem., 2001, 25, 1553; DOI: https://doi.org/10.1039/B106096C.

    Article  CAS  Google Scholar 

  2. C. Bonaccorso, A. Cesaretti, F. Elisei, L. Mencaroni, A. Spalletti, C. G. Fortuna, ChemPhysChem, 2018, 19, 1917; DOI: https://doi.org/10.1002/cphc.201800391.

    Article  CAS  Google Scholar 

  3. S. Dihua, L. Xiangjun, W. Shangrong, W. Linlin, Pat. CN 104693199 (A), 2015.

  4. L. Shuping, Y. Zhejian, C. Hao, X. Liangmin, W. Mingming, W. Qing’an, Pat. CN 106749411 (A), 2017.

  5. N.-Y. Chen, L.-M. Xia, A. J. J. Lennox, Y.-Y. Sun, H. Chen, H.-M. Jin, H. Junge, Q.-A. Wu, J.-H. Jia, M. Beller, S.-P. Luo, Chem. Eur. J., 2017, 23, 3631; DOI: https://doi.org/10.1002/chem.201602598.

    Article  CAS  Google Scholar 

  6. T. Yu, V. K.-M. Au, D. P.-K. Tsang, M.-Y. Chan, V. W.-W. Yam, Dalton Trans., 2015, 44, 18983; DOI: https://doi.org/10.1039/c5dt02920a.

    Article  CAS  Google Scholar 

  7. T. Feng, X. Li, J. Wu, C. He, C. Duan, C. Chin, Chem. Lett., 2020, 31, 95; DOI: https://doi.org/10.1016/j.cclet.2019.04.059.

    CAS  Google Scholar 

  8. K. Kodama, A. Kobayashi, T. Hirose, Tetrahedron Lett., 2013, 54, 5514; DOI: https://doi.org/10.1016/j.tetlet.2013.07.150.

    Article  CAS  Google Scholar 

  9. P. Kathirgamanathan, S. Surendrakumar, R. R. Vanga, S. Ravichandran, J. Antipan-Lara, S. Ganeshamurugan, M. Kumaraverl, G. Paramaswara, V. Arkley, Org. Electron., 2011, 12, 666; DOI: https://doi.org/10.1016/j.orgel.2010.12.025.

    Article  CAS  Google Scholar 

  10. T. N. Gavrishova, V. M. Lee, K. V. Gor’kov, M. F. Budyka, Russ. J. Appl. Chem., 2011, 84, 507; DOI: https://doi.org/10.1134/S107042721103030X.

    Article  CAS  Google Scholar 

  11. E. N. Gulakova, O. Yu. Kolosova, O. A. Fedorova, Russ. Chem. Bull., 2010, 59, 1292; DOI: https://doi.org/10.1007/s11172-010-0235-8.

    Article  CAS  Google Scholar 

  12. A. F. Khasanov, D. S. Kopchuk, I. S. Kovalev, O. S. Taniya, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Mendeleev Commun., 2015, 25, 332; DOI: https://doi.org/10.1016/j.mencom.2015.09.003.

    Article  CAS  Google Scholar 

  13. A. P. Krinochkin, D. S. Kopchuk, I. S. Kovalev, S. Santra, G. V. Zyryanov, A. Majee, V. L. Rusinov, O. N. Chupakhin, ChemistrySelect, 2020, 5, 2753; DOI: https://doi.org/10.1002/slct.202000044.

    Article  CAS  Google Scholar 

  14. I. S. Kovalev, D. S. Kopchuk, A. F. Khasanov, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, Mendeleev Commun., 2014, 24, 117; DOI: https://doi.org/10.1016/j.mencom.2014.03.018.

    Article  CAS  Google Scholar 

  15. R. F. Fatykhov, M. I. Savchuk, E. S. Starnovskaya, M. V. Bobkina, D. S. Kopchuk, E. V. Nosova, G. V. Zyryanov, I. A. Khalymbadzha, O. N. Chupakhin, V. N. Charushin, V. G. Kartsev, Mendeleev Commun., 2019, 29, 299; DOI: https://doi.org/10.1016/j.mencom.2019.05.019.

    Article  CAS  Google Scholar 

  16. D. N. Kozhevnikov, V. N. Kozhevnikov, A. M. Prokhorov, M. M. Ustinova, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov, B. König, Tetrahedron Lett., 2006, 47, 869; DOI: https://doi.org/10.1016/j.tetlet.2005.12.006.

    Article  CAS  Google Scholar 

  17. Y. K. Shtaitz, M. I. Savchuk, E. S. Starnovskaya, A. P. Krinochkin, D. S. Kopchuk, S. Santra, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, AIP Conf. Proc., 2019, 2063, 040050; DOI: https://doi.org/10.1063/1.5087382.

    Article  Google Scholar 

  18. V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. König, D. N. Kozhevnikov, Tetrahedron, 2008, 64, 8963; DOI: https://doi.org/10.1016/j.tet.2008.06.040.

    Article  CAS  Google Scholar 

  19. D. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, P. A. Slepukhin, V. N. Kozhevnikov, Tetrahedron Lett., 2006, 47, 7025; DOI: https://doi.org/10.1016/j.tetlet.2006.07.111.

    Article  CAS  Google Scholar 

  20. A. Pandey, R. Rai, M. Pal, S. Pandey, Phys. Chem. Chem. Phys., 2014, 16, 1559; DOI: https://doi.org/10.1039/C3CP53456A.

    Article  CAS  Google Scholar 

  21. E. C. Constable, M. Neuburger, P. Rösel, G. E. Schneider, J. A. Zampese, C. E. Housecroft, F. Monti, N. Armaroli, R. D. Costa, E. Ortí, Inorg. Chem., 2013, 52, 885; DOI: https://doi.org/10.1021/ic302026f.

    Article  CAS  Google Scholar 

  22. D. A. Samarkina, D. R. Gabdrakhmanov, V. E. Semenov, F. G. Valeeva, A. E. Nikolaev, L. F. Saifina, L. Ya. Zakharova, Russ. J. Gen. Chem., 2017, 87, 1977; DOI: https://doi.org/10.1134/S1070363217090134.

    Article  CAS  Google Scholar 

  23. T. A. Dar, A. S. Bulbula, M. Sankar, K. M. J. Kadish, Porphyrins Phthalocyanines, 2020, 24, 985; DOI: https://doi.org/10.1142/S108842462050008X.

    Article  CAS  Google Scholar 

  24. L. Porrès, A. Holland, L.-O. Pålsson, A. P. Monkman, C. Kemp, A. Beeby, J. Fluoresc., 2006, 16, 267; DOI: https://doi.org/10.1007/s10895-005-0054-8.

    Article  Google Scholar 

  25. L. Rocard, A. Berezin, F. De Leo, D. Bonifazi, Angew. Chem., Int. Ed. Engl., 2015, 54, 5739; DOI: https://doi.org/10.1002/anie.201507186.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    A. F. Khasanov, D. S. Kopchuk, I. L. Nikonov, O. S. Taniya, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov & O. N. Chupakhin

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108, Ekaterinburg, Russian Federation

    A. F. Khasanov, D. S. Kopchuk, I. L. Nikonov, O. S. Taniya, G. V. Zyryanov, V. L. Rusinov & O. N. Chupakhin

Authors
  1. A. F. Khasanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. S. Kopchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. L. Nikonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. S. Taniya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. S. Kovalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. V. Zyryanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. L. Nikonov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 999–1001, May, 2021.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-10144) and the President of the Russian Federation Council for Grants for State Support of Leading Scientific Schools of the Russian Federation (Grant NSh-2700.2020.3).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khasanov, A.F., Kopchuk, D.S., Nikonov, I.L. et al. (E)-6-(2-Arylvinyl)-2,2′-bipyridines: a convenient synthesis and fluorescent properties. Russ Chem Bull 70, 999–1001 (2021). https://doi.org/10.1007/s11172-021-3179-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3179-2

Key words

Search

Navigation