Skip to main content
SpringerLink
Log in

Reactions of highly electrophilic 6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines with C-nucleophiles

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

Abstract

Reactions of 2-R-6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines with indoles and 1,3-dicarbonyl compounds were studied. It was found that stable products of nucleophilic addition to the pyridine ring were formed under mild conditions in the absence of a base. The new derivatives of 1,5-dihydro[1,2,4]triazolo[1,5-a]pyridine were synthesized in up to 96% yield.

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

References

  1. F. Terrier, Chem. Rev., 1982, 82, 77; DOI: https://doi.org/10.1021/cr00048a001.

    Article  CAS  Google Scholar 

  2. E. Buncel, J. M. Dust, F. Terrier, Chem. Rev., 1995, 95, 2261; DOI: https://doi.org/10.1021/cr00039a001.

    Article  CAS  Google Scholar 

  3. F. Terrier, Modern Nucleophilic Aromatic Substitution, Wiley-VCH Verlag GmbH, 2013, 472 pp.

  4. F. Terrier, Nucleophilic Aromatic Displacement. The Influence of the Nitro Group, VCH Publishers, New York, 1991, 460 pp.

    Google Scholar 

  5. G. A. Artamkina, M. P. Egorov, I. P. Beletskaya, Chem. Rev., 1982, 82, 427; DOI: https://doi.org/10.1021/cr00050a004.

    Article  CAS  Google Scholar 

  6. E. Buncel, M. R. Crampton, M. J. Strauss, F. Terrier, Electron-Deficient Aromatic- and Heteroaromatic-Base Interactions: the Chemistry of Anion Sigma Complexes, Elsevier Science Publishers, Amsterdam—New York, 1984, 516 pp.

    Google Scholar 

  7. V. P. Ananikov, E. A. Khokhlova, M. P. Egorov, A. M. Sakharov, S. G. Zlotin, A. V. Kucherov, L. M. Kustov, M. I. Gening, N. E. Nifantiev, Mendeleev Commun., 2015, 25, 75; DOI: https://doi.org/10.1016/j.mencom.2015.03.001.

    Article  CAS  Google Scholar 

  8. M. A. Bastrakov, A. M. Starosotnikov, A. A. Pavlov, I. L. Dalinger, S. A. Shevelev, Chem. Heterocycl. Compd., 2016, 52, 690; DOI: https://doi.org/10.1007/s10593-016-1950-3.

    Article  CAS  Google Scholar 

  9. V. V. Ivanova, A. K. Fedorenko, A. M. Starosotnikov, M. A. Bastrakov, Russ. Chem. Bull., 2022, 71, 394; DOI: https://doi.org/10.1007/s11172-022-3596-x.

    Google Scholar 

  10. A. M. Starosotnikov, D. V. Shkaev, M. A. Bastrakov, I. V. Fedyanin, S. A. Shevelev, I. L. Dalinger, Mendeleev Commun., 2018, 28, 638; DOI: https://doi.org/10.1016/j.mencom.2018.11.025.

    Article  CAS  Google Scholar 

  11. A. M. Strarosotnikov, D. V. Shkaev, M. A. Bastrakov, I. V. Fedyanin, S. A. Shevelev, I. L. Dalinger, Beilstein J. Org. Chem., 2017, 13, 2854; DOI: https://doi.org/10.3762/bjoc.13.277.

    Article  Google Scholar 

  12. K. Kubo, N. Ito, I. Souzo, Y. Isomura, H. Homma, M. Murakami, Nitrogen-containing Heterocyclic Compounds, G. B. Pat. 1, 588, 166, April 15, 1981.

  13. A. K. Sadana, Y. Mirza, K. R. Aneja, O. Prakash, Eur. J. Med. Chem., 2003, 38, 533; DOI: https://doi.org/10.1016/s0223-5234(03)00061-8.

    Article  CAS  PubMed  Google Scholar 

  14. Q. Ye, W. Mao, Y. Zhou, L. Xu, Q. Li, Y. Gao, J. Wang, C. Li, Y. Xu, Y. Xu, H. Liao, L. Zhang, J. Gao, J. Li, T. Pang, Bioorg. Med. Chem., 2015, 23, 1179; DOI: https://doi.org/10.1016/j.bmc.2014.12.026.

    Article  CAS  PubMed  Google Scholar 

  15. K. Chun, J.-S. Park, H.-C. Lee, Y.-H. Kim, I.-H. Ye, K.-J. Kim, I.-W. Ku, M.-Y. Noh, G.-W. Cho, H. Kim, S. H. Kim, J. Kim, Bioorg. Med. Chem. Lett., 2013, 23, 3983; DOI: https://doi.org/10.1016/j.bmcl.2013.03.119.

    Article  CAS  PubMed  Google Scholar 

  16. T. P. Selby, Substituted Phenyltriazolopyrimidine Herbicides, Eur. Pat. 353,902, February 7, 1990.

  17. X.-H. Liu, Z.-H. Sun, M.-Y. Yang, C.-X. Tan, J.-Q. Weng, Y.-G. Zhang, Y. Ma, Chem. Biol. Drug Des., 2014, 84, 342; DOI: https://doi.org/10.1111/cbdd.12323.

    Article  CAS  PubMed  Google Scholar 

  18. A. M. Starosotnikov, M. A. Bastrakov, D. A. Knyazev, I. V. Fedyanin, V. V. Kachala, I. L. Dalinger, Chem. Select., 2019, 4, 1510; DOI: https://doi.org/10.1002/slct.201803068.

    CAS  Google Scholar 

  19. A. M. Starosotnikov, K. V. Ilkov, M. A. Bastrakov, I. V. Fedyanin, V. A. Kokorekin, Chem. Heterocycl. Compd., 2020, 56, 92; DOI: https://doi.org/10.1007/s10593-020-02628-1.

    Article  CAS  Google Scholar 

  20. G. L. Rusinov, V. L. Mikhailov, O. N. Chupakhin, Russ. Chem. Bull., 1999, 48, 1391; DOI: https://doi.org/10.1007/BF02495315.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. A. Bastrakov, V. G. Nadykta, A. K. Fedorenko & A. M. Starosotnikov

Authors
  1. M. A. Bastrakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. G. Nadykta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. K. Fedorenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. M. Starosotnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. A. Bastrakov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 960–965, April, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bastrakov, M.A., Nadykta, V.G., Fedorenko, A.K. et al. Reactions of highly electrophilic 6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines with C-nucleophiles. Russ Chem Bull 72, 960–965 (2023). https://doi.org/10.1007/s11172-023-3860-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3860-6

Key words

Search

Navigation