Skip to main content
Log in

Chelate synthesis of 1,6-naphthyridin-4-ones

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

Abstract

An efficient synthesis of novel functionalized 1,6-naphthyridin-4-ones is based on cyclization of difluoroboron chelate complexes of 1-alkyl-N′-benzoyl-2-methyl-4-oxo-1,4-dihydro-pyridine-3-carboximidamide under the action of dimethylformamide dimethyl acetal or sodium alkoxide.

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.

Similar content being viewed by others

References

  1. D. Bouzard, P. DiCesare, M. Essiz, J. P. Jacquet, B. Ledoussal, P. Remuzon, R. E. Kessler, J. Fung Tomc, J. Med. Chem., 1992, 35, 518; DOI: https://doi.org/10.1021/jm00081a013.

    Article  CAS  Google Scholar 

  2. G. R. Rao, K. Mogilaiah, B. Sreenivasulu, Indian J. Chem., 1996, 35B, 339.

    CAS  Google Scholar 

  3. E. Laxminarayana, T. Karunakar, S. S. Shankar, M. T. Chary, J. Adv. Drug Res., 2012, 2, 6.

    CAS  Google Scholar 

  4. T. Aboul-Fadl, F. A. S. Bin-Jubair, O. Aboul-Wafa, Eur. J. Med. Chem., 2010, 45, 4578; DOI: https://doi.org/10.1016/j.ejmech.2010.07.020.

    Article  CAS  Google Scholar 

  5. S. X. Zhang, K. F. Bastow, Y. Tachibana, S. C. Kuo, E. Hamel, A. Mauger, V. L. Narayanan, K. H. Lee, J. Med. Chem., 1999, 42, 4081; DOI: https://doi.org/10.1021/jm990208z.

    Article  CAS  Google Scholar 

  6. A. A. Fadda, A. M. El-Defrawy, S. A. El-Habiby, Am. J. Org. Chem., 2012, 2, 87.

    Article  CAS  Google Scholar 

  7. G. Roma, G. Grossi, M. DiBraccio, D. Piras, V. Ballabeni, M. Tognolini, S. Bertoni, E. Barocelli, Eur. J. Med. Chem., 2008, 43, 1665; DOI: https://doi.org/10.1016/j.ejmech.2007.10.010.

    Article  CAS  Google Scholar 

  8. P. L. Ferrarini, C. Mori, N. Tellini, Farmaco, 1990, 45, 385.

    CAS  PubMed  Google Scholar 

  9. S.-C. Kuo, S.-Y. Tsai, H.-T. Li, C.-H. Wu, K. Ishii, H. Nakamura, Chem. Pharm. Bull., 1988, 36, 4403; DOI: https://doi.org/10.1248/cpb.36.4403.

    Article  CAS  Google Scholar 

  10. V. Massari, D. Daelemans, M. L. Barreca, J. Med. Chem., 2010, 53, 641; DOI: https://doi.org/10.1021/jm901211d.

    Article  CAS  Google Scholar 

  11. V. P. Litvinov, Adv. Heterocycl. Chem., 2006, 91, 222.

    Google Scholar 

  12. T. Suresh, R. N. Kumar, P. S. Mohan, Asian J. Chem., 2003, 15, 855.

    CAS  Google Scholar 

  13. A. L. Ruchelman, S. K. Singh, A. W. X. H. Ray, Y.-M. Yang, T.-K. Li, A. Lin, L. F. Lin, E. J. LaVoie, Bioorg. Med. Chem., 2003, 11, 2061; DOI: https://doi.org/10.1016/S0968-0896(03)00051-8.

    Article  CAS  Google Scholar 

  14. V. A. Dorokhov, M. F. Gordeev, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 2638; DOI: https://doi.org/10.1007/BF00962473.

    Article  Google Scholar 

  15. L. S. Vasil’ev, F. E. Surzhikov, S. V. Baranin, V. A. Dorokhov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 1255; DOI: https://doi.org/10.1007/s11172-013-0173-3.

    Article  Google Scholar 

  16. L. S. Vasil’ev, S. V. Baranin, I. V. Zavarzin, Russ. Chem. Bull. (Int. Ed.), 2017, 66, 1398; DOI: https://doi.org/10.1007/s11172-017-1901-x.

    Article  Google Scholar 

  17. M. A. Prezent, S. V. Baranin, Yu. N. Bubnov, Russ. Chem. Bull. (Int. Ed.), 2021, 70, 763.

    Article  Google Scholar 

  18. Kh. S. Shikhaliev, A. Yu. Potapov, E. L. Polukhin, A. I. Slivkin, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 1996; DOI: https://doi.org/10.1007/s11172-009-0273-2.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. V. Baranin.

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. 1006–1009, May, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Present, M.A., Baranin, S.V. & Bubnov, Y.N. Chelate synthesis of 1,6-naphthyridin-4-ones. Russ Chem Bull 70, 1006–1009 (2021). https://doi.org/10.1007/s11172-021-3181-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3181-8

Key words

Navigation