Skip to main content
SpringerLink
Log in

A convenient route to cyano derivatives of benzonaphthyridines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A smooth synthesis of benzo[c][1,5]naphthyridine-6-carbonitrile and benzo[h][1,6]naphthyridine-5-carbonitrile, starting from benzonaphthyridine N-oxides, is achieved by treatment with trimethylsilane carbonitrile (Me3SiCN) in CH2Cl2 at 0–5 °C. The resulting nitriles are then hydrolyzed to the corresponding acids by boiling in aqueous alkali.

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. R. A. Abramovitch and I. Shinkai, Acc. Chem. Res., 9, 192 (1976).

    Article  CAS  Google Scholar 

  2. T. Hisano, S. Yoshikawa, and K. Muraoka, Chem. Pharm. Bull., 22, 1611 (1974).

    CAS  Google Scholar 

  3. Y. Kurasawa, A. Takada, and H. S. Kim, J. Heterocycl. Chem., 32, 1085 (1995).

    Article  CAS  Google Scholar 

  4. H. S. Kim, Y. Kurasawa, C. Yoshii, M. Masuyama, A. Takada, and Y. Okamoto, J. Heterocycl. Chem., 27, 1111 (1990).

    Article  CAS  Google Scholar 

  5. B. Bachowska and T. Zujewska, Pol. J. Chem., 72, 89 (1998).

    CAS  Google Scholar 

  6. B. Bachowska and T. Zujewska, Monatsh. Chem., 132, 849 (2001).

    CAS  Google Scholar 

  7. B. Bachowska, Monatsh. Chem., 133, 1071 (2002).

    CAS  Google Scholar 

  8. E. Colvin, Silicon In Organic Synthesis, Butterworths, London, 1980.

    Google Scholar 

  9. W. P. Weber, Silicon Reagents for Organic Synthesis, Springer Verlag, Berlin, 1983.

    Google Scholar 

  10. G. A. Olah, G. K. S. Prakash, Q. Wang, X.-Y. Li, and W. C. Groutas, in: L. A. Paquette (editor), Encyclopedia of Reagents for Organic Synthesis, J. Wiley & Sons, New York, 1995, Vol. 7, p. 5165.

    Google Scholar 

  11. G. Mlostoń, M. Celeda, G. K. Surya Prakash, G. A. Olah, and H. Heimgartner, Helv. Chim. Acta, 83, 728 (2000).

    Article  Google Scholar 

  12. H. Vorbrüggen, Acc. Chem. Res., 28, 509 (1995).

    Article  Google Scholar 

  13. B. Bachowska and W. Śliwa, Monatsh. Chem., 115, 1101 (1984).

    Article  CAS  Google Scholar 

  14. B. Bachowska and W. Śliwa, Acta Chim. Hung., 125, 491 (1988).

    CAS  Google Scholar 

  15. B. Bachowska, Monatsch. Chem., 126, 227 (1995).

    Article  CAS  Google Scholar 

  16. T. Zujewska and B. Bachowska, Pol. J. Chem., 72, 2507 (1998).

    CAS  Google Scholar 

  17. B. Bachowska and T. Zujewska, Aust. J. Chem., 54, 105 (2001).

    Article  CAS  Google Scholar 

  18. W. Śliwa and J. Młochowski, Rocz. Chem., 50, 695 (1976); Chem. Abstr., 86, 55310 (1977).

  19. Y. Kobayashi, I. Kumadaki, and K. Morinaga, Chem. Pharm. Bull., 17, 1511 (1969).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Environmental Protection, and Biotechnology, Jan Długosz University, 13/15 Armii Krajowei Ave, Częstochowa, 42-200, Poland

    B. Bachowska

Authors
  1. B. Bachowska
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. Bachowska.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, 406–409, March, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bachowska, B. A convenient route to cyano derivatives of benzonaphthyridines. Chem Heterocycl Comp 47, 332–335 (2011). https://doi.org/10.1007/s10593-011-0761-9

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0761-9

Keywords

Search

Navigation