Skip to main content
SpringerLink
Log in

Reactions of Cinnoline, Cinnoline N-Oxides, and Their Chloro Derivatives with Alkylamines: the First Case of Nucleophilic Substitution of Hydrogen in the Cinnoline Series

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In contrast to cinnoline and cinnoline N(1)-oxide, cinnoline N(2)-oxide reacts with primary and secondary amines on prolonged heating or in the presence of oxidants to give 3-alkylaminocinnolines.

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. A. V. Gulevskaya,D. V. Besedin, andA. F. Pozharskii, Izvest. Akad. Nauk, Ser. Khim., 6, 1161 (1999).

    Google Scholar 

  2. D. V. Besedin,A. V. Gulevskaya, andA. F Pozharskii, Mendeleev. Commun., 150 (2000).

  3. A. V. Gulevskaya,D. V. Besedin,A. F. Pozharskii, andZ. A. Starikova, Tetrahedron Lett., 42, 5981 (2001).

    Google Scholar 

  4. M. Ogata,H. Kano, andK. Tori, Chem. Pharm. Bull., 10, 1123 (1962).

    Google Scholar 

  5. I. Suzuki,M. Nakadate,T. Nakshimi, andN. Nagasawa, Tetrahedron Lett., 25, 2899 (1966).

    Google Scholar 

  6. O. N. Chupatkin,V. N. Charushin andH. C. Van der Plas, Nucleophllic Aromatic Substitution of Hydrogen. Acad. Press., New York, 1994.

    Google Scholar 

  7. A. O. Pozharskii andA. V Gulevskaya, Khim. Getrotsikl. Soedin., 1611 (2001).

  8. H. Van der Plas, Khim. Getrotsikl. Soedin., 1011 (1987).

  9. H. Van der Plas andM. Wozniak, Croat. Chem. Acta, 59, 33 (1986) (Engl. Trans.)

    Google Scholar 

  10. A. F. Pozharskii,A. M. Simonov, andV. N. Doron'kin, Usp. Khim., 47, 1933 (1978).

    Google Scholar 

  11. M. F. Budyka,N. B. Terent'ev, andA. N. Kost, Khim. Geterotsikl. Soedin., 11, 1554 (1977).

    Google Scholar 

  12. A. R. Katritzky andA. F. Pozharskii, Handbook of Heterocyclic Chemistry, 2nd Ed., Elsevier, Amsterdam, 2000.

    Google Scholar 

  13. J. A. Zoltewicz andL. S. Helmick, J. Am. Chem. Soc., 94, 682 (1987).

    Google Scholar 

  14. I. Hiroshi,T. Tahashi,N. Toshiko, andO. Genzo, Chem. Pharm. Bull., 18, 1497 (1970).

    Google Scholar 

  15. A. Rykowski andH. C. Van der Plas, Synthesis, 9, 884 (1985).

    Google Scholar 

  16. D. Bhattacharjee andF. D. Popp, J. Heterocycl. Chem., 17, 121 (1980).

    Google Scholar 

  17. R. N. Castle,D. B. Cox, andJ. F. Suttle, J. Am. Pharmac. Assoc. Scient. Ed., 48, 135 (1959).

    Google Scholar 

  18. I. Suzuki andT. Nakashima, Chem. Pharm. Bull., 12, 619 (1964).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Rostov State University, Rostov-on-Don, 344090, Russia

    N. A. Buluchevskaya, A. V. Gulevskaya & A. F. Pozharskii

Authors
  1. N. A. Buluchevskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Gulevskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. F. Pozharskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buluchevskaya, N.A., Gulevskaya, A.V. & Pozharskii, A.F. Reactions of Cinnoline, Cinnoline N-Oxides, and Their Chloro Derivatives with Alkylamines: the First Case of Nucleophilic Substitution of Hydrogen in the Cinnoline Series. Chemistry of Heterocyclic Compounds 39, 87–95 (2003). https://doi.org/10.1023/A:1023076810168

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1023076810168

Search

Navigation