Skip to main content
SpringerLink
Log in

Novel Derivatives of Adamantyl-substituted Quinolin-6-amines and Synthesis of Imidazo[4,5-f]quinolines Therefrom

  • Short Communications
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

N-(Adamantan-1-yl)alkyl-substituted 5-nitrosoquinolin-6-amines were synthesized for the first time by the amination of 5-nitrosoquinolin-6-ol with primary N-[(adamantan-1-yl)alkyl]amines. The resulting nitrosoquinolinamines were reduced with hydrazine hydrate over Pd/C to N6-[(adamantan-1-yl)alkyl]quinoline-5,6-diamines. The latter were heated in formic acid to obtain previously unknown 3-[(adamantan-1-yl)alkyl]-3H-imidazo[4,5-f]quinolines.

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. Vodela, S., Chakravarthula, V., J. Drug Deliv. Ther., 2016, vol. 6, p. 6. doi https://doi.org/10.22270/jddt.v6i5.1278

    CAS  Google Scholar 

  2. El-Sherbeny, M.A., Maarouf, A.R., Hassan, A.H.E., and Abdel-Aziz, N.I., J. Am. Sci., 2012, vol. 8, p. 785. doi https://doi.org/10.7537/marsjas081212.110

    Google Scholar 

  3. Bagrii, E.V., Adamantany: poluchenie, svoistva, primenenie (Adamantanes: Production, Properties, Application), Moscow: Nauka, 1989.

    Google Scholar 

  4. Grigorova, O.K., Averin, A.D., Abel, A.S., Maloshitskaya, O.A., Kovalev, V.V., Beletskaya, I.P., Savelev, E.N., Orlinson, B.S., and Novakov, I.A., Russ. J. Org. Chem., 2012, vol. 48, p. 1391. doi https://doi.org/10.1134/S1070428012110012

    Article  CAS  Google Scholar 

  5. Semichenko, E.S., Gomonova, A.L., Gavrilova, N.A., and Suboch, G.A., Russ. J. Org. Chem., 2008, vol. 44, p. 647. doi https://doi.org/10.1134/S1070428008050023

    Article  CAS  Google Scholar 

  6. Gavrilova, N.A., Semichenko, E.S., Kondrasenko, A.A., and Suboch, G.A., Russ. J. Org. Chem., 2016, vol. 52, p. 368. doi https://doi.org/10.1134/S107042801603012X

    Article  CAS  Google Scholar 

  7. Frolenko, T.A., Gavrilova, N.A., Semichenko, E.S., and Suboch, G.A., Russ. J. Org. Chem., 2010, vol. 46, p. 777. doi https://doi.org/10.1134/S1070428010050349

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Reshetnev Siberian State University of Science and Technology, Pr. im. gazety Krasnoyarskii rabochii 31, Krasnoyarsk, 660037, Russia

    A. A. Abramov, M. V. Kulagina, N. A. Gavrilova, E. S. Semichenko & G. A. Suboch

  2. Institute of Chemistry and Chemical Technology, Krasnoyarsk Research Center, Siberian Branch, Russian Academy of Sciences Akademgorodok, 50, Stroenie 24, Krasnoyarsk, 660036, Russia

    A. A. Kondrasenko

  3. Kirenskii Institute of Physics, Krasnoyarsk Research Center, Siberian Branch, Russian Academy of Sciences, Akademgorodok 50, Stroenie 38, Krasnoyarsk, 660036, Russia

    A. A. Kondrasenko

Authors
  1. A. A. Abramov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Kulagina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. A. Gavrilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. S. Semichenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Kondrasenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. A. Suboch
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. S. Semichenko.

Additional information

Conflict of Interest

The authors declare no conflict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 8, pp. 1291–1295.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Abramov, A.A., Kulagina, M.V., Gavrilova, N.A. et al. Novel Derivatives of Adamantyl-substituted Quinolin-6-amines and Synthesis of Imidazo[4,5-f]quinolines Therefrom. Russ J Org Chem 55, 1234–1237 (2019). https://doi.org/10.1134/S1070428019080256

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019080256

Keywords

Search

Navigation