Skip to main content
SpringerLink
Log in

Synthesis of benzo[f]quinoline derivatives by three-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde

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

Abstract

New derivatives of benzo[f]furo[3,4-b]quinoline, spiro[benzo[f]quinoline-2,3′-furan], and benzo[f]-quinoline-2-carboxylic acid were synthesized with high selectivity by three-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde.

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. Kozlov, N.S., 5,6-Benzokhinoliny (5,6-Benzoquinolines), Minsk: Nauka i Tekhnika, 1979, p. 99.

    Google Scholar 

  2. Albert, A., Rubbo, S., and Burlrill, M., Brit. J. Exp. Path., 1949, vol. 30, p. 159.

    CAS  Google Scholar 

  3. Kuleshov, V.I., Kozlov, N.S., Libman, N.M., Kosmacheva, I.M., and Zhikhareva, O.D., Biokhimiya, 1981, vol. 46, p. 1764.

    CAS  Google Scholar 

  4. Smith, E.C., McQuaid, L.A., Goode, R.L., McNulty, A.M., Neubauer, B.L., Rocco, V.P., and Audia, J.E., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 395.

    Article  CAS  Google Scholar 

  5. Monge, A., Alvarez, E., San Martin, C., Nadal, E., Ruiz, I., Font, M., Martinez-Irujo, J.J., Santiago, E., Prieto, I., Lasarte, J.J., Sarobe, P., and Borras, F., Drug Des. Discovery, 1997, vol. 14, p. 291.

    CAS  Google Scholar 

  6. Cymerman, C.J., Torkelson, S.M., Findell, P.R., and Weiner, R.I., J. Med. Chem., 1989, vol. 32, p. 961.

    Article  Google Scholar 

  7. Effenberger, F. and Syed, J., Tetrahedron: Asymmetry, 1998, vol. 9, p. 817.

    Article  CAS  Google Scholar 

  8. Zografos, A.L. and Georgiadis, D., Synthesis, 2006, p. 3157.

  9. Jurd, L., J. Heterocycl. Chem., 1996, vol. 33, p. 1227.

    Article  CAS  Google Scholar 

  10. Atsuo, B., Tsuneo, O., Shigehisa, T., Kohei, N., Atsushi, N., Haruhiko, M., and Takashi, S., Chem. Pharm. Bull., 1999, vol. 47, p. 369.

    Google Scholar 

  11. Skrastin’sh, I.P., Vitolin’ya, R.O., Kastron, V.V., Avakumova, G.M., and Dubur, G.Ya., Khim.-Farm. Zh., 1992, no. 5, p. 43.

  12. Rose, U., Arzneim, Forsch., 1991, vol. 41, p. 199.

    CAS  Google Scholar 

  13. Iida, A., Kano, M., Kubota, Y., Koga, K., and Tomioka, K., Bioorg. Med. Chem. Lett., 1997, vol. 20, p. 2565.

    Article  Google Scholar 

  14. Kadutski, A.P., Kozlov, N.G., and Tkachev, A.V., Book of Abstracts of the 2nd Int. Conf. on Natural Products and Physiologically Active Substances/3rd EuroAsian Heterocyclic Meeting “Heterocycles in Organic and Combinatorial Chemistry,” Novosibirsk, 2004, p. 157.

  15. Kadutskii, A.P. and Kozlov, N.G., Russ. J. Org. Chem., 2006, vol. 42, p. 748.

    Article  CAS  Google Scholar 

  16. Bühler, C.A. and Pearson, D.E., Survey of Organic Syntheses, New York: Wiley, 1970, vol. 1. Translated under the title Organicheskie sintezy, Moscow: Mir, 1973, vol. 1, p. 529.

    Google Scholar 

  17. Kozlov, N.G., Pashkovskii, F.S., Tereshko, A.B., Lokot’, I.P., Gusak, K.N., and Lakhvich, F.A., Russ. J. Org. Chem., 2003, vol. 39, p. 115.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    A. P. Kadutskii & N. G. Kozlov

  2. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141, Belarus

    F. S. Pashkovskii

Authors
  1. A. P. Kadutskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. G. Kozlov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. S. Pashkovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. P. Kadutskii.

Additional information

Original Russian Text © A.P. Kadutskii, N.G. Kozlov, F.S. Pashkovskii, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 410–415.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kadutskii, A.P., Kozlov, N.G. & Pashkovskii, F.S. Synthesis of benzo[f]quinoline derivatives by three-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde. Russ J Org Chem 45, 399–403 (2009). https://doi.org/10.1134/S1070428009030087

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009030087

Keywords

Search

Navigation