Skip to main content
SpringerLink
Log in

2-(Fur-2-yl)thiazolo[4,5-f]quinoline: Synthesis and Electrophilic Substitution Reactions

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

Abstract

Condensation of quinoline-5-amine with furan-2-carbonyl chloride in propan-2-ol afforded N-(5- quinolyl)furan-2-carboxamide, treatment of which with an excess of P2S5 in anhydrous pyridine led to the formation of the corresponding thioamide. Oxidation of the latter with potassium ferricyanide in an alkaline medium furnished 2-(fur-2-yl)thiazolo[4,5-f]quinoline. A plausible mechanism for its formation was proposed. The reactions of electrophilic substitution (nitration, bromination, formylation, acylation) of the obtained N-(5-quinolyl)furan-2-carboxamide were studied.

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. Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Heterocycles in Life and Society, Chichester: J. Wiley & Sons, 1997.

    Google Scholar 

  2. Roshal, A.D., Lukianov, B.S., and El’chaninov, M.M., Russ. J. Phys. Chem. (А), 2003, vol. 77, no. 10, p. 1709.

    Google Scholar 

  3. Jacobson, P., Ber., 1886, vol. 19, pp. 1067, 1811.

    Article  Google Scholar 

  4. Fărcăşan, V. and Makkay, C., Acad. Rep. Populare Române, Filiala Cluj, St. Cerc. Chim., 1959, vol. 10, p. 145.

    Google Scholar 

  5. Achkasova, A.A. and El’chaninov, M.M., Chem. Heterocycl. Compd., 1983, vol. 42, no. 2, p. 166. doi https://doi.org/10.1007/s10593-006-0065-7

    Article  Google Scholar 

  6. Melnikova, E.B., El’chaninov, M.M, Milov, A.A., and Lukyanov, B.S., Chem. Heterocycl. Compd., 2008, vol. 44, no. 9, p. 1070. doi https://doi.org/10.1007/s10593-008-0156-8

    Article  CAS  Google Scholar 

  7. El’chaninov, M.M, Simonov, A.M., and Oleinikova, L.Ya., Chem. Heterocycl. Compd., 1983, vol. 19, no. 10, p. 1041. doi https://doi.org/10.1007/BF00505746

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M.I. Platov South Russian State Polytechnic University (NPI), pr. Prosveshcheniya 132, Novocherkassk, 346428, Russia

    A. A. Aleksandrov, M. M. El’chaninov & D. A. Zablotskii

Authors
  1. A. A. Aleksandrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. M. El’chaninov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. A. Zablotskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Aleksandrov.

Additional information

Russian Text © A.A. Aleksandrov, M.M. El’chaninov, D.A. Zablotskii, 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 1, pp. 45–50.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aleksandrov, A.A., El’chaninov, M.M. & Zablotskii, D.A. 2-(Fur-2-yl)thiazolo[4,5-f]quinoline: Synthesis and Electrophilic Substitution Reactions. Russ J Gen Chem 89, 37–41 (2019). https://doi.org/10.1134/S1070363219010079

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219010079

Keywords

Search

Navigation