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Russian Journal of General Chemistry

, Volume 89, Issue 1, pp 37–41 | Cite as

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

  • A. A. AleksandrovEmail author
  • M. M. El’chaninov
  • D. A. Zablotskii
Article
  • 6 Downloads

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.

Keywords

quinoline-5-amine furan-2-carbonyl chloride potassium ferricyanide 2-(fur-2-yl)thiazolo[4,5-f]-quinoline electrophilic substitution reactions 

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References

  1. 1.
    Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Heterocycles in Life and Society, Chichester: J. Wiley & Sons, 1997.Google Scholar
  2. 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. 3.
    Jacobson, P., Ber., 1886, vol. 19, pp. 1067, 1811.CrossRefGoogle Scholar
  4. 4.
    Fărcăşan, V. and Makkay, C., Acad. Rep. Populare Române, Filiala Cluj, St. Cerc. Chim., 1959, vol. 10, p. 145.Google Scholar
  5. 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 CrossRefGoogle Scholar
  6. 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 CrossRefGoogle Scholar
  7. 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 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. A. Aleksandrov
    • 1
    Email author
  • M. M. El’chaninov
    • 1
  • D. A. Zablotskii
    • 1
  1. 1.M.I. Platov South Russian State Polytechnic University (NPI)NovocherkasskRussia

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