Russian Journal of Organic Chemistry

, Volume 54, Issue 8, pp 1166–1172 | Cite as

One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium

  • A. R. MakhmutovEmail author


One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.


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  1. 1.
    Yamamoto, N., Obora, Y., and Ishii, Y., J. Org. Chem., 2011, vol. 76, p. 2937.CrossRefPubMedGoogle Scholar
  2. 2.
    Schley, N.D., Dobereiner, G.E., and Crabtree, R.H., Organometallics, 2011, vol. 30, p. 4174.CrossRefGoogle Scholar
  3. 3.
    Lee, E.Y., Kim, Y., Lee, J.S., and Park, J., Eur. J. Org. Chem., 2009, vol. 18, p. 2943.CrossRefGoogle Scholar
  4. 4.
    Obora, Y. and Ishii, Y., Synlett., 2011, p.30.Google Scholar
  5. 5.
    Simon, M.O., Ung, G., and Darses, S., Adv. Synth. Catal., 2011, vol. 353, p. 1045.CrossRefGoogle Scholar
  6. 6.
    Gunanathan, C., Shimon, L.J.W., and Milstein, D., J. Am. Chem. Soc., 2009, vol. 131, p. 3146.CrossRefPubMedGoogle Scholar
  7. 7.
    Watson, A.J.A., Maxwell, A.C., and Williams, J.M.J., Org. Biomol. Chem., 2012, vol. 10, p.240.CrossRefPubMedGoogle Scholar
  8. 8.
    Watson, A.J.A., Maxwell, A.C., and Williams, J.M.J., Org. Lett., 2009, vol. 11, p. 2667.CrossRefPubMedGoogle Scholar
  9. 9.
    Tursky, M., Lorentz-Petersen, L.L.R., Olsen, L.B., and Madsen, R., Org. Biomol. Chem., 2010, vol. 8, p. 5576.CrossRefPubMedGoogle Scholar
  10. 10.
    Khusnutdinov, R.I., Bayguzina, A.R., and Aminov, R.I., Russ. Chem. Bull., 2013, vol. 62, p. 133. doi 10.1007/s11172-013-0019-zCrossRefGoogle Scholar
  11. 11.
    Eggins, B.R., Chemical Sensors and Biosensors, UK: Wiley, 2002.Google Scholar
  12. 12.
    Makhmutov, A.R. and Usmanov, S.M., Bashkir. Khim. Zh., 2017, vol. 24, p.18.Google Scholar
  13. 13.
    Makhmutov, A.R. and Usmanov, S.M., Bashkir. Khim. Zh., 2017, vol. 24, p.33.Google Scholar
  14. 14.
    Walling, A., Acc. Chem. Res., 1975, vol. 8, p.125.CrossRefGoogle Scholar
  15. 15.
    Tyre, B.W., Watts, R.J., and Miller, G.C., Envir. Quality, 1991, vol. 20, p.832.CrossRefGoogle Scholar
  16. 16.
    Barbusiñski, K., Ecolog. Chem. Eng., 2009, vol. 16, p.347.Google Scholar
  17. 17.
    Bulgakov, R.G., Kuleshov, S.P., Vafin, R.R., and Dzhemilev, U.M., Russ. J. Org. Chem., 2009, vol. 45, p. 944. doi 10.1134/S1070428009060268CrossRefGoogle Scholar
  18. 18.
    Makhmutov, A.R. and Usmanov, S.M., Bashkir. Khim. Zh., 2017, vol. 24, p.45.Google Scholar
  19. 19.
    Makhmutov, A.R., Zh. Sib. Fed. Univer., 2017, vol. 10, p.154.CrossRefGoogle Scholar
  20. 20.
    Pozdnyakov, I.P., Vorobyev, D.Yu., Glebov, E.M., Plyusnin, V.F., Grivin, V.P., Ivanov, Y.V., and Bazhin, N.M., Mendeleev Commun., 2000, vol. 10, p.185.CrossRefGoogle Scholar
  21. 21.
    Pozdnyakov, I.P., Plyusnin, V.F., Glebov, E.M., Grivin, V.F., Vorobyev, D.Yu., Bazhin, N.M., and Sosedova, Yu.A., Int. J. Photoenergy, 2004, vol. 6, p.89.CrossRefGoogle Scholar
  22. 22.
    Bulgakov, R.G., Kuleshov, S.P., Makhmutov, A.R., and Dzhemilev, U.M., Kinet. Catal., 2010, vol. 51, p. 534. doi 10.1134/S0023158410040129CrossRefGoogle Scholar
  23. 23.
    Bulgakov, R.G., Kuleshov, S.P., and Makhmutov, A.R., Russ. Chem. Bull., 2007, vol. 56, p. 443. doi 10.1007/s11172-007-0071-7CrossRefGoogle Scholar
  24. 24.
    Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Jr., Organic Solvents: Physical Properties and Methods of Purification, New York: Wiley, 1955.Google Scholar
  25. 25.
    Makhmutov, A.R., Mustafin, A.G., and Usmanov, S.M., Chem. Heterocycl. Compd., 2018, vol. 54, p. 369. doi 10.1007/s10593-018-2275-1CrossRefGoogle Scholar

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© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.Bashkir State UniversityUfa, BashkortostanRussia

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