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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 3, pp 369–374 | Cite as

Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines

  • Aynur R. MakhmutovEmail author
  • Akhat G. Mustafin
  • Salavat M. Usmanov
Article

A one-pot tandem synthesis of substituted quinolines involving selective catalytic oxidation of primary alcohols to the corresponding aldehydes and their subsequent condensation with arylamines has been developed. Fe(CrO2)2 has been used as a catalyst, and oxidation has been performed with aqueous H2O2. To accelerate the catalytic oxidation of alcohols, photoactivation method has been applied.

Keywords

arylamines primary alcohols substituted quinolines iron-containing catalyst photoactivation 

Notes

Authors thank Center for the Collective Use “Chemistry” of the Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences.

References

  1. 1.
    Yamamoto, N.; Obora, Y.; Ishii, Y. J. Org. Chem. 2011, 76, 2937.CrossRefPubMedGoogle Scholar
  2. 2.
    Schley, N. D.; Dobereiner, G. E.; Crabtree, R. H. Organometallics 2011, 30, 4174.CrossRefGoogle Scholar
  3. 3.
    Lee, E. Y.; Kim, Y.; Lee, J. S.; Park, J. Eur. J. Org. Chem. 2009, 2943.Google Scholar
  4. 4.
    Obora, Y.; Ishii, Y. Synlett 2011, 30.Google Scholar
  5. 5.
    Simon, M.-O.; Ung, G.; Darses, S. Adv. Synth. Catal. 2011, 353, 1045.CrossRefGoogle Scholar
  6. 6.
    Gunanathan, C.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2009, 131, 3146.CrossRefPubMedGoogle Scholar
  7. 7.
    (a) Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. Org. Biomol. Chem. 2012, 10, 240. (b) Watson, A. J. A.; Maxwell, A. C.; Williams, J. M. J. Org. Lett. 2009, 11, 2667.Google Scholar
  8. 8.
    Tursky, M.; Lorentz-Petersen, L. L. R.; Olsen, L. B.; Madsen, R. Org. Biomol. Chem. 2010, 8, 5576.CrossRefPubMedGoogle Scholar
  9. 9.
    (a) Khusnutdinov, R. I.; Bayguzina, A. R.; Aminov, R. I. Russ. Chem. Bull., Int. Ed. 2013, 62, 133. [Izv. Akad. Nauk, Ser. Khim. 2013, 134.] (b) Khusnutdinov, R. I.; Bayguzina, A. R.; Aminov, R. I. Russ. J. Gen. Chem. 2015, 85, 2725. [Zh. Obshch. Khim. 2015, 1993.] (c) Khusnutdinov, R. I.; Bayguzina, A. R.; Aminov, R. I. Russ. J. Gen. Chem. 2016, 86, 1613. [Zh. Obshch. Khim. 2016, 1135.]Google Scholar
  10. 10.
    Eggins, B. R. Chemical Sensors and Biosensors; Wiley: Chichester, 2002, p. 142.Google Scholar
  11. 11.
    Makhmutov, A. R.; Usmanov, S. M. Bashkir. Khim. Zh. 2017, 24(1), 18.Google Scholar
  12. 12.
    Makhmutov, A. R.; Usmanov, S. M. Bashkir. Khim. Zh. 2017, 24(4), 33.Google Scholar
  13. 13.
    (a) Walling, C. Acc. Chem. Res. 1975, 8, 125. (b) Tyre, B. W.; Watts, R. J.; Miller, G. C. J. Environ. Qual. 1991, 20, 832.Google Scholar
  14. 14.
    Barbusiński, K. Ecol. Chem. Eng. S 2009, 16, 347.Google Scholar
  15. 15.
    Bulgakov, R. G.; Kuleshov, S. P.; Vafin, R. R.; Dzhemilev, U. M. Russ. J. Org. Chem. 2009, 45, 944. [Zh. Org. Khim. 2009, 956.]Google Scholar
  16. 16.
    Makhmutov, A. R.; Usmanov, S. M. Bashkir. Khim. Zh. 2017, 24(3), 45.Google Scholar
  17. 17.
    Makhmutov, A. R. J. Sib. Fed. Univ., Chem. 2017, 10, 154.Google Scholar
  18. 18.
    (a) Pozdnyakov, I. P.; Vorobyev, D. Yu.; Glebov, E. M.; Plyusnin, V. F.; Grivin, V. P.; Ivanov, Y. V.; Bazhin, N. M. Mendeleev Commun. 2000, 10, 185. (b) Pozdnyakov, I. P.; Plyusnin, V. F.; Glebov, E. M.; Grivin, V. P.; Vorobyev, D. Yu.; Bazhin, N. M.; Sosedova, Yu. A. Int. J. Photoenergy 2004, 6, 89.Google Scholar
  19. 19.
    (a) Bulgakov, R. G.; Kuleshov, S. P.; Makhmutov, A. R.; Dzhemilev, U. M. Kinet. Catal. 2010, 51, 534. (b) Bulgakov, R. G.; Kuleshov, S. P.; Makhmutov, A. R. Russ. Chem. Bull., Int. Ed. 2007, 56, 443. [Izv. Akad. Nauk, Ser. Khim. 2007, 429.]Google Scholar
  20. 20.
    Bulgakov, R. G.; Kuleshov, S. P.; Makhmutov, A. R.; Dzhemilev, U. M. Russ. J. Org. Chem. 2006, 42, 1573. [Zh. Org. Khim. 2006, 1583.]Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Aynur R. Makhmutov
    • 1
    Email author
  • Akhat G. Mustafin
    • 1
  • Salavat M. Usmanov
    • 1
  1. 1.Bashkir State UniversityUfaRussia

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