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Russian Journal of General Chemistry

, Volume 88, Issue 2, pp 234–240 | Cite as

Synthesis of Fluorine-Containing Derivatives of 5-Arylisoxazoles and 4,5-Dichlorothiazole

  • S. K. Petkevich
  • E. A. Dikusar
  • A. V. Kletskov
  • I. B. Rozenzveig
  • G. G. Levkovskaya
  • P. V. Kurman
  • R. M. Zolotar’
  • V. I. Potkin
Article
  • 31 Downloads

Abstract

Alkylation of fluorophenols and phenolic aldehydes with 5-phenyl(p-tolyl)-3-chloromethylisoxazole under the Williamson reaction conditions afforded the corresponding ethers. Condensation of the resulting phenolic aldehyde derivatives and 5-phenyl(p-tolyl)isoxazole-3-carbaldehydes with p-fluoroaniline resulted in fluorine-containing azomethines. Acylation of fluorinated amines with 5-(p-tolyl)isoxazole- and 4,5- dichloroisothiazole-3-carbonyl chlorides gave rise to fluorinated amides bearing isoxazole and isothiazole fragments, representatives of which showed a synergistic effect in compositions with insecticides.

Keywords

5-arylisoxazoles isothiazoles ethers azomethines amides 

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References

  1. 1.
    Gouverneur, V. and Seppelt, K., Chem. Rev., 2015, vol. 115, no. 2, p. 563. doi 10.1021/cr500686kCrossRefGoogle Scholar
  2. 2.
    Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E., Smart, B.E., and Tatlow, J.C., Eds., New York; London: Plenum Press, 1994.Google Scholar
  3. 3.
    Zhou, Yu., Wang, J., Gu, Zh., Wang, S., Zhu, W., Acena, J.L., Soloshonok, V.A., Izawa, K., and Liu, H., Chem. Rev., 2016, vol. 116, no. 2, p. 422. doi 10.1021/acs.chemrev.5b00392CrossRefGoogle Scholar
  4. 4.
    Isanbor, Ch. and O’Hagan, D., J. Fluor. Chem., 2006, vol. 127, no. 3, p. 303. doi 10.1016/j.jfluchem.2006.01.011CrossRefGoogle Scholar
  5. 5.
    Mori, T. and Matsuo, N., J. Synth. Org. Chem. Japan, 2007, vol. 65, no. 6, p. 620.CrossRefGoogle Scholar
  6. 6.
    Kulchitsky, V.A., Potkin, V.I., Zubenko, Yu.S., Chernov, A.N., Talabaev, M.V., Demidchik, Yu.E., Petkevich, S.K., Kazbanov, V.V., Gurinovich, T.A., Roeva, M.O., Grigoriev, D.G., Kletskov, A.V., and Kalunov, V.N., Med. Chem., 2012, vol. 8, no. 1, p. 22. doi 10.2174/157340612799278298CrossRefGoogle Scholar
  7. 7.
    Potkin, V.I., Kletskov, A.V., Petkevich, S.K., Pashkevich, S.G., Kazbanov, V.V., Denisov, A.A., and Kulchitsky, V.A., Heterocycl. Lett., 2015, vol. 1, no. 1, p. 11.Google Scholar
  8. 8.
    Wainberg, Z.A., Anghel, A., Rogers, A.M., Desai, A.J., Kalous, O., Conklin, D., Ayala, R., O'Brien, N.A., Quadt, C., Akimov, M., Slamon, D.J., and Finn, R.S., Mol. Cancer Ther., 2013, vol. 12, no. 4, p. 509. doi 10.1158/1535-7163.MCT-12-0507CrossRefGoogle Scholar
  9. 9.
    Nikitin, A.Ya., Potkin, V.I., Bazanova, L.P., Levkovskaya, G.G., Petkevich, S.K., and Kletskov, A.V., Dezinfektsionnoe Delo, 2014, no. 2, p. 23.Google Scholar
  10. 10.
    Kletskov, A.V., Potkin, V.I., Dikusar, E.A., and Zolotar’, R.M., Nat. Prod. Commun., 2017, vol. 12, no. 1, p. 105.Google Scholar
  11. 11.
    Potkin, V.I., Petkevich, S.K., Kletskov, A.V., Dikusar, E.A., Zubenko, Yu.S., Zhukovskaya, N.A., Kazbanov, V.V., and Pashkevich, S.G., Russ. J. Org. Chem., 2013, vol. 49, no. 10, p. 1523. doi 10.1134/S1070428013100205CrossRefGoogle Scholar
  12. 12.
    Potkin, V.I., Bumagin, N.A., Petkevich, S.K., Dikusar, E.A., Semenova, E.A., Kurman, P.V., Zolotar’, R.M., Pashkevich, S.G., Gurinovich, T.A., and Kulchitsky, V.A., Russ. J. Org. Chem., 2015, vol. 51, no. 8, p. 1119. doi 10.1134/S1070428015080102CrossRefGoogle Scholar
  13. 13.
    Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Personal Reactions in Organic Chemistry), Moscow: Khimiya, 1976.Google Scholar
  14. 14.
    Saleem, L.M.N., Org. Magn. Reson., 1982, vol. 19, no. 4, p. 176. doi 10.1002/mrc.1270190403CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • S. K. Petkevich
    • 1
  • E. A. Dikusar
    • 1
  • A. V. Kletskov
    • 1
  • I. B. Rozenzveig
    • 2
  • G. G. Levkovskaya
    • 2
  • P. V. Kurman
    • 3
  • R. M. Zolotar’
    • 3
  • V. I. Potkin
    • 1
  1. 1.Institute of Physical Organic ChemistryNational Academy of Sciences of BelarusMinskBelarus
  2. 2.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia
  3. 3.Institute of Bioorganic ChemistryNational Academy of Sciences of BelarusMinskBelarus

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