Skip to main content
Log in

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

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

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Gouverneur, V. and Seppelt, K., Chem. Rev., 2015, vol. 115, no. 2, p. 563. doi 10.1021/cr500686k

    Article  CAS  Google Scholar 

  2. Organofluorine Chemistry: Principles and Commercial Applications, Banks, R.E., Smart, B.E., and Tatlow, J.C., Eds., New York; London: Plenum Press, 1994.

  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.5b00392

    Article  CAS  Google Scholar 

  4. Isanbor, Ch. and O’Hagan, D., J. Fluor. Chem., 2006, vol. 127, no. 3, p. 303. doi 10.1016/j.jfluchem.2006.01.011

    Article  CAS  Google Scholar 

  5. Mori, T. and Matsuo, N., J. Synth. Org. Chem. Japan, 2007, vol. 65, no. 6, p. 620.

    Article  CAS  Google Scholar 

  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 10.2174/157340612799278298

    Article  CAS  Google Scholar 

  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. 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-12-0507

    Article  CAS  Google Scholar 

  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. 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. 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/S1070428013100205

    Article  CAS  Google Scholar 

  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/S1070428015080102

    Article  CAS  Google Scholar 

  13. Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Personal Reactions in Organic Chemistry), Moscow: Khimiya, 1976.

    Google Scholar 

  14. Saleem, L.M.N., Org. Magn. Reson., 1982, vol. 19, no. 4, p. 176. doi 10.1002/mrc.1270190403

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. K. Petkevich.

Additional information

Original Russian Text © S.K. Petkevich, E.A. Dikusar, A.V. Kletskov, I.B. Rozenzveig, G.G. Levkovskaya, P.V. Kurman, R.M. Zolotar’, V.I. Potkin, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 2, pp. 255–261.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Petkevich, S.K., Dikusar, E.A., Kletskov, A.V. et al. Synthesis of Fluorine-Containing Derivatives of 5-Arylisoxazoles and 4,5-Dichlorothiazole. Russ J Gen Chem 88, 234–240 (2018). https://doi.org/10.1134/S1070363218020081

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218020081

Keywords

Navigation