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Synthesis of functional isoxazole derivatives proceeding from (5-arylisoxazol-3-yl)chloromethanes

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Abstract

Reaction of 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles with substituted phenols under the conditions of Williamson reaction afforded the corresponding 3-aryloxymethyl-5-phenyl(p-tolyl)isoxazoles. Treating the latter with sodium methylate, sodium phenyl(benzyl, furfuryl)thiolates and morpholine in methanol resulted in the replacement of the chlorine atom in 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles by methoxy-, phenyl-(benzyl, furfuryl)sulfanyl groups and morpholine residue.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    V. I. Potkin, S. K. Petkevich, E. A. Dikusar & E. V. Semenova

  2. Lomonosov Moscow State University, Moscow, Russia

    N. A. Bumagin

  3. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus

    P. V. Kurman & R. M. Zolotar’

  4. Physiology Institute, National Academy of Sciences of Belarus, Minsk, Belarus

    S. G. Pashkevich, T. A. Gurinovich & V. A. Kul’chitskii

Authors
  1. V. I. Potkin
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  2. N. A. Bumagin
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  3. S. K. Petkevich
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  4. E. A. Dikusar
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  5. E. V. Semenova
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  6. P. V. Kurman
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  7. R. M. Zolotar’
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  8. S. G. Pashkevich
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  9. T. A. Gurinovich
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  10. V. A. Kul’chitskii
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Corresponding author

Correspondence to V. I. Potkin.

Additional information

Original Russian Text © V.I. Potkin, N.A. Bumagin, S.K. Petkevich, E.A. Dikusar, E.V. Semenova, P.V. Kurman, R.M. Zolotar’, S.G. Pashkevich, T.A. Gurinovich, V.A. Kul’chitskii, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 8, pp. 1140–1150.

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Potkin, V.I., Bumagin, N.A., Petkevich, S.K. et al. Synthesis of functional isoxazole derivatives proceeding from (5-arylisoxazol-3-yl)chloromethanes. Russ J Org Chem 51, 1119–1130 (2015). https://doi.org/10.1134/S1070428015080102

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  • DOI: https://doi.org/10.1134/S1070428015080102

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