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Synthesis of functional derivatives of isothiazole and isoxazole basing on (5-arylizoxazol-3-yl)- and (4,5-dichloroisothiazol-3-yl)arylmethanol

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Abstract

From (4,5-dichloroisothiazol-3-yl)phenylmethanol by Ritter reaction a substituted acetamide was synthesized that at hydrolysis with HCl afforded (4,5-dichloroisothiazol-3-yl)phenylmethylamine hydrochloride. By reaction of (5-arylisoxazol-3-yl)- and 4,5-dichloroisothiazol-3-yl)arylmethanol with thionyl chloride the corresponding (1,2-azol-3-yl)arylchloromethanes were obtained. At treatment with O- and N-nucleophiles chlorine atom in chloromethylеne fragment of obtained compounds was substituted by residues of benzylamine, morpholine, vanillin, and ethoxy group.

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Authors and Affiliations

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

    V. I. Potkin, A. V. Kletskov & S. K. Petkevich

  2. Lomonosov Moscow State University, Moscow, 119991, Russia

    N. A. Bumagin

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

    P. V. Kurman

Authors
  1. V. I. Potkin
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  2. N. A. Bumagin
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  3. A. V. Kletskov
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  4. S. K. Petkevich
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  5. P. V. Kurman
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Correspondence to V. I. Potkin.

Additional information

Original Russian Text © V.I. Potkin, N.А. Bumagin, А.V. Kletskov, S.K. Petkevich, P.V. Kurman, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 11, pp. 1666–1674.

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Potkin, V.I., Bumagin, N.A., Kletskov, A.V. et al. Synthesis of functional derivatives of isothiazole and isoxazole basing on (5-arylizoxazol-3-yl)- and (4,5-dichloroisothiazol-3-yl)arylmethanol. Russ J Org Chem 52, 1661–1669 (2016). https://doi.org/10.1134/S1070428016110191

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  • DOI: https://doi.org/10.1134/S1070428016110191

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