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Synthesis of 5-Arylisoxazole and 4,5-Dichloroisothiazole Amino-Substituted Derivatives and Their Biological Activity

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Abstract

A series of amino derivatives of 5-arylisoxazoles and 4,5-dichloroisothiazole with primary and secondary amino groups was synthesized. 3-Aminomethyl-5-arylisoxazol-3-ylmethanamines were obtained on the basis of 5-aryl-3-(chloromethyl)isoxazoles using the Gabriel phthalimide method. 5-Arylisoxazol-3-yl- and 4,5-dichloroisothiazol-3-ylallylamines were synthesized in two ways: reduction of azomethines obtained by condensation of 5-arylisoxazolyl- and 4,5-dichloroisothiazolyl-3-carbaldehydes with allylamine, and by nucleophilic substitution of the chlorine atom in 3-chloromethyl derivatives of the corresponding azoles by reaction with allylamine. Amides and sulfonamides of azolylallylamines were synthesized. Some of the compounds obtained showed antibacterial and fungicidal activity.

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Funding

This work was supported by the Belarusian Republican Foundation for Basic Research (project no. X19PM-003) and the Russian Foundation for Basic Research (project no. 19-53-04002).

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry of the National Academy of Sciences of Belarus, 220072, Minsk, Belarus

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

  2. Peoples’ Friendship University of Russia, 117198, Moscow, Russia

    D. F. Mertsalov, L. V. Chervyakova & M. A. Nadirova

  3. Gause Institute of New Antibiotics, 119021, Moscow, Russia

    A. P. Tyurin

  4. State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd, 110021, Shenyang, China

    A. Y. Guan & C. L. Liu

Authors
  1. I. A. Kolesnik
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  2. S. K. Petkevich
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  3. D. F. Mertsalov
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  4. L. V. Chervyakova
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  5. M. A. Nadirova
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  6. A. P. Tyurin
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  7. A. Y. Guan
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  8. C. L. Liu
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  9. V. I. Potkin
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Correspondence to I. A. Kolesnik.

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Kolesnik, I.A., Petkevich, S.K., Mertsalov, D.F. et al. Synthesis of 5-Arylisoxazole and 4,5-Dichloroisothiazole Amino-Substituted Derivatives and Their Biological Activity. Russ J Gen Chem 92, 29–39 (2022). https://doi.org/10.1134/S1070363222010066

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