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3,5-[5-Arylisoxazol-3-yl(4,5-dichloroisothiazol-3-yl)]-substituted 1,2,4- and 1,3,4-oxadiazoles: synthesis, palladium complexes, and catalysis of Suzuki reactions in aqueous media

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Chemistry of Heterocyclic Compounds Aims and scope

A reaction sequence involving transformations of 5-(4-methylphenyl)isoxazole and 4,5-dichloroisothiazole derivatives containing an amidoxime group at position 3 allowed to synthesize the respective 3,5-isoxazolyl(isothiazolyl)-substituted 1,2,4-oxadiazoles. Selective recyclization of 4,5-dichloro-3-(1Н-tetrazol-5-yl)isothiazole and 5-(4-methylphenyl)-3-(1Н-tetrazol-5-yl)isoxazole gave 2,5-isoxazolyl-(isothiazolyl)-substituted 1,3,4-oxadiazoles. The obtained compounds combining three azole heterocycles in one molecule formed palladium complexes that showed high catalytic activity in Suzuki reactions in aqueous and aqueous alcohol media. The bimetallic reusable Pd/Fe catalyst obtained from palladium polyazole complex retained high catalytic activity after five uses.

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This work received financial support from the Russian Foundation for Basic Research (grants 16-58-00059-Bel_a, 17-08-00633) and the Belarusian Republican Foundation for Fundamental Research (grant Х16Р-006).

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Authors and Affiliations

  1. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Nikolay A. Bumagin

  2. Institute of Physical Organic Chemistry, National Academy of Science of Belarus, 31 Surganova St., 220072, Minsk, Belarus

    Sergey K. Petkevich, Alexey V. Kletskov & Vladimir I. Potkin

Authors
  1. Nikolay A. Bumagin
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  2. Sergey K. Petkevich
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  3. Alexey V. Kletskov
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  4. Vladimir I. Potkin
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Correspondence to Nikolay A. Bumagin or Vladimir I. Potkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(12), 1340–1349

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Bumagin, N.A., Petkevich, S.K., Kletskov, A.V. et al. 3,5-[5-Arylisoxazol-3-yl(4,5-dichloroisothiazol-3-yl)]-substituted 1,2,4- and 1,3,4-oxadiazoles: synthesis, palladium complexes, and catalysis of Suzuki reactions in aqueous media. Chem Heterocycl Comp 53, 1340–1349 (2017). https://doi.org/10.1007/s10593-018-2216-z

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