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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1340–1349 | Cite as

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

  • Nikolay A. BumaginEmail author
  • Sergey K. Petkevich
  • Alexey V. Kletskov
  • Vladimir I. PotkinEmail author
Article

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.

Keywords

isoxazoles isothiazoles 1,2,4-oxadiazoles 1,3,4-oxadiazoles palladium complexes heterocyclization heterogeneous catalysis homogeneous catalysis magnetic Pd/Fe catalyst Suzuki reaction 

Notes

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. 1.Lomonosov Moscow State UniversityMoscowRussia
  2. 2.Institute of Physical Organic Chemistry, National Academy of Science of BelarusMinskBelarus

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