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Synthesis of Isoxazolylvinyl Ketones from Substituted Furans

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Chemistry of Heterocyclic Compounds Aims and scope

A new method for the preparation of isoxazolylvinyl ketones related to potential cytotoxic agents has been developed. In the first step, the reaction of furfuryl ketones with hydroxylamine hydrochloride affords the corresponding oximes. Further, the oxidative ring opening – ring closure reaction of oximes leads to isoxazoles with an α, β-unsaturated carbonyl motif. The developed procedure is metal-free and does not require expensive starting materials.

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Authors and Affiliations

  1. Department of Chemistry and Pharmacy, Institute of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nürnberg, 10 Nikolaus-Fiebiger-St, 91058, Erlangen, Germany

    Olga V. Serdyuk & Frank Hampel

  2. North Ossetian State University named after K. L. Khetagurov, 43–46 Vatutina St, Vladikavkaz, 362025, Russia

    Vladimir T. Abaev

  3. Department of Chemistry, North Caucasus Federal University, 1a Pushkina St, Stavropol, 355009, Russia

    Vladimir T. Abaev

Authors
  1. Olga V. Serdyuk
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  2. Frank Hampel
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  3. Vladimir T. Abaev
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Correspondence to Olga V. Serdyuk.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(11), 1477–1484

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Serdyuk, O.V., Hampel, F. & Abaev, V.T. Synthesis of Isoxazolylvinyl Ketones from Substituted Furans. Chem Heterocycl Comp 56, 1477–1484 (2020). https://doi.org/10.1007/s10593-020-02841-y

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  • DOI: https://doi.org/10.1007/s10593-020-02841-y

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