SYNTHESIS OF ISOXAZOLYLVINYL KETONES FROM SUBSTITUTED FURANS

Authors

  • Olga V. Serdyuk Department of Chemistry and Pharmacy, Institute of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nürnberg, 10 Nikolaus-Fiebiger-St., Erlangen 91058, Germany
  • Frank Hampel Department of Chemistry and Pharmacy, Institute of Organic Chemistry I, Friedrich-Alexander University of Erlangen-Nürnberg, 10 Nikolaus-Fiebiger-St., Erlangen 91058, Germany
  • Vladimir T. Abaev North Ossetian State University named after K. L. Khetagurov, 43–46 Vatutina St., Vladikavkaz 362025, Russia Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355009, Russia

DOI:

https://doi.org/10.1007/6003

Keywords:

chalcone, furan, isoxazole, ring opening – ring closure reaction.

Abstract

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.

Author Biographies

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

Department of Chemistry and Pharmacy

Institute of Organic Chemistry I

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

Department of Chemistry and Pharmacy

Institute of Organic Chemistry I

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Published

2020-11-26

Issue

Vol. 56 No. 11 (2020)

Section

Original Papers