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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 7, pp 906–908 | Cite as

Synthesis of new cyclopentenones from phenacylfurans

  • O. V. SerdyukEmail author
  • V. T. Abaev
  • A. V. ButinEmail author
Letters to the Editor

Substituted cyclopentenones are known as precursors of modified prostaglandins [1,2] and compounds displaying various kinds of biological activity [3]. Despite the many methods for the preparation of cyclopente-nones, there have been only a few methods described for the synthesis of such systems containing an acyl group [4, 5, 6]. 1,4-Dicarbonyl compounds (in one-step procedures) or furan derivatives (in two-step procedures) have often been used as starting compounds [7]. There have been only very few examples of the preparation of cyclopentenones from furans in one step [6,8,9]. We propose the use of phenacylfurans 1 recently obtained in our laboratory [10] for this purpose.

Indeed, we have found that the treatment of phenacylfurans 1a,b with a mixture of acetic and hydrochlo-ric acids leads to cyclopentenones 2 and 3. The reaction proceeds at room temperature in good yield. 1H NMR spectra of the crude product mixtures indicated the formation of isomeric cyclopentenones 2 and 3in...

Keywords

phenacylfurans furans cyclopentenones recyclization 

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  1. 1.Southern Federal University, Department of ChemistryRostov-on-DonRussia
  2. 2.North Ossetian State UniversityVladikavkazRussia
  3. 3.Research Institute of Heterocyclic Compounds ChemistryKuban State Technological UniversityKrasnodarRussia

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