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...


phenacylfurans furans cyclopentenones recyclization 


  1. 1.
    C. Fionda, F. Nappi, M. Piccoli, L. Frati, A. Santoni, and M. Cippitelli, Mol. Pharmacol., 72, 1246 (2007).CrossRefGoogle Scholar
  2. 2.
    E. Cernuda-Morollón, E. Pineda-Molina, F. J. Cañada, and D. Pérez-Sala, J. Biol. Chem., 276, 35530 (2001).CrossRefGoogle Scholar
  3. 3.
    K. Tonari, K. Machiya, I. Ichimoto, and H. Ueda, Agric. Biol. Chem., 45, 295 (1981).CrossRefGoogle Scholar
  4. 4.
    R. D'Ascoli, M. D'Auria, C. Iavarone, G. Piancatelli, and A. Scettri, J. Org. Chem., 45, 4502 (1980).CrossRefGoogle Scholar
  5. 5.
    Y. Liu, R.-J. Song, and J.-H. Li, Synthesis, 3663 (2010).Google Scholar
  6. 6.
    E. Holtz, V. Köhler, B. Appel, and P. Langer, Eur. J. Org. Chem., 532 (2005).Google Scholar
  7. 7.
    G. Piancatelli, M. D'Auria, and F. D'Onofrio, Synthesis, 867 (1994).Google Scholar
  8. 8.
    F. D'Onofrio, G. Piancatelli, and M. Nicolai, Tetrahedron, 51, 4083 (1995).CrossRefGoogle Scholar
  9. 9.
    G. Csákÿ, M. Mba, and J. Plumet, Tetrahedron Asymm., 15, 647 (2004).CrossRefGoogle Scholar
  10. 10.
    V. T. Abaev, K. V. Bosikova, O. V. Serdyuk, and A. V. Butin, Khim. Geterotsikl. Soedin., 772 (2009). [Chem. Heterocycl. Comp., 45, 611 (2009)].Google Scholar

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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