Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1496–1500 | Cite as

Bimolecular Condensation of 1-(para-tolyl)-and 1-(biphenyl-4-yl)-3,4,4-trichloro-3-buten-1-ones to 2,3,4,6-substituted 4Н-pyrans*

  • V. I. PotkinEmail author
  • S. K. Petkevich
  • P. V. Kurman
  • G. G. Levkovskaya
  • L. S. Ivashkevich
  • A. S. Lyakhov

Compounds of pyran series have been known for a long time, yet they still attract a steady interest due to the high biological activity caused by the affinity of pyran fragment towards various receptors [1, 2, 3]. The biological action of pyrans largely depend on the functional groups bonded to the heterocycle, which also define the possibilities of using these compounds for directed synthesis of useful products [4, 5, 6]. Functionally substituted pyrans are structural fragments of many natural biologically active compounds [7], pesticides [8], antibacterials [9, 10, 11], and antitumor drugs [12, 13]. Besides that, 4-methylene-4Н-pyrans are considered as promising materials for organic LED devices [14].

Various methods for the construction of pyran heterocycle are known, including those based on the use of unsaturated ketones. Thus, alkyl β,β-dichlorovinyl ketones, containing an activated methylene group, undergo crotonic condensation in the presence of anhydrous AlCl3 or Mg(ClO4)2...


aryl trichloroallyl ketones guanidine pyrans condensation heterocyclization isomerization tautomerism 


This work received financial support from the Belarusian Republican Foundation for Fundamental Research (grant Kh12СО-012) and the Siberian Branch of Russian Academy of Sciences (grant No. 21).

Supplementary material

10593_2014_1614_MOESM1_ESM.pdf (377 kb)
ESM 1 (PDF 376 kb)


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. I. Potkin
    • 1
    Email author
  • S. K. Petkevich
    • 1
  • P. V. Kurman
    • 2
  • G. G. Levkovskaya
    • 3
  • L. S. Ivashkevich
    • 4
  • A. S. Lyakhov
    • 4
  1. 1.Institute of Physical Organic ChemistryNational Academy of Sciences of BelarusMinskBelarus
  2. 2.Institute of Bioorganic ChemistryNational Academy of Sciences of BelarusMinskBelarus
  3. 3.A. E. Favorsky Irkutsk Institute of ChemistrySiberian Branch of the Russian Academy of SciencesIrkutskRussia
  4. 4.Research Institute of Physical Chemical ProblemsBelarusian State UniversityMinskBelarus

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