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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 887–892 | Cite as

Synthesis of 5-polyfluoroalkyl-4-(p-tolyl-sulfonyl)pyrazoles and 4-polyfluoroalkyl-5-(p-tolylsulfonyl)pyrimidines from 1-dimethylamino-2-(p-tolylsulfonyl)-polyfluoro-1-alken-3-ones

  • O. S. Kanishchev
  • Yu. P. Bandera
  • V. M. Timoshenko
  • E. B. Rusanov
  • S. A. But
  • Yu. G. Shermolovich
Article

Abstract

1-Dimethylamino-2-(p-tolylsulfonyl)polyfluoro-1-alken-3-ones were obtained from hydrates of 3,3,3-trifluoro-1-(p-tolylsulfonyl)-2-propanone and 3,3,4,4,5,5-hexafluoro-1-(p-tolylsulfonyl)-2-pentanone under conditions of the Vilsmeier-Haack-Arnold reaction. The analogous reaction of 3,3-difluoro-1-(p-tolylsulfonyl)-2-propanone hydrate leads to 3-chloro-1-dimethylamino-4,4-difluoro-2-(p-tolylsulfonyl)-1,3-butadiene. The feasibility of using 1-dimethylamino-2-(p-tolylsulfonyl)-polyfluoro-1-alken-3-ones in reactions with nitrogen binucleophiles has been demonstrated for the regioselective synthesis of pyrazoles and pyrimidines. The structure of 1-phenyl-4-(p-tolylsulfonyl)-5-trifluoromethyl-1H-pyrazole was confirmed by X-ray diffraction structural analysis.

Keywords

1-arylsulfonyl-1,1-dihydropolyfluoro-2-alkanone enaminone pyrazole pyrimidine Vilsmeier-Haack-Arnold reaction X-ray diffraction structural analysis 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • O. S. Kanishchev
    • 1
  • Yu. P. Bandera
    • 1
  • V. M. Timoshenko
    • 1
  • E. B. Rusanov
    • 1
  • S. A. But
    • 1
  • Yu. G. Shermolovich
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine

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