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

Research output: Contribution to journalArticle

11 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)887-892
Number of pages6
JournalChemistry of Heterocyclic Compounds
Volume43
Issue number7
DOIs
StatePublished - Jul 1 2007

Keywords

  • 1-arylsulfonyl-1,1-dihydropolyfluoro-2-alkanone
  • Enaminone
  • Pyrazole
  • Pyrimidine
  • Vilsmeier-Haack-Arnold reaction
  • X-ray diffraction structural analysis

ASJC Scopus subject areas

  • Organic Chemistry

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