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, Sergii Buth, Yu G. Shermolovich

Research output: Contribution to journalArticle

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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 2007
Externally publishedYes

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Pyrazoles
Pyrimidines
Acetone
Hydrates
Structural analysis
Nitrogen
X ray diffraction

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

Cite this

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. / Kanishchev, O. S.; Bandera, Yu P.; Timoshenko, V. M.; Rusanov, E. B.; Buth, Sergii; Shermolovich, Yu G.

In: Chemistry of Heterocyclic Compounds, Vol. 43, No. 7, 07.2007, p. 887-892.

Research output: Contribution to journalArticle

Kanishchev, O. S. ; Bandera, Yu P. ; Timoshenko, V. M. ; Rusanov, E. B. ; Buth, Sergii ; Shermolovich, Yu G. / 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. In: Chemistry of Heterocyclic Compounds. 2007 ; Vol. 43, No. 7. pp. 887-892.
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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.",
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AU - Kanishchev, O. S.

AU - Bandera, Yu P.

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AB - 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.

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