SYNTHESIS OF 5-POLYFLUOROALKYL-4-(<i>p</i>-TOLYLSULFONYL)PYRAZOLES AND 4-POLYFLUOROALKYL-5-(<i>p</i>-TOLYLSULFONYL)PYRIMIDINES FROM 1-DIMETHYLAMINO-2-(<i>p</i>-TOLYLSULFONYL)POLYFLUORO-1-ALKEN-3-ONES

Authors

  • А. С. Канищев Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 01094 Kiev
  • Ю. П. Бандера Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 01094 Kiev
  • В. М. Тимошенко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 01094 Kiev
  • Э. Б. Русанов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 01094 Kiev
  • С. А. Бут Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 01094 Kiev
  • Ю. Г. Шермолович Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 01094 Kiev

DOI:

https://doi.org/10.1007/7451

Keywords:

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

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-penta-none 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.

How to Cite
Kanishchev, O. S.; Bandera, Yu. P.; Timoshenko, V. M.; Rusanov, E. B.; But, S. A.; Shermolovich, Yu. G.  Chem. Heterocycl. Compd. 2007, 43, 887. [Khim. Geterotsikl. Soedin. 2007, 1052.]

For this article in the English edition see DOI 10.1007/s10593-007-0140-8


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Published

2023-02-13

Issue

No. 7 (2007)

Section

Original Papers