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

doi:10.1007/s10593-007-0140-8

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 journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	887-892
Number of pages	6
Journal	Chemistry of Heterocyclic Compounds
Volume	43
Issue number	7
DOIs	https://doi.org/10.1007/s10593-007-0140-8
State	Published - Jul 2007
Externally published	Yes

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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10.1007/s10593-007-0140-8

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Kanishchev, O. S., Bandera, Y. P., Timoshenko, V. M., Rusanov, E. B., But, S. A., & Shermolovich, Y. G. (2007). 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. Chemistry of Heterocyclic Compounds, 43(7), 887-892. https://doi.org/10.1007/s10593-007-0140-8

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

Research output: Contribution to journal › Article › peer-review

Kanishchev, OS, Bandera, YP, Timoshenko, VM, Rusanov, EB, But, SA & Shermolovich, YG 2007, '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', Chemistry of Heterocyclic Compounds, vol. 43, no. 7, pp. 887-892. https://doi.org/10.1007/s10593-007-0140-8

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title = "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",

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",

author = "Kanishchev, {O. S.} and Bandera, {Yu P.} and Timoshenko, {V. M.} and Rusanov, {E. B.} and But, {S. A.} and Shermolovich, {Yu G.}",

year = "2007",

month = jul,

doi = "10.1007/s10593-007-0140-8",

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T1 - 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

AU - Kanishchev, O. S.

AU - Bandera, Yu P.

AU - Timoshenko, V. M.

AU - Rusanov, E. B.

AU - But, S. A.

AU - Shermolovich, Yu G.

PY - 2007/7

Y1 - 2007/7

N2 - 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.

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.

KW - 1-arylsulfonyl-1,1-dihydropolyfluoro-2-alkanone

KW - Enaminone

KW - Pyrazole

KW - Pyrimidine

KW - Vilsmeier-Haack-Arnold reaction

KW - X-ray diffraction structural analysis

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ER -

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

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