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Synthesis of 3-amino-4-fluoropyrazoles

(2011) JOURNAL OF ORGANIC CHEMISTRY. 76(10). p.4105-4111
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Abstract
Fluorinated pyrazoles bearing additional functional groups that allow further functionalization are of considerable interest as building blocks in medicinal chemistry. The developed synthetic strategy for new 3-amino-4-fluoropyrazoles consists of a monofluorination of β-methylthio- β-enaminoketones using 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2] octane bis(tetrafluoroborate) (Selectfluor) toward the corresponding monofluorinated enaminoketones, followed by condensation with different hydrazines.
Keywords
PYRAZOLE FORMATION, FLUORINATED TEBUFENPYRAD ANALOGS, ALPHA, HETEROCYCLES, CHEMISTRY, DITHIOACETALS, S, N-ACETALS, INHIBITORS, REAGENTS, KETONES

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Citation

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MLA
Surmont, Riccardo, et al. “Synthesis of 3-Amino-4-Fluoropyrazoles.” JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 10, 2011, pp. 4105–11, doi:10.1021/jo2000989.
APA
Surmont, R., Verniest, G., De Schrijver, M., Thuring, J. W., ten Holte, P., Deroose, F., & De Kimpe, N. (2011). Synthesis of 3-amino-4-fluoropyrazoles. JOURNAL OF ORGANIC CHEMISTRY, 76(10), 4105–4111. https://doi.org/10.1021/jo2000989
Chicago author-date
Surmont, Riccardo, Guido Verniest, Mathias De Schrijver, Jan Willem Thuring, Peter ten Holte, Frederik Deroose, and Norbert De Kimpe. 2011. “Synthesis of 3-Amino-4-Fluoropyrazoles.” JOURNAL OF ORGANIC CHEMISTRY 76 (10): 4105–11. https://doi.org/10.1021/jo2000989.
Chicago author-date (all authors)
Surmont, Riccardo, Guido Verniest, Mathias De Schrijver, Jan Willem Thuring, Peter ten Holte, Frederik Deroose, and Norbert De Kimpe. 2011. “Synthesis of 3-Amino-4-Fluoropyrazoles.” JOURNAL OF ORGANIC CHEMISTRY 76 (10): 4105–4111. doi:10.1021/jo2000989.
Vancouver
1.
Surmont R, Verniest G, De Schrijver M, Thuring JW, ten Holte P, Deroose F, et al. Synthesis of 3-amino-4-fluoropyrazoles. JOURNAL OF ORGANIC CHEMISTRY. 2011;76(10):4105–11.
IEEE
[1]
R. Surmont et al., “Synthesis of 3-amino-4-fluoropyrazoles,” JOURNAL OF ORGANIC CHEMISTRY, vol. 76, no. 10, pp. 4105–4111, 2011.
@article{1904050,
  abstract     = {{Fluorinated pyrazoles bearing additional functional groups that allow further functionalization are of considerable interest as building blocks in medicinal chemistry. The developed synthetic strategy for new 3-amino-4-fluoropyrazoles consists of a monofluorination of β-methylthio- β-enaminoketones using 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2] octane bis(tetrafluoroborate) (Selectfluor) toward the corresponding monofluorinated enaminoketones, followed by condensation with different hydrazines.}},
  author       = {{Surmont, Riccardo and Verniest, Guido and De Schrijver, Mathias and Thuring, Jan Willem and ten Holte, Peter and Deroose, Frederik and De Kimpe, Norbert}},
  issn         = {{0022-3263}},
  journal      = {{JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{PYRAZOLE FORMATION,FLUORINATED TEBUFENPYRAD ANALOGS,ALPHA,HETEROCYCLES,CHEMISTRY,DITHIOACETALS,S,N-ACETALS,INHIBITORS,REAGENTS,KETONES}},
  language     = {{eng}},
  number       = {{10}},
  pages        = {{4105--4111}},
  title        = {{Synthesis of 3-amino-4-fluoropyrazoles}},
  url          = {{http://dx.doi.org/10.1021/jo2000989}},
  volume       = {{76}},
  year         = {{2011}},
}

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