Synthesis of fluorinated oxazoles by oxidative cyclization of fluorinated enamides

[Display omitted] •Fluorinated isoxazoles were obtained by oxidation of the corresponding enamides.•These fluorinated building blocks are useful for Drug discovery and Agrochemistry.•Di- and trifluoromethyl-containing compounds were obtained. Novel approach to CF3-/CHF2-oxazoles was developed. The k...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2017-04, Vol.196, p.88-97
Main Authors: Shishlyk, Oleg S., Shcherbatiuk, Andrey V., Iminov, Rustam T., Tverdokhlebov, Anton V., Tolmachev, Andrey A., Mykhailiuk, Pavel K., Biitseva, Angelina V.
Format: Article
Language:English
Subjects:
Acylation
Chemical synthesis
Fluorination
Fluorine
Fluoroalkyl
Hypervalent iodine
Oxazole
Oxazoles
Oxidation
Ring closure
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Summary:[Display omitted] •Fluorinated isoxazoles were obtained by oxidation of the corresponding enamides.•These fluorinated building blocks are useful for Drug discovery and Agrochemistry.•Di- and trifluoromethyl-containing compounds were obtained. Novel approach to CF3-/CHF2-oxazoles was developed. The key reaction was oxidation of fluoroalkyl enamides with PhI(RCO2)2.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2016.09.014