New synthetic access to 3-fluoroalky1-5-pyrazolecarboxylates and carboxylic acids

A novel process for preparing 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids is hereby presented. Easily accesible alpha-fluorinated ketimines were condensed with oxalyl monochloride derivatives, and the obtained vinamides underwent acid-catalyzed cyclization with substituted hydrazines....

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Bibliographic Details
Published inJournal of fluorine chemistry Vol. 214; pp. 17 - 23
Main Authors Herrera, Alberto Gomez, Schmitt, Etienne, Panossian, Armen, Vors, Jean-Pierre, Pazenok, Sergii, Leroux, Frederic R.
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier 01.10.2018
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
TEBUFENPYRAD
Vinamide
CYCLOADDITION
Cyclization
3,5-disubstitution
SUBSTITUTED PYRAZOLES
REACTIVITY
ALKYNES
Fluorinated pyrazole
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Summary:A novel process for preparing 3-fluoroalkyl-5-pyrazolecarboxylates and carboxylic acids is hereby presented. Easily accesible alpha-fluorinated ketimines were condensed with oxalyl monochloride derivatives, and the obtained vinamides underwent acid-catalyzed cyclization with substituted hydrazines. This highly efficient protocol can also be used for non-fluorinated C-3 and C-5 substituents.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2018.07.010