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Multigram Synthesis of Fluoroalkyl‐Substituted Pyrazole‐4‐carboxylic Acids
Author(s) -
Iminov Rustam T.,
Mashkov Alexander V.,
Vyzir Ivan I.,
Chalyk Bohdan A.,
Tverdokhlebov Anton V.,
Mykhailiuk Pavel K.,
Babichenko Ludmila N.,
Tolmachev Andrey A.,
Volovenko Yulian M.,
Biitseva Angelina,
Shishkin Oleg V.,
Shishkina Svetlana V.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403295
Subject(s) - chemistry , enamine , pyrazole , acylation , organic chemistry , acetic acid , carbon atom , alkyl , carboxylic acid , acetic anhydride , medicinal chemistry , catalysis
Acylation of tert ‐butyl 3‐(methylamino)but‐2‐enoate with fluorinated acetic acid anhydrides occurred at the enamine carbon atom. The reaction of the resulting tert ‐butyl 3‐(methylamino)‐2‐(R F CO)but‐2‐enoates with alkyl hydrazines resulted in mixtures of isomeric pyrazoles that were easily separated by column chromatography. The target fluorinated pyrazole‐4‐carboxylic acids were obtained on a multigram scale.