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Studies on isoxazole and pyrazole formation by the reaction of trifluoromethyl-substituted anilines with oxime and hydrazone dianions

✍ Scribed by Lucjan Strekowski; Shou-Yuan Lin


Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
211 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

5‐(2‐Aminophenyl)isoxazoles are obtained in good yields by the reaction of 2‐(trifluoromethyl)aniline with dilithio derivatives of oximes of acetone, 3‐pentanone, propiophenone, and cyclohexanone. An analogous synthesis of a substituted isoxazole from 4‐(trifluoromethyl)aniline and 3‐pentanone oxime and the synthesis of a substituted pyrazole from 2‐(trifluoromethyl)aniline and 3‐pentanone hydrazone are less efficient.


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## Abstract The 1__H__‐pyrazole‐3‐carboxylic acid **2**, obtained from the furan‐2,3‐dione **1** and __N__‐Benzylidene‐__N__'‐(3‐nitrophenyl) hydrazine, was converted via reactions of its acid chloride **3** with various alcohols or N‐nucleo‐philes into the corresponding ester or amide derivatives