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The reaction of aryl and heteroarylhydrazines with aryl-trifluoromethyl β-diketones

✍ Scribed by Shiv P. Singh; Vinod Kumar; Ranjana Aggarwal; Jose Elguero


Book ID
102892024
Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
616 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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We report the results obtained when five aromatic or heteroaromatic hydrazines react with six β‐diketones bearing trifluoromethyl and aryl substituents. Forty‐two compounds have been isolated corresponding to two isomeric trifluoromethyl pyrazoles and the intermediate 5‐CF~3~, 5‐OH pyrazolines. The results have provided useful information for establishing the mechanism of the synthesis of pyrazoles.


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b,b-Diphenyl-a-(trifluoromethyl)vinylstannane 6 was prepared in good yield via several steps from 2,3,3,3-tetrafluoro-1-phenyl-1-phenylthiopropene. The cross-coupling reactions of 6 with aryl iodides in the presence of a catalytic amount of Pd(PPh 3 ) 4 and CuI provided trifluoromethylated triphenyl