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Copper‐Catalyzed Synthesis of 5‐Aryl‐6‐(Trifluoromethyl)‐2,3‐Dihydropyrazolo[1,2‐ a ]Pyrazol‐1(5 H )‐One
Author(s) -
Zhang Xinyu,
Wang Hui,
Xie Lili,
You Chenhui,
Han Xiaoyan,
Weng Zhiqiang
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202100693
Subject(s) - trifluoromethyl , aromatization , chemistry , aryl , catalysis , nucleophile , cycloaddition , medicinal chemistry , combinatorial chemistry , copper , nucleophilic substitution , functional group , organic chemistry , stereochemistry , alkyl , polymer
An efficient protocol for the synthesis of 5‐aryl‐6‐(trifluoromethyl)‐2,3‐dihydropyrazolo[1,2‐ a ]pyrazol‐1(5 H )‐one derivatives through a copper‐catalyzed [3+2]‐cycloaddition of azomethine imines with 3,3,3‐trifluoropropyne (generated in situ from dehydrobromination of 2‐bromo‐3,3,3‐trifluoropropene under base conditions) is developed. The advantages of this transformation are the broad substrate scope and the good functional group compatibility. The subsequent oxidation and nucleophilic substitution/aromatization provide a new approach to 4‐trifluoromethylated pyrazol‐1‐yl propanoic acids.