1338378-17-8Relevant articles and documents
DMF-catalyzed direct and regioselective C-H functionalization: Electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles
Liu, Yuanyuan,He, Guangke,Chen, Kai,Jin, Yin,Li, Yufeng,Zhu, Hongjun
, p. 5323 - 5330 (2011/11/13)
A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I -, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series. A novel DMF-catalyzed electrophilic/nucleophilic 4-halogenation of 3-oxypyrazole derivatives has been developed. This halogenation procedure provides quick access to many novel 4-halo-3-oxypyrazole series.