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Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones†
Xinzhang Yu,Yu-Zhu Shang,Yu-Fei Cheng,Jun Tian,Yulan Niu,Wen-Chao Gao
Organic & Biomolecular Chemistry Pub Date : 02/17/2020 00:00:00 , DOI:10.1039/D0OB00050G
Abstract

A facile method for the synthesis of 4-chalcogenylated pyrazoles has been developed via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones. The cyclization of α,β-alkynic aldehyde hydrazones could be induced by using either sulfenyl chloride or the S-electrophiles generated in situ from the reaction of NCS and arythiol. The developed method was successfully applied to the synthesis of the sulfenyl analogue of celecoxib.

Graphical abstract: Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones
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