Issue 9, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
09 Jan 2020
Accepted
17 Feb 2020
First published
17 Feb 2020

Org. Biomol. Chem., 2020,18, 1806-1811

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

X. Yu, Y. Shang, Y. Cheng, J. Tian, Y. Niu and W. Gao, Org. Biomol. Chem., 2020, 18, 1806 DOI: 10.1039/D0OB00050G

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