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Updated: Aug 26, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
TsCl-promoted thiolation of quinoline N-oxides with thiophenols
Chengxian Hu1, Ruikai Liu1, Zhitao Ning1
1Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China. fu_ying@126.com.
Abstract:
A metal-free method for the regioselective synthesis of 2-thiolated quinolines from quinoline N-oxides in water at room temperature is developed. The reaction is conducted using benzenethiols as thiolation reagents in the presence of p-toluenesulfonyl chloride via p-toluenesulfonyl chloride-assisted tandem C-H bond activation, nucleophilic addition, deoxygenation and aromatization processes. This method does not require the use of metal catalysts and oxidants. It shows the advantages of wide functional group tolerance, short reaction times and simple operation.
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