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Updated: Nov 20, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
Xinxin Lin1, Cuilian Zeng1, Chengkou Liu1
1College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, China. fzcpu@njtech.edu.cn.
Abstract:
An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale up can be achieved conveniently with higher productivity. Moreover, this method has good position-control, and water and air tolerance. Costly quaternary ammonium salts were avoided. Radical-trapping, H/D exchange, KIE and cyclic voltammetry experiments were conducted to gain insight into the reaction mechanism.
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