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Updated: Sep 3, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Electrochemical collective synthesis of labeled pyrroloindoline alkaloids with Freon-type methanes as functional C1
Chao Chen1, Ru-Xin Liu1, Feng Xiong1
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of Ministry of Education, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. zhangsy16@sjtu.edu.cn.
Abstract:
Utilization of Freon-type methanes as functional one-carbon synthons in the synthesis of various deuterated indoline alkaloids was demonstrated here. A series of halomethyl radicals were generated from electro-reductive C-X cleavage of Freon-type methanes and captured efficiently by acrylamides to provide various halogenated oxindoles via radical cyclization. This reaction features good functional group tolerance, and deuterium and fluorine atoms could be introduced facilely from Freon-type methanes. Further transformation of halogenated oxindoles enabled the synthesis of many (labeled) bioactive drug molecules and skeletons, such as deuterated (±)-physostigmine, deuterated (±)-esermethole and deuterated (±)-lansai B.
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