posted on 2021-12-07, 17:05authored byChen Cai, Yi Lu, Chengcheng Yuan, Zheng Fang, Xiaobing Yang, Chengkou Liu, Kai Guo
A straightforward
one-pot two-step electrosynthesis of cinnoline
derivatives from ortho-alkynyl acetophenones and
sulfonyl hydrazides has been developed through the organocatalytic
cascade radical cyclization and migration. This methodology features
green and mild reaction conditions, good to excellent yield, broad
functional group tolerance, excellent regioselectivity, and use of
readily available substrates. Moreover, based on isotope labeling,
radical trapping, singlet oxygen and superoxide radical anion inhibiting,
cyclic voltammetry, and EPR experiments, a possible electrochemically
cascade radical cyclization and migration process was proposed.