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Chloride-incorporating cascade dearomatization of isoquinolines with chloroformate and DMAD achieving 100% atom
Zhuo-Ya Mao1,2,3, De-Xiang Yan1,2,3, Su-Fan Zhou1,2,3
1Shanxi Provincial Key Laboratory of Drug Synthesis and Novel Pharmaceutical Preparation Technology, School of Pharmacy, Shanxi Medical University, Taiyuan, Shanxi 030001, China. maozhuoya@sxmu.edu.cn.
Abstract:
A multicomponent dearomatization of isoquinolines was achieved using chloroformate and dimethyl acetylenedicarboxylate (DMAD). Distinct from conventional direct additions, this protocol proceeds via a novel cascade involving [4+2] cycloaddition and ring-opening with chloride incorporation. This method features 100% atom economy and provides direct access to 1-functionalized 1,2-dihydroisoquinolines in moderate yields with high regioselectivity.
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