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Chemoselective Trimerization of Isocyanides: De Novo Synthesis of 2-Indole-Substituted Quinolines and Pyridines

Lan Bao, Yu Liu, Jinghan Peng, Yuan Wang, Jinhuan Dong, Xianxiu Xu

2021Organic Letters22 citationsDOI

Abstract

A catalyst-free chemoselective trimerization reaction of readily available isocyanides is described. This domino reaction provides facile access to a wide range of 2-(indol-2-yl)-quinolines and 2-(indol-2-yl)-pyridines in moderate to excellent yields. A "head to head" heterodimerization of two isocyanides is proposed as the key step of this reaction.

Topics & Concepts

ChemistryIndole testIsocyanideDominoCatalysisCombinatorial chemistryCascade reactionReaction conditionsOrganic chemistryMulticomponent Synthesis of HeterocyclesCatalytic C–H Functionalization MethodsSynthesis of heterocyclic compounds
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