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

Org Lett

College of Chemistry, Chemical Engineering, and Materials Science; Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong; Key Laboratory of Molecular and Nano Probes, Ministry of Education; Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan, 250014, P. R. China.

Published: January 2022

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.

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http://dx.doi.org/10.1021/acs.orglett.1c03693DOI Listing

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