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

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.

Automated summary

The catalyst-free chemoselective trimerization reaction of isocyanides leads to the formation of a wide range of 2-(indol-2-yl)-quinolines and 2-(indol-2-yl)-pyridines in moderate to excellent yields. The key step of this reaction is proposed to be the head to head heterodimerization of two isocyanides.