Copper-Carbene-Triggered Electrophilic Cyclization of o-Hydroxyarylenaminones with 3-Diazoindolin-2-imines: Synthesis of 3-Indolyl-4 H-chromen-4-ones and Pyrido[2,3- b:6,5- b']diindoles.

Abstract

The Cu(II)-catalyzed electrophilic cyclization reaction between o-hydroxyarylenaminones and 3-diazoindolin-2-imines furnished 3-indolyl-4 H-chromen-4-ones in moderate to good yields with a broad substrate scope. Several pyrido[2,3- b:6,5- b']diindoles and one pyrazino[2,3- b:5,6- b']diindole were also obtained as byproducts in some cases and tested for their photophysical properties. Pyrido[2,3- b:6,5- b']diindoles exhibited solvent-dependent emission, while pyrazino[2,3- b:5,6- b']diindole emitted strong luminescence with 25.6% quantum yield in cyclohexane.