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

Qian, Jing; Lin, Zhenwei; Wang, Zaibin; Peng, Zhixing; Wu, Li; Lu, Ping; Wang, Yanguang

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

2019

The Cu(II)-catalyzed electrophilic cyclization reaction between o-hydroxyarylenaminones and 3-diazoindolin-2-imines furnished 3-indolyl-4H-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.

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