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

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

doi:10.1021/acs.joc.9b00755

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

J Org Chem. 2019 May 17;84(10):6395-6404. doi: 10.1021/acs.joc.9b00755. Epub 2019 Apr 30.

Authors

Jing Qian¹, Zhenwei Lin¹, Zaibin Wang¹, Zhixing Peng¹, Li Wu¹, Ping Lu¹, Yanguang Wang¹

Affiliation

¹ Department of Chemistry , Zhejiang University , Hangzhou 310027 , P. R. China.

PMID: 30999741
DOI: 10.1021/acs.joc.9b00755

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.