Efficient synthesis of 2-arylquinazolin-4-amines via a copper-catalyzed diazidation and ring expansion cascade of 2-arylindoles

Meng-Meng Xu; Wen-Bin Cao; Xiao-Ping Xu; Shun-Jun Ji

doi:10.1039/c8cc07721e

Efficient synthesis of 2-arylquinazolin-4-amines via a copper-catalyzed diazidation and ring expansion cascade of 2-arylindoles

Chem Commun (Camb). 2018 Nov 6;54(89):12602-12605. doi: 10.1039/c8cc07721e.

Authors

Meng-Meng Xu¹, Wen-Bin Cao, Xiao-Ping Xu, Shun-Jun Ji

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, P. R. China. xuxp@suda.edu.cn shunjun@suda.edu.cn.

PMID: 30346460
DOI: 10.1039/c8cc07721e

Abstract

Copper-catalyzed synthesis of 2-arylquinazolin-4-amines from readily available 2-arylindoles and TMSN3 has been developed. The mechanism study shows that the domino reaction may involve a free radical diazidation, denitrogenation, intramolecular cyclization and ring expansion sequence.