Pd-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones: synthesis of fluorescent indazolo[3,2-b]quinazolinones

Weiguang Yang; Jiuxi Chen; Xiaobo Huang; Jinchang Ding; Miaochang Liu; Huayue Wu

doi:10.1021/ol5026553

Pd-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones: synthesis of fluorescent indazolo[3,2-b]quinazolinones

Org Lett. 2014 Oct 17;16(20):5418-21. doi: 10.1021/ol5026553. Epub 2014 Oct 7.

Authors

Weiguang Yang¹, Jiuxi Chen, Xiaobo Huang, Jinchang Ding, Miaochang Liu, Huayue Wu

Affiliation

¹ College of Chemistry & Materials Engineering, Wenzhou University , Wenzhou, Zhejiang 325035, P. R. China.

PMID: 25290066
DOI: 10.1021/ol5026553

Abstract

A palladium-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade "rollover" cyclometalation and C-H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.