文献类型：期刊文献

英文题名：Light-Driven Intramolecular C-N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

作者：Jing, Dong[1];Lu, Cong[1];Chen, Zhuo[2];Jin, Songyang[1];Xie, Lijuan[1];Meng, Ziyi[1];Su, Zhishan[1];Zheng, Ke[1]

机构：[1]Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Sichuan, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China

年份：2019

卷号：58

期号：41

起止页码：14666

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20193607400468);WOS:【SCI-EXPANDED(收录号:WOS:000484125200001)，CCR-EXPANDED(收录号:WOS:000484125200001)】；

基金：We thank the National Natural Science Foundation of China (Nos. 21602142), and Fundamental Research Funds for the Central Universities. We thank the Xiaoming Feng laboratory (SCU) for access to equipment. We also thank the comprehensive training platform of the Specialized Laboratory in the College of Chemistry at Sichuan University for compound testing. We appreciate valuable suggesttions from Prof. J. Chruma (Sichuan University).

语种：英文

外文关键词：cross-coupling; heterocycles; photochemistry; reaction mechanisms; synthetic methods

摘要：Reported herein is a visible-light-driven intramolecular C-N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.