Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3083-3088.DOI: 10.6023/cjoc202104047 Previous Articles     Next Articles

ARTICLES

可见光诱导的2-(苄基氨基)苯甲酰胺合成4(3H)-喹唑啉酮

李鑫昌a, 杨惠茹a, 胡浙耀a, 金鑫b, 张文一c, 郭勋祥a,d,*()   

  1. a 上海交通大学系统生物医学研究院 系统生物医学教育部重点实验室 上海 200240
    b 上海交通大学化学化工学院 上海 200240
    c 上海交通大学医学院附属同仁医院 上海 200336
    d 上海市手性药物分子工程重点实验室 上海 200240
  • 收稿日期:2021-04-21 修回日期:2021-04-30 发布日期:2021-05-08
  • 通讯作者: 郭勋祥
  • 基金资助:
    上海市科学技术委员会(18JC1410801); 上海交通大学医工交叉基金(YG2019QNA38)

Synthesis of 4(3H)-Quinazolinones by Visible-Light-Induced 2-Benzylaminobenzamides

Xinchang Lia, Huiru Yanga, Zheyao Hua, Xin Jinb, Wenyi Zhangc, Xunxiang Guoa,d()   

  1. a Key Laboratory of Systems Biomedicine (Ministry of Education), Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Shanghai 200240
    b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
    c Tongren Hospital, School of Medicine Shanghai Jiao Tong University, Shanghai 200336
    d Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai 200240
  • Received:2021-04-21 Revised:2021-04-30 Published:2021-05-08
  • Contact: Xunxiang Guo
  • Supported by:
    Science and Technology Commission of Shanghai Municipality(18JC1410801); Medical Engineering Cross Fund of Shanghai Jiao Tong University(YG2019QNA38)

An environmental benign protocol of visible-light-induced reaction has been developed. The methodology allows effective synthesis of 4(3H)-quinazolinones from 2-benzylaminobenzamides in simple and mild reaction conditions. Just irradiation with a blue LED light at room temperature, the reaction proceeds well to provide the corresponding quinazolinones in good to high yields under metal-free, photocatalyst-free and mediator-free conditions. This protocol is demonstrated by its wide substrate scope, good functional group tolerance, operationally simple, and gram-scale reaction. Mechanism studies suggest that a radical pathway might be involved in current reaction.

Key words: visible-light, 2-benzylaminobenzamides, 4(3H)-quinazolinones