Visible light-mediated ring opening and cyclization of aryl cyclopropanes: efficient synthesis of pyrrolo[1,2-a]quinoxalin-4(5H)-ones with antineoplastic activity

被引：19

作者：

Shen, Jiabin ^{[1
,2
]}

Yang, Yong ^{[1
]}

Chen, Chao ^{[1
]}

Xu, Hao ^{[1
]}

Shen, Chao ^{[1
]}

Zhang, Pengfei ^{[2
]}

机构：

[1] Zhejiang Shuren Univ, Key Lab Pollut Exposure & Hlth Intervent Zhejiang, Key Lab Pollut Exposure & Hlth Intervent Zhejiang, Hangzhou 310015, Peoples R China

[2] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 06期

基金：

中国国家自然科学基金;

关键词：

COPPER-CATALYZED ANNULATION; UNACTIVATED ALKENES; CASCADE REACTION; DERIVATIVES; METAL; QUINOXALIN-2(1H)-ONES; 2-FORMYLAZOLES; INHIBITORS; SAR;

D O I：

10.1039/d3qo02100a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the visible light-mediated synthesis of pyrrolo[1,2-a]quinoxalin-4(5H)-ones from aryl cyclopropanes, quinoxalinones, hydrochloric acid, and nitric acid through ring opening and unexpected cyclization. This operationally simple and catalyst-free methodology opens a green and efficient approach for the synthesis of pyrrolo[1,2-a]quinoxalin-4(5H)-ones possessing good antineoplastic activity using cheap standard laboratory reagents, and the scalability of the developed protocol is further demonstrated by a gram-scale synthesis and in vitro cytotoxicity assay.

引用

收藏

页码：1758 / 1764

页数：7

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