Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation

被引：8

作者：

Zhang, Pengbo ^{[1
]}

Li, Wenwu ^{[1
]}

Yang, Shuai ^{[1
]}

Qu, Weilong ^{[1
]}

Wang, Longyu ^{[1
]}

Lin, Jinming ^{[1
]}

Gao, Xia ^{[1
]}

机构：

[1] Xinxiang Med Univ, Sch Publ Hlth, Xinxiang 453003, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 07期

基金：

中国国家自然科学基金;

关键词：

BIOLOGICAL EVALUATION; DERIVATIVES; PHOSPHINOTHIOATES; DISCOVERY;

D O I：

10.1021/acs.joc.4c00159

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photoredox/copper-catalyzed cascade radical cyclization/phosphorothiolation reaction of N-allylbromoacetamides and P(O)SH compounds has been established. A broad range of novel nonfluorine- or difluoro-substituted 2-pyrrolidinones bearing the C(sp(3))-SP(O)(OR)(2) moiety can be conveniently constructed in moderate to good yields under mild conditions. Importantly, most of the tested phosphorothiolated 2-pyrrolidinones showed potent inhibitory effects toward both AChE and BChE.

引用

页码：4947 / 4957

页数：11

共 50 条

[1] Copper-catalyzed cascade radical cyclization of alkynoates: construction of aryldifluoromethylated coumarins
Zeng, Piaopiao
Huang, Xiaoxiao
Tang, Wei
Chen, Zhiwei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (46) : 10223 - 10227
[2] Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines
Zhang, Hong-Yu
Mao, Liu-Liang
Yang, Bin
Yang, Shang-Dong
CHEMICAL COMMUNICATIONS, 2015, 51 (19) : 4101 - 4104
[3] Enantioselective Copper-Catalyzed Construction of Aryl Pyrroloindolines via an Arylation-Cyclization Cascade
Zhu, Shaolin
MacMillan, David W. C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) : 10815 - 10818
[4] Copper-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation
Ma, Peng
Wang, Yuhang
Wang, Jianhui
Ma, Ning
NEW JOURNAL OF CHEMISTRY, 2023, 47 (19) : 9377 - 9382
[5] Synthesis of Fused-Ring Pyrrolizine Derivatives via a Copper-Catalyzed Radical Cascade Cyclization
Xu, Xiao-Bo
Hao, Li-Qiang
Liu, Xian
Wang, Yang-Yang
Yang, Zhao-Zi-Yuan
Yu, Xiao
Ding, Dong
Ji, Ya-Fei
SYNLETT, 2024, 35 (19) : 2236 - 2240
[6] Copper-catalyzed carbochlorination or carbobromination via radical cyclization of aryl amines
Ouyang, Jianing
Su, Xiaolong
Chen, Yu
Yuan, Yaofeng
Li, Yi
TETRAHEDRON LETTERS, 2016, 57 (13) : 1438 - 1441
[7] Biomimetic synthesis of (-)-chaetominine epimers via copper-catalyzed radical cyclization
Deng, Xu
Liang, Kangjiang
Tong, Xiaogang
Ding, Ming
Li, Dashan
Xia, Chengfeng
TETRAHEDRON, 2015, 71 (22) : 3699 - 3704
[8] Copper-Catalyzed 1,2-Dicarbonylative Cyclization of Alkenes with Alkyl Bromides via Radical Cascade Process
Zhao, Fengqian
Gu, Xing-Wei
Franke, Robert
Wu, Xiao-Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (49)
[9] Synthesis of δ-phosphorothiolated alcohols by photoredox/copper catalyzed remote C(sp3)-H phosphorothiolation of N-alkoxypyridinium salts
Zheng, Zhipeng
Shi, Shanshan
Ma, Qianru
Yang, Yufei
Liu, Yan
Tang, Guo
Zhao, Yufen
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6845 - 6850
[10] Copper-Catalyzed Decarboxylative Cascade Cyclization for the Synthesis of 2-Arylquinolines
Chatterjee, Rana
Pothireddy, Mohanreddy
Dandela, Rambabu
SYNLETT, 2023, 34 (09) : 1058 - 1062

← 1 2 3 4 5 →