Visible-Light-Driven Synthesis of Ester-Substituted Imidazole-Fused Heterocycles via Tandem Radical Cyclization

被引:0
作者
Yan, Qian [1 ,2 ]
Zhang, Mai [1 ,2 ]
Yao, Jie [1 ,2 ]
Zhuang, Zi-Han [1 ,2 ]
Chen, Shi-Hua [1 ,2 ]
Yang, Shi-Hai [1 ,2 ]
Li, Zhi-Wei [1 ,2 ]
Li, Jiang-Sheng [1 ,2 ]
机构
[1] Changsha Univ Sci & Technol, Sch Chem & Pharmaceut Engn, Hunan Prov Key Lab Mat Protect Elect Power & Trans, Changsha 410114, Peoples R China
[2] Changsha Univ Sci & Technol, Sch Chem & Pharmaceut Engn, Hunan Prov Key Lab Cytochem, Changsha 410114, Peoples R China
关键词
Alkenes; Cascade cyclization; Nitrogen heterocycles; Photocatalysis; Radical reactions; ACCESS;
D O I
10.1002/ajoc.202500479
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel tandem radical cyclization strategy is reported for the efficient synthesis of ester-functionalized imidazole-fused heterocycles. This method leverages visible-light photocatalysis and modular substrate design to achieve high regioselectivity and atom economy. The protocol demonstrates broad compatibility with diverse N-allylimidazoles and bromoacetates, enabling rapid construction of structurally complex products under mild conditions.
引用
收藏
页数:6
相关论文
共 50 条
[1]   Quantitative structure-metabolism relationships: Steric and nonsteric effects in the enzymatic hydrolysis of noncongener carboxylic esters [J].
Buchwald, P ;
Bodor, N .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (25) :5160-5168
[2]   Alkoxycarbonylation-triggered nitrile insertion/remote C(sp2)-H and C(sp3)-H functionalization to access esterified quinazolinones and amidines [J].
Cai, Shao-Qun ;
Xiao, Hui-Xin ;
Fang, Shi-Cui ;
Li, Pan-Pan ;
Yang, Zhi ;
Liang, Wu ;
Pan, Bin ;
Du, Fei .
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (14) :3861-3867
[3]   Synthesis of ester-containing phenanthridines via photoredox-catalyzed radical cascade cyclization of N-arylacrylamides with alkyloxalyl chlorides [J].
Chen, Meiling ;
Chen, Jian-Qiang ;
Chen, Zhengkai ;
Wu, Jie .
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (16) :3995-4001
[4]   Highly Substituted Lactone/Ester-Containing Furan Library by the Palladium-Catalyzed Carbonylation of Hydroxyl-Substituted 3-lodofurans [J].
Cho, Chul-Hee ;
Larock, Richard C. .
ACS COMBINATORIAL SCIENCE, 2011, 13 (03) :272-279
[5]   Photoredox-catalyzed cascade addition/cyclization of N-propargyl aromatic amines: access to 3-difluoroacetylated or 3-fluoroacetylated quinolines [J].
Deng, Qinfei ;
Xu, Yan ;
Liu, Ping ;
Tan, Liping ;
Sun, Peipei .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (01) :19-23
[6]   Photoinduced diversity-oriented synthesis of α-ketoester β-enamino esters, 3,3-difluoro-4-pyrrolin-2-ones, and 3-fluoro-3-pyrrolin-2-ones from bromodifluoroacetates and β-enamino esters [J].
Feng, Dewei ;
Zheng, Renhua ;
Li, Zhifang ;
Geng, Xiao ;
Wang, Lei .
ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (15) :4305-4310
[7]   Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1 H )-ones using water as the hydrogen donor [J].
Feng, Qiang ;
Hao, Jindong ;
Hu, Ya ;
Fu, Rong ;
Wei, Wei ;
Yi, Dong .
CHINESE CHEMICAL LETTERS, 2025, 36 (06)
[8]   Halogen-Bonding-Promoted C-H Malonylation of Indoles under Visible-Light Irradiation [J].
Gao, Xuebo ;
Chang, Rong ;
Rao, Junxin ;
Hao, Danyang ;
Zhang, Zhuxia ;
Zhou, Cong-Ying ;
Guo, Zhen .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12) :8198-8202
[9]   Convenient Access to Ester-Containing Quinolinones through a Sequential Radical Alkoxycarbonylation/Cyclization/Hydrolysis Process [J].
Guo, Sa ;
Wang, Xin ;
Zhao, Dongyang ;
Zhang, Zhiguo ;
Zhang, Guisheng ;
Tang, Shi ;
Sun, Kai .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (02)
[10]   Visible-Light-Driven Synthesis of 6-Aroyl Benzimidazo[1,2-c]quinazolines from N-Cyanobenzimidazoles and α-Keto Acids by Radical Relay Cyclization [J].
Hu, Yang ;
Liu, Cheng-Liang ;
He, Wen-Tao ;
Liu, Li-Hong ;
Li, Jiang-Sheng ;
Li, Zhi-Wei ;
Liu, Han-Wen ;
Li, Wen-Sheng .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (34)