Electrochemical synthesis of selenocyanated imidazo[1,5-a]quinolines under metal catalyst-and chemical oxidant-free conditions

被引：6

作者：

Jinjin Zhang ^{[1
]}

Huiqiao Wang ^{[1
]}

Yaru Chen ^{[1
]}

Haiquan Xie ^{[1
]}

Chenghua Ding ^{[1
]}

Jiajing Tan ^{[2
]}

Kun Xu ^{[1
,3
]}

机构：

[1] College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University

[2] Department of Organic Chemistry, Faculty of Chemistry, Beijing University of Chemical Technology

[3] College of Life Science & Bioengineering, Beijing University of Technology

来源：

Chinese Chemical Letters | 2020年 / 31卷 / 06期

基金：

中央高校基本科研业务费专项资金资助; 北京市自然科学基金; 中国国家自然科学基金; 河南省教育厅基金;

关键词：

Electrosynthesis; Organic electrochemistry; Anodic oxidation; Imidazo[1,5-a]quinoline; Selenocyanation;

D O I：

暂无

中图分类号：

O626 [杂环化合物];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is the first example of electrochemical selenocyanation of imidazo[1,5-a]quinolines with KSeCN under metal catalyst-and chemical oxidant-free conditions.This sustainable strategy shows a broad scope and great compatibility with functional groups,and affords synthetically and biologically important selenocyanated imidazo[1,5-a]quinolines in good to excellent yields with cheap graphite and Ni plates as the electrodes.The gram-scale synthesis was also successfully conducted,which might demonstrate the potential value of this electrochemical protocol.

引用

页码：1576 / 1579

页数：4

共 50 条

[41] A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions
Zhang, Xing
Wang, Chenguang
Jiang, Hong
Sun, Linhao
[J]. RSC ADVANCES, 2018, 8 (39): : 22042 - 22045
[42] Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides
Malviya, Bhanwar Kumar
Jaiswal, Pradeep K.
Verma, Ved Prakash
Badsara, Satpal Singh
Sharma, Siddharth
[J]. ORGANIC LETTERS, 2020, 22 (06) : 2323 - 2327
[43] One-Pot Synthesis of 9H-Indolo[3,2-c]pyrazolo[1,5-a]quinolines, 1H-Dipyrazolo[1,5-a:4′,3′-c]quinolines and 1H-Imidazo[4,5-c]pyrazolo[1,5-a]quinolines: Three New Heterocyclic Systems
Zhang, Yiming
Wang, Ren
Shi, Zongjun
Zhang, Wei
[J]. SYNTHESIS-STUTTGART, 2011, (11): : 1711 - 1716
[44] Synthesis of 3-alkyl substituted imidazo[1,5-a]pyridines under microwave irradiation
Wang, Lai-Bao
Pan, Jia
Tang, Can-Lin
Jiang, Da-Wei
Qiu, Fei
Bu, Xiu-Ren
Wang, Jie
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (12) : 1573 - 1576
[45] One-pot synthesis of tetrazolo[1,5-a]pyrimidines under solvent-free conditions
Ghorbani-Vaghei, Ramin
Toghraei-Semiromi, Zahra
Amiri, Mostafa
Karimi-Nami, Rahman
[J]. MOLECULAR DIVERSITY, 2013, 17 (02) : 307 - 318
[46] Regioselective synthesis of novel substituted pyrazolo[1,5-a]pyrimidines under solvent-free conditions
Quiroga, Jairo
Portilla, Jaime
Abonia, Rodrigo
Insuasty, Braulio
Nogueras, Manuel
Cobo, Justo
[J]. TETRAHEDRON LETTERS, 2008, 49 (43) : 6254 - 6256
[47] One-pot synthesis of tetrazolo[1,5-a]pyrimidines under solvent-free conditions
Ramin Ghorbani-Vaghei
Zahra Toghraei-Semiromi
Mostafa Amiri
Rahman Karimi-Nami
[J]. Molecular Diversity, 2013, 17 : 307 - 318
[48] Development of a new cascade reaction for convergent synthesis of pyrazolo[1,5-a]quinoline derivatives under transition-metal-free conditions
Kato, Jun-ya
Aoyama, Hiroshi
Yokomatsu, Tsutomu
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (07) : 1171 - 1178
[49] Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions
Zhang, Zhenlei
Yang, Jiusi
Yu, Renjie
Wu, Kairui
Bu, Jiping
Li, Shaoke
Qian, Peng
Sheng, Liangquan
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (37) : 5209 - 5212
[50] Solvent-free microwave-assisted synthesis of imidazo[1,5-a]pyridine and -quinoline derivatives
Herr, Jasmin Martha
Roessiger, Carina
Albrecht, Georg
Yanagi, Hisao
Goettlich, Richard
[J]. SYNTHETIC COMMUNICATIONS, 2019, 49 (21) : 2931 - 2940

← 1 2 3 4 5 →