A visible light mediated, metal and oxidant free highly efficient cross dehydrogenative coupling (CDC) reaction between quinoxalin-2(1H)-ones and ethers

被引:52
作者
Mane, Kishor D. [1 ,2 ]
Kamble, Rohit B. [1 ,2 ]
Suryavanshi, Gurunath [1 ,2 ]
机构
[1] CSIR, Natl Chem Lab, Chem Engn & Proc Dev Div, Pune 411008, Maharashtra, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
关键词
C-C; AMINATION REACTIONS; BOND FORMATIONS; FUNCTIONALIZATION; ARYLATION; DESIGN; QUINOXALIN-2(H)-ONES; ACTIVATION; INHIBITORS; OXIDATION;
D O I
10.1039/c9nj00075e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The efficient and metal free, white light mediated 3C alkylation of quinoxalin-2(1H)-ones via a cross dehydrogenative coupling reaction with cyclic ethers using eosin Y as a photocatalyst is described. This reaction has broad substrate scope and strong functional group tolerance with good to excellent yields.
引用
收藏
页码:7403 / 7408
页数:6
相关论文
共 56 条
[1]   Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine [J].
Ajani, Olayinka Oyewale .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 :688-715
[2]   Visible-light-induced C(sp3)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions [J].
Akula, Pavan Sudheer ;
Hong, Bor-Cherng ;
Lee, Gene-Hsiang .
RSC ADVANCES, 2018, 8 (35) :19580-19584
[3]   Metal-free hypervalent iodine/TEMPO mediated oxidation of amines and mechanistic insight into the reaction pathways [J].
Bansode, Ajay H. ;
Suryavanshi, Gurunath .
RSC ADVANCES, 2018, 8 (56) :32055-32062
[4]   Evaluation of masseter muscle morphology in different types of malocclusions using cone beam computed tomography [J].
Becht, Michael P. ;
Mah, James ;
Martin, Chris ;
Razmus, Thomas ;
Gunel, Erdogan ;
Ngan, Peter .
INTERNATIONAL ORTHODONTICS, 2014, 12 (01) :32-48
[5]   Design for carbon-carbon bond forming reactions under ambient conditions [J].
Brahmachari, Goutam .
RSC ADVANCES, 2016, 6 (69) :64676-64725
[6]   Metal-free annulation of β-acylamino ketones: facile access to spirooxazolines and oxazolines via oxidative C-O bond formation [J].
Chavan, Santosh S. ;
Rupanawar, Bapurao D. ;
Kamble, Rohit B. ;
Shelke, Anil M. ;
Suryavanshi, Gurunath .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04) :544-548
[7]   Synthesis and antimicrobial activity of novel quinazolinone-thiazolidine-quinoline compounds [J].
Desai, N. C. ;
Dodiya, Amit ;
Shihory, Niraj .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2013, 17 (03) :259-267
[8]   Visible light-promoted C-H functionalization of ethers and electron-deficient arenes [J].
Devari, Shekaraiah ;
Shah, Bhahwal Ali .
CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1490-1493
[9]   Eosin Y as a Direct Hydrogen-Atom Transfer Photocatalyst for the Functionalization of C-H Bonds [J].
Fan, Xuan-Zi ;
Rong, Jia-Wei ;
Wu, Hao-Lin ;
Zhou, Quan ;
Deng, Hong-Ping ;
Da Tan, Jin ;
Xue, Cheng-Wen ;
Wu, Li-Zhu ;
Tao, Hai-Rong ;
Wu, Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (28) :8514-8518
[10]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100