Direct cross-dehydrogenative coupling reactions of imidazopyridines and 1-naphthylamines with ethers under metal-free conditions

被引:3
作者
Dong, Zhe [1 ,2 ]
Liu, Yu [3 ]
Zhou, Chen-Wei [3 ]
Huang, Jun-Jian [3 ]
Guo, Tao [3 ]
Wang, Yun [1 ]
机构
[1] Beijing Univ Chinese Med, Sch Chinese Mat Med, Beijing 100029, Peoples R China
[2] Natl Inst Food & Drug Control, Inst Food Control, Beijing, Peoples R China
[3] Henan Univ Technol, Sch Chem & Chem Engn, Zhengzhou 450052, Peoples R China
关键词
Cross-dehydrogenative coupling; ethers; imidazopyridines; metal-free; 1-naphthylamines; C-H BONDS; DIRECT ALPHA-ARYLATION; ONE-POT SYNTHESIS; SULFUR/SELENIUM POWDER; FUNCTIONALIZATION; IMIDAZOHETEROCYCLES; DERIVATIVES; ALKYLATION; QUINOXALIN-2(1H)-ONES; CHALCOGENATION;
D O I
10.1080/00397911.2020.1761394
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Convenient, efficient metal-free direct cross-dehydrogenative coupling reactions of imidazopyridines and 1-naphthylamines with ethers were developed. This procedure provided a wide range of valuable, structurally diverse 3-alkyl-imidazopyridine and 4-alkyl-1-naphthylamine derivatives in moderate-to-good yields and with good functional group tolerance.
引用
收藏
页码:1972 / 1981
页数:10
相关论文
共 72 条
[31]   Transition-Metal-Free TBAI-Facilitated Addition-Cyclization of N-Methyl-N-arylacrylamides with Arylaldehydes or Benzenesulfonohydrazides: Access to Carbonyl- and Sulfone-Containing N-Methyloxindoles [J].
Ji, Peng-Yi ;
Zhang, Ming-Zhong ;
Xu, Jing-Wen ;
Liu, Yu-Feng ;
Guo, Can-Cheng .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12) :5181-5189
[32]   Highly Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via Organocatalytic Michael/Aza-Henry Tandem Reactions [J].
Jia, Zhen-Xin ;
Luo, Yong-Chun ;
Xu, Peng-Fei .
ORGANIC LETTERS, 2011, 13 (05) :832-835
[33]   Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated C-H Functionalization and the Minisci Reaction [J].
Jin, Jian ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1565-1569
[34]   Nickel-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Inactive C(sp3)-H Bonds with Indole Derivatives [J].
Jin, Li-Kun ;
Wan, Li ;
Feng, Jie ;
Cai, Chun .
ORGANIC LETTERS, 2015, 17 (19) :4726-4729
[35]   Copper-Catalyzed C4-H Regioselective Phosphorylation/Trifluoromethylation of Free 1-Naphthylamines [J].
Jing, Chunfeng ;
Chen, Xiaolan ;
Sun, Kai ;
Yang, Yongkang ;
Chen, Tong ;
Liu, Yan ;
Qu, Lingbo ;
Zhao, Yufen ;
Yu, Bing .
ORGANIC LETTERS, 2019, 21 (02) :486-489
[36]   Oxidative Cross-Coupling of sp3- and sp2-Hybridized C-H Bonds: Vanadium-Catalyzed Aminomethylation of Imidazo[1,2-a]pyridines [J].
Kaswan, Pinku ;
Porter, Ashley ;
Pericherla, Kasiviswanadharaju ;
Simone, Marissa ;
Peters, Sean ;
Kumar, Anil ;
DeBoef, Brenton .
ORGANIC LETTERS, 2015, 17 (21) :5208-5211
[37]   Regioselective Copper-Catalyzed Oxidative Cross-Coupling of Imidazo[1,2-a] pyridines with Methyl Ketones: An Efficient Route for Synthesis of 1,2-Diketones [J].
Lei, Sai ;
Chen, GuiJun ;
Mai, Yingying ;
Chen, Longbin ;
Cai, Huiyin ;
Tan, Jingwen ;
Cao, Hua .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) :67-73
[38]   Copper-catalysed oxidative C-H/C-H coupling between olefins and simple ethers [J].
Liu, Dong ;
Liu, Chao ;
Li, Heng ;
Lei, Aiwen .
CHEMICAL COMMUNICATIONS, 2014, 50 (27) :3623-3626
[39]   A visible light mediated, metal and oxidant free highly efficient cross dehydrogenative coupling (CDC) reaction between quinoxalin-2(1H)-ones and ethers [J].
Mane, Kishor D. ;
Kamble, Rohit B. ;
Suryavanshi, Gurunath .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (19) :7403-7408
[40]   (Diacetoxy)iodobenzene-Mediated Oxidative C-H Amination of Imidazopyridines at Ambient Temperature [J].
Mondal, Susmita ;
Samanta, Sadhanendu ;
Jana, Sourav ;
Hajra, Alakananda .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08) :4504-4510