Silver-Catalyzed Radical Tandem Cyclization for the Synthesis of 3,4-Disubstituted Dihydroquinolin-2(1H)-ones

被引:116
作者
Mai, Wen-Peng [1 ]
Wang, Ji-Tao [1 ]
Yang, Liang-Ru [1 ]
Yuan, Jin-Wei [1 ]
Xiao, Yong-Mei [1 ]
Mao, Pu [1 ]
Qu, Ling-Bo [1 ]
机构
[1] Henan Univ Technol, Chem & Chem Engn Sch, Zhengzhou 450001, Henan, Peoples R China
关键词
PLATELET AGGREGATION INHIBITORS; ALIPHATIC CARBOXYLIC-ACIDS; METAL-FREE SYNTHESIS; ACTIVATED ALKENES; 2-OXOQUINOLINE DERIVATIVES; OXIDATIVE TRIFLUOROMETHYLATION; H FUNCTIONALIZATION; OXINDOLE SYNTHESIS; ALPHA-ARYLATION; BOND;
D O I
10.1021/ol403196h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A silver-catalyzed tandem decarboxylative radical addition/cyclization of N-arylcinnamamides with aliphatic carboxylic acids is reported. This method affords a novel and straightforward route to various 3,4-disubstituted dihydroquinolin-2(1H)-ones in aqueous solution.
引用
收藏
页码:204 / 207
页数:4
相关论文
共 69 条
[51]   Palladium-Catalyzed Amidation by Chemoselective C(sp3)?H Activation: Concise Route to Oxindoles Using a Carbamoyl Chloride Precursor [J].
Tsukano, Chihiro ;
Okuno, Masataka ;
Takemoto, Yoshiji .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (11) :2763-2766
[52]   Novel Approach to 3,4-Dihydro-2(1H)-quinolinone Derivatives via Cyclopropane Ring Expansion [J].
Tsuritani, Takayuki ;
Yamamoto, Yuhei ;
Kawasaki, Masashi ;
Mase, Toshiaki .
ORGANIC LETTERS, 2009, 11 (05) :1043-1045
[53]   Silver-Catalyzed Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids in Aqueous Media [J].
Wang, Hua ;
Guo, Li-Na ;
Duan, Xin-Hua .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) :2222-2226
[54]   Silver-catalyzed oxidative coupling/cyclization of acrylamides with 1,3-dicarbonyl compounds [J].
Wang, Hua ;
Guo, Li-Na ;
Duan, Xin-Hua .
CHEMICAL COMMUNICATIONS, 2013, 49 (88) :10370-10372
[55]   Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles [J].
Wei, Hai-Long ;
Piou, Tiffany ;
Dufour, Jeremy ;
Neuville, Luc ;
Zhu, Jieping .
ORGANIC LETTERS, 2011, 13 (09) :2244-2247
[56]   Synthesis of Oxindoles by Iron-Catalyzed Oxidative 1,2-Alkylarylation of Activated Alkenes with an Aryl C(sp2)H Bond and a C(sp3)H Bond Adjacent to a Heteroatom [J].
Wei, Wen-Ting ;
Zhou, Ming-Bo ;
Fan, Jian-Hong ;
Liu, Wei ;
Song, Ren-Jie ;
Liu, Yu ;
Hu, Ming ;
Xie, Peng ;
Li, Jin-Heng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (13) :3638-3641
[57]   Silver-Catalyzed Carboazidation of Arylacrylamides [J].
Wei, Xiao-Hong ;
Li, Ya-Min ;
Zhou, An-Xi ;
Yang, Ting-Ting ;
Yang, Shang-Dong .
ORGANIC LETTERS, 2013, 15 (16) :4158-4161
[58]   Palladium-Catalyzed Oxidative Arylalkylation of Activated Alkenes: Dual C?H Bond Cleavage of an Arene and Acetonitrile [J].
Wu, Tao ;
Mu, Xin ;
Liu, Guosheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (52) :12578-12581
[59]   A room temperature decarboxylation/C-H functionalization cascade by visible-light photoredox catalysis [J].
Xie, Jin ;
Xu, Pan ;
Li, Huamin ;
Xue, Qicai ;
Jin, Hongming ;
Cheng, Yixiang ;
Zhu, Chengjian .
CHEMICAL COMMUNICATIONS, 2013, 49 (50) :5672-5674
[60]   Visible-Light-Induced Trifluoromethylation of N-Aryl Acrylamides: A Convenient and Effective Method To Synthesize CF3-Containing Oxindoles Bearing a Quaternary Carbon Center [J].
Xu, Pan ;
Xie, Jin ;
Xue, Qicai ;
Pan, Changduo ;
Cheng, Yixiang ;
Zhu, Chengjian .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (42) :14039-14042