Palladium-Catalyzed Primary Amine-Directed Decarboxylative Annulation of α-Oxocarboxylic Acids: Access to Indolo[1,2-a]quinazolines

被引:35
作者
Jiang, Guangbin [1 ]
Wang, Shoucai [1 ]
Zhang, Jun [1 ]
Yu, Jianwen [1 ]
Zhang, Ziang [1 ]
Ji, Fanghua [1 ]
机构
[1] Guilin Univ Technol, Coll Chem & Bioengn, Guangxi Key Lab Electrochem & Magnetochem Funct M, Guilin 541004, Peoples R China
关键词
palladium-catalyzed; alpha-oxocarboxylic acids; decarboxylative annulation; directing group; NITROGEN-CONTAINING HETEROCYCLES; O-METHYL KETOXIMES; C-H; ORTHO-ACYLATION; CARBOXYLIC-ACIDS; EFFICIENT SYNTHESIS; N-NITROSOANILINES; ARENES; AZOBENZENES; CYCLIZATION;
D O I
10.1002/adsc.201900001
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient protocol for the preparation of indolo[1,2-a]quinazolines via palladium-catalyzed decarboxylative annulation of indols with alpha-oxocarboxylic acids has been realized by using primary amine as a directing group (DG). This transformation proceeds smoothly with exclusive regioselectivity and represents an one-pot Domino synthesis of indo-lo[1,2-a]quinazolines from alpha-oxocarboxylic acids.
引用
收藏
页码:1798 / 1802
页数:5
相关论文
共 62 条
[1]  
[Anonymous], 2011, ANGEW CHEM INT EDIT
[2]   Palladium-Catalyzed Decarboxylative ortho-Acylation of O-Methyl Ketoximes via Direct sp2 C-H Bond Activation [J].
Cai Haiting ;
Li Dandan ;
Liu Zi ;
Wang Guanwu .
ACTA CHIMICA SINICA, 2013, 71 (05) :717-721
[3]   Cu-Catalyzed Radical Cascade Annulations of Alkyne-Tethered N-Alkoxyamides with Air: Facile Access to Isoxazolidine/1,2-Oxazinane-Fused Isoquinolin-1(2H)-ones [J].
Chen, Fei ;
Lai, Sheng-Qiang ;
Zhu, Fei-Fei ;
Meng, Qiang ;
Jiang, Yu ;
Yu, Wei ;
Han, Bing .
ACS CATALYSIS, 2018, 8 (09) :8925-8931
[4]   Decarbonylative Coupling of α-Keto Acids and Ynamides for Synthesis of β-Keto Imides [J].
Chen, Renjie ;
Zeng, Linwei ;
Huang, Bo ;
Shen, Yangyong ;
Cui, Sunliang .
ORGANIC LETTERS, 2018, 20 (11) :3377-3380
[5]   C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation [J].
Chen, Xiaopei ;
Cui, Xiuling ;
Wu, Yangjie .
ORGANIC LETTERS, 2016, 18 (15) :3722-3725
[6]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[7]   A new approach to arylhydrazides via the reaction of the Mitsunobu reagent with arynes: further application to access diverse nitrogen-containing heterocycles in one pot [J].
Cheng, Bin ;
Bao, Bian ;
Chen, Yanhe ;
Wang, Ning ;
Li, Yun ;
Wang, Renqi ;
Zhai, Hongbin .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08) :1636-1639
[8]   Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis [J].
Cheng, Wan-Min ;
Shang, Rui ;
Yu, Hai-Zhu ;
Fu, Yao .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (38) :13191-13195
[9]   Radical-mediated direct C-H amination of arenes with secondary amines [J].
Cosgrove, Sebastian C. ;
Plane, John M. C. ;
Marsden, Stephen P. .
CHEMICAL SCIENCE, 2018, 9 (32) :6647-6652
[10]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238