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
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 08期
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
    Cai Haiting
    Li Dandan
    Liu Zi
    Wang Guanwu
    [J]. 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
    Chen, Fei
    Lai, Sheng-Qiang
    Zhu, Fei-Fei
    Meng, Qiang
    Jiang, Yu
    Yu, Wei
    Han, Bing
    [J]. ACS CATALYSIS, 2018, 8 (09): : 8925 - 8931
  • [4] Decarbonylative Coupling of α-Keto Acids and Ynamides for Synthesis of β-Keto Imides
    Chen, Renjie
    Zeng, Linwei
    Huang, Bo
    Shen, Yangyong
    Cui, Sunliang
    [J]. 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
    Chen, Xiaopei
    Cui, Xiuling
    Wu, Yangjie
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3722 - 3725
  • [6] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
    Chen, Zhengkai
    Wang, Binjie
    Zhang, Jitan
    Yu, Wenlong
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. 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
    Cheng, Bin
    Bao, Bian
    Chen, Yanhe
    Wang, Ning
    Li, Yun
    Wang, Renqi
    Zhai, Hongbin
    [J]. 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
    Cheng, Wan-Min
    Shang, Rui
    Yu, Hai-Zhu
    Fu, Yao
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (38) : 13191 - 13195
  • [9] Radical-mediated direct C-H amination of arenes with secondary amines
    Cosgrove, Sebastian C.
    Plane, John M. C.
    Marsden, Stephen P.
    [J]. CHEMICAL SCIENCE, 2018, 9 (32) : 6647 - 6652
  • [10] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
    Deiters, A
    Martin, SF
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
1234567