Copper-Catalyzed [4+1+1] Annulation of Ammonium Salts and Anthranils: Synthesis of 2,3-Diaroylquinolines

被引：1
|
作者：
Yang, Jia-Cheng [1 ,2 ]
Ma, Cheng-Wei [1 ,2 ]
Liao, Mao-Lin [1 ,2 ]
Li, Ping-Gui [3 ]
Zou, Liang-Hua [1 ,2 ,4 ]
机构：
[1] Jiangnan Univ, Key Lab Carbohydrate Chem & Biotechnol, Minist Educ, Wuxi 214122, Peoples R China
[2] Jiangnan Univ, Sch Life Sci & Hlth Engn, Wuxi 214122, Peoples R China
[3] Wuxi Univ, Sch Environm Engn, Wuxi 214105, Peoples R China
[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 11期
关键词：
MEDIATED ASYMMETRIC EPOXIDATIONS; C-H; QUINOLINE; YLIDES; MECHANISM; NITROGEN;
D O I：
10.1021/acs.joc.3c02851
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper(I)-catalyzed protocol is developed for the synthesis of various 2,3-diaroylquinolines starting from achiral ammonium salts and anthranils through [4+1+1] annulation. Using copper(I) chloride as the sole catalyst, this reaction is featured with easily available starting materials, broad substrate scope, good yields and simple reaction conditions.
引用
收藏
页码：7446 / 7454
页数：9
相关论文
共 50 条
  • [41] Copper-catalyzed intermolecular generation of ammonium ylides with subsequent [2,3]sigmatropic rearrangement. Efficient synthesis of bifunctional homoallylamines
    Honda, Kiyoshi
    Shibuya, Hiromasa
    Yasui, Hiroto
    Hoshino, Yujiro
    Inoue, Seiichi
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (01) : 142 - 147
  • [42] Copper-catalyzed formal [1+2+2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines
    Dong, Shanliang
    Huang, Jingjing
    Sha, Hongkai
    Qiu, Lihua
    Hu, Wenhao
    Xu, Xinfang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (10) : 1926 - 1932
  • [43] Synthesis of Functionalized Indolizines via Copper-Catalyzed Annulation of 2-Alkylazaarenes with α,β-Unsaturated Carboxylic Acids
    Yang, Yuzhu
    Xie, Chunsong
    Xie, Yongju
    Zhang, Yuhong
    ORGANIC LETTERS, 2012, 14 (04) : 957 - 959
  • [44] A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles
    Xie, Haodong
    Zhao, Wei
    Wei, Heping
    Yu, Yang
    Zhao, Lili
    Baell, Jonathan B.
    Huang, Fei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4546 - 4555
  • [45] Copper-catalyzed annulation of heteroaromatic β-halo-α,β-unsaturated carboxylic acids with alkynes for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones
    Gu, Da-Wei
    Guo, Xun-Xiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (32) : 6114 - 6120
  • [46] Copper-Catalyzed Domino Synthesis of 4-Oxopyrimido[1,2-a]indole Derivatives
    Wang, Yuyuan
    Wang, Ruji
    Jiang, Yuyang
    Tan, Chunyan
    Fu, Hua
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (14-15) : 2928 - 2935
  • [47] Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes
    Song, Jin
    Zhang, Zi-Jing
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (19) : 5212 - 5216
  • [48] Copper-Catalyzed Radical [2+2+1] Annulation of Benzene-Linked 1,n-Enynes with Azide: Fused Pyrroline Compounds
    Ouyang, Xuan-Hui
    Song, Ren-Jie
    Liu, Yu
    Hu, Ming
    Li, Jin-Heng
    ORGANIC LETTERS, 2015, 17 (24) : 6038 - 6041
  • [49] Copper-Catalyzed 2:1 Coupling Reaction of Arynes with Alkynes
    Yoshida, Hiroto
    Morishita, Takami
    Nakata, Hiromi
    Ohshita, Joji
    ORGANIC LETTERS, 2009, 11 (02) : 373 - 376
  • [50] An efficient copper-catalyzed synthesis of hexahydro-1H-phenothiazines
    Prasad, D. J. C.
    Sekar, Govindasamy
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (24) : 5091 - 5097
12345