Copper-Catalyzed [3+2] Annulation of O-Acyl Oximes with p-Hydroquinones for the Synthesis of 5-Hydroxyindoles

被引：0
|
作者：
Zhang, Hui-Peng [1 ]
Chen, Wei [2 ]
Hu, Zi-Jun [1 ]
Lyu, Xinyu [1 ]
Qiao, En-Jun [1 ]
Jin, Wan-Bo [1 ]
Xu, Wen-Ya [1 ]
Ding, Xian-Heng [1 ]
Miao, Chun-Bao [1 ]
Yang, Hai-Tao [1 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Jiangsu, Peoples R China
[2] Changzhou Siyao Pharmaceut Co Ltd, Changzhou 213018, Jiangsu, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期
关键词：
QUINONES; ACETATES;
D O I：
10.1021/acs.joc.4c01722
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed [3 + 2] annulation of O-acyl oximes with 2-electron-withdrawing group substituted p-hydroquinones for the efficient synthesis of polysubstituted 5-hydroxyindoles is developed. Further intramolecular cyclization leads to the concise and rapid construction of several kinds of 3,4- and 4,5-fused polycyclic indoles.
引用
收藏
页码：14968 / 14980
页数：13
相关论文
共 50 条
  • [41] Chiral ferrocenyl P,S-ligands for highly efficient copper-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
    Han, Fu-Zhong
    Yu, Sai-Bo
    Zhang, Cheng
    Hu, Xiang -Ping
    TETRAHEDRON, 2016, 72 (21) : 2616 - 2622
  • [42] Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Propargylic Acetates with Hydrazines: Enantioselective Synthesis of Optically Active 2-Pyrazolines
    Zhang, De-Yang
    Shao, Long
    Xu, Jie
    Hu, Xiang-Ping
    ACS CATALYSIS, 2015, 5 (09): : 5026 - 5030
  • [43] Synthesis of Di- and Trivalent Carbohydrate Mimetics with Oxepane Substructure by Employing Copper-Catalyzed [3+2] Cycloadditions of Alkynes with Azidooxepanes
    Bouche, Lea
    Reissig, Hans-Ulrich
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3697 - 3703
  • [44] Copper(I)-Catalyzed Intramolecular N-N Coupling of Cyclopropyl O-Acyl Ketoximes: Synthesis of Spiro-fused Pyrazolin-5-ones
    Zhang, Zhiguo
    Li, Junlong
    Huang, Guoqing
    Sun, Kai
    Zhang, Guisheng
    Ma, Nana
    Liu, Qingfeng
    Liu, Tongxin
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (12) : 1309 - 1320
  • [45] High-yielding microwave-assisted synthesis of triazole-linked glycodendrimers by copper-catalyzed [3+2] cycloaddition
    Joosten, JAF
    Tholen, NTH
    El Maate, FA
    Brouwer, AJ
    van Esse, GW
    Rijkers, DTS
    Liskamp, RMJ
    Pieters, RJ
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) : 3182 - 3185
  • [46] Copper(II)-Mediated Intermolecular Radical [3+2]-Annulation of N,N-Dimethyl Enaminones: Direct Access to 5-Acyl-3-Furancarboxaldehydes
    Zhang, Biao
    Zhou, Pan
    Xu, Hui
    Huang, Jiuzhong
    Sun, Yulin
    Liu, Donghan
    Yu, Fuchao
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (18) : 4354 - 4359
  • [47] Enantioselective Synthesis of Highly Functionalized Dihydrofurans through Copper-Catalyzed Asymmetric Formal [3+2] Cycloaddition of β-Ketoesters with Propargylic Esters
    Zhu, Fu-Lin
    Wang, Ya-Hui
    Zhang, De-Yang
    Xu, Jie
    Hu, Xiang-Ping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10223 - 10227
  • [48] Copper-catalyzed 2,3-dihydro-1,2,4-triazoles synthesis through [3+2]-cycloaddition of nitrile ylides with azodicarboxylates
    Cai, Bao-Gui
    Li, Qian
    Xuan, Jun
    GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (03): : 191 - 194
  • [49] Tridentate P,N,N-ligand promoted copper-catalyzed [3+2] cycloaddition of propargylic esters with β-enamino esters: synthesis of highly functionalized pyrroles
    Li, Qing
    Hou, Chuan-Jin
    Hui, Yun-Ze
    Liu, Yan-Jun
    Yang, Rui-Feng
    Hu, Xiang-Ping
    RSC ADVANCES, 2015, 5 (104): : 85879 - 85883
  • [50] A rapid efficient microwave-assisted synthesis of a 3′,5′-pentathymidine by copper(I)-catalyzed [3+2] cycloaddition
    Lucas, Romain
    Zerrouki, Rachida
    Granet, Robert
    Krausz, Pierre
    Champavier, Yves
    TETRAHEDRON, 2008, 64 (23) : 5467 - 5471
12345