HOAc catalyzed three-component reaction for the synthesis of 3,3′-(arylmethylene)bis(1H-indoles)

被引：2
作者：
Li, Heng [1 ]
Zhu, Yan [1 ]
Jiang, Cong [1 ]
Wei, Jia [1 ]
Liu, Ping [1 ]
Sun, Peipei [1 ]
机构：
[1] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Sch Chem & Mat Sci, Jiangsu Prov Key Lab Mat Cycle Proc & Pollut Cont, Nanjing 210023, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 16期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; INDOLE ALKALOIDS; 3+2 ANNULATION; ARYLATION; FUNCTIONALIZATION; CYCLIZATION; ACTIVATION; DISCOVERY; ALDEHYDES; PROGRESS;
D O I：
10.1039/d2ob00395c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient HOAc catalyzed three-component reaction of 2-(arylethynyl)anilines with arylaldehydes has been achieved, which leads to the generation of 3,3 '-(arylmethylene)bis(1H-indoles) with good to excellent yields and high regioselectivity under transition-metal-free conditions. Four new C-C and C-N bonds were effectively formed in a one-pot procedure. Subsequent research on the reaction mechanism indicated that the reaction likely involved the processes of intramolecular cyclization and cascade intermolecular dehydration condensation.
引用
收藏
页码：3365 / 3374
页数：10
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共 67 条
  • [1] Catalytic Functionalization of Indoles in a New Dimension
    Bandini, Marco
    Eichholzer, Astrid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
  • [2] Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents
    Bharate, Sandip B.
    Bharate, Jaideep B.
    Khan, Shabana I.
    Tekwani, Babu L.
    Jacob, Melissa R.
    Mudududdla, Ramesh
    Yadav, Rammohan R.
    Singh, Baljinder
    Sharma, P. R.
    Maity, Sudip
    Singh, Baldev
    Khan, Ikhlas A.
    Vishwakarma, Ram A.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 : 435 - 443
  • [3] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [4] Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1911 - 1923
  • [5] Indole Synthesis Using Silver Catalysis
    Clarke, Aimee K.
    Ho, Hon E.
    Rossi-Ashton, James A.
    Taylor, Richard J. K.
    Unsworth, William P.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (11) : 1900 - 1911
  • [6] Visible light-mediated chemistry of indoles and related heterocycles
    Festa, Alexey A.
    Voskressensky, Leonid G.
    Van der Eycken, Erik V.
    [J]. CHEMICAL SOCIETY REVIEWS, 2019, 48 (16) : 4401 - 4423
  • [7] Tandem inverse-electron-demand hetero-/retro-Diels-Alder reactions for aromatic nitrogen heterocycle synthesis
    Foster, Radleigh A. A.
    Willis, Michael C.
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (01) : 63 - 76
  • [8] Research Progress of Synthesis of Bis(indolyl)methanes
    Gong, Haiwei
    Xie, Zhengfeng
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (07) : 1195 - 1207
  • [9] HAMACANTHIN-A AND HAMACANTHIN-B, NEW ANTIFUNGAL BIS INDOLE ALKALOIDS FROM THE DEEP-WATER MARINE SPONGE, HAMACANTHA SP
    GUNASEKERA, SP
    MCCARTHY, PJ
    KELLYBORGES, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1994, 57 (10): : 1437 - 1441
  • [10] Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis
    Hong, Feng-Lin
    Ye, Long-Wu
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (09) : 2003 - 2019
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