Direct Synthesis of Dihydrobenzo[a]carbazoles via Palladium-Catalyzed Domino Annulation of Indoles

被引:34
|
作者
Jafarpour, Farnaz [1 ]
Hazrati, Hamideh [1 ]
机构
[1] Univ Tehran, Sch Chem, Univ Coll Sci, Tehran 141556455, Iran
基金
美国国家科学基金会;
关键词
benzo[a]carbazoles; bromoalkylindoles; domino reactions; one-step synthesis; palladium catalyst; ALKYLATION/DIRECT ARYLATION REACTION; NITROGEN-CONTAINING HETEROCYCLES; THROMBOPOIETIN TPO RECEPTOR; SMALL-MOLECULE AGONISTS; DERIVATIVES; COMPLEXES; SEQUENCE; LIGANDS; CYCLOPALLADATION; BINDING;
D O I
10.1002/adsc.200900725
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A straightforward one-step synthesis of annulated indoles via palladium-catalyzed, norbornene-mediated sequential intermolecular aryl ortho-alkylation/intramolecular indole c-h activation has been devised. This method provides ail efficient route to a wide variety of substituted 6,1.1-dihydro-5 H-benzo[a]carbazoles from readily accessible 3-bromoalkylindoles and iodoarenes.
引用
收藏
页码:363 / 367
页数:5
相关论文
共 50 条
  • [41] Palladium-Catalyzed Regioselective Alkoxylation via C-H Bond Activation in the Dihydrobenzo[c]acridine Series
    Large, Benjamin
    Bourdreux, Flavien
    Damond, Aurelie
    Gaucher, Anne
    Prim, Damien
    CATALYSTS, 2018, 8 (04):
  • [42] Palladium-catalyzed domino cyclization/direct functionalization involving the insertion of SO2
    Zhang, Xinwei
    Lu, Yaoyao
    Zhang, Shuoshuo
    Lin, Shuizhen
    Chen, Mengting
    Huang, Xiaolei
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (12) : 5101 - 5106
  • [43] Domino Catalysis: Palladium-Catalyzed Carbonylation of Allylic Alcohols to ,-Unsaturated Esters
    Liu, Qiang
    Wu, Lipeng
    Jiao, Haijun
    Fang, Xianjie
    Jackstell, Ralf
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) : 8064 - 8068
  • [44] Palladium-Catalyzed Carbonylative Synthesis of Benzogerminones
    Chen, Bo
    Wu, Xiao-Feng
    SYNLETT, 2019, 30 (13) : 1592 - 1596
  • [45] Palladium-Catalyzed Synthesis of Arylpropargyl Ethers
    Gowrisankar, Saravanan
    Neumann, Helfried
    Beller, Matthias
    CHEMCATCHEM, 2011, 3 (09) : 1439 - 1441
  • [46] Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles
    Thansandote, Praew
    Hulcoop, David G.
    Langer, Michael
    Lautens, Mark
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) : 1673 - 1678
  • [47] Copper- or Palladium-Catalyzed Amidation and Cyclization Route for the Synthesis of Pyrimido[4,5-b]carbazoles
    Kumar, Arepalli Sateesh
    Nagarajan, Rajagopal
    SYNTHESIS-STUTTGART, 2013, 45 (20): : 2893 - 2903
  • [48] Palladium-catalyzed synthesis of 2,3-disubstituted indoles via arylation of ortho-alkynylanilines with arylsiloxanes
    Hsia, Yang-Ting
    Lu, Yu-Lin
    Bai, Rekha
    Badsara, Satpal Singh
    Lee, Chin-Fa
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (37) : 7602 - 7610
  • [49] Synthesis of 1,2-Disubstituted Acenaphthylenes by Palladium-Catalyzed Annulation Reactions of Dibromoarenes with Internal Alkynes
    An, Wenbo
    Li, Gaoqiang
    Ma, Jun
    Tian, Youping
    Xu, Feng
    SYNLETT, 2014, 25 (11) : 1585 - 1590
  • [50] SYNTHESIS OF PHENANTHRIDINES AND RELATED COMPOUNDS BY PALLADIUM-CATALYZED DIRECT COUPLING VIA C-H AND N-H BOND CLEAVAGES
    Takeda, Daisuke
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    HETEROCYCLES, 2012, 86 (01) : 487 - 496