FeCl3-catalyzed alkylation of indoles with 1,3-dicarbonyl compounds:: an expedient synthesis of 3-substituted indoles

被引：33
|
作者：
Yadav, J. S. [1 ]
Reddy, B. V. Subba [1 ]
Praneeth, K. [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 01期
关键词：
indoles; iron(III) reagents; 1,3-diketones; C-3; alkylation;
D O I：
10.1016/j.tetlet.2007.09.166
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Indoles undergo smooth alkylation at the 3-position with 1,3-dicarbonyl compounds in the presence of 20 mol % of FeCl3 under mild reaction conditions to produce a wide range of 3-substituted indoles in excellent yields and with high E-selectivity. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：199 / 202
页数：4
相关论文
共 50 条
  • [1] First example of FeCl3-catalyzed alkylation of indoles with pinenes
    Yadav, J. S.
    Reddy, B. V. Subba
    Narasimhulu, G.
    Reddy, N. Sivasankar
    Reddy, P. Narayana
    Purnima, K. V.
    Naresh, P.
    Jagadeesh, B.
    TETRAHEDRON LETTERS, 2010, 51 (02) : 244 - 247
  • [2] Sc(OTf)3-catalyzed alkylation of indoles with propargyl alcohols:: an expeditious synthesis of 3-substituted indoles
    Yadav, J. S.
    Reddy, B. V. Subba
    Rao, K. V. Raghavendra
    Kumar, G. G. K. S. Narayana
    TETRAHEDRON LETTERS, 2007, 48 (31) : 5573 - 5576
  • [3] FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins
    Dal Zotto, Christophe
    Michaux, Julien
    Zarate-Ruiz, Araceli
    Gayon, Eric
    Virieux, David
    Campagne, Jean-Marc
    Terrasson, Vincent
    Pieters, Gregory
    Gaucher, Anne
    Prim, Damien
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 296 - 304
  • [4] An FeCl3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols
    Jana, Umasish
    Maiti, Sukhendu
    Biswas, Srijit
    TETRAHEDRON LETTERS, 2007, 48 (40) : 7160 - 7163
  • [5] Electrochemical [3+2] Cycloaddition of Anilines and 1,3-Dicarbonyl Compounds: Construction of Multisubstituted Indoles
    Chang, Xiaoqiang
    Chen, Xingyu
    Lu, Sixian
    Zhao, Yifan
    Ma, Yue
    Zhang, Dong
    Yang, Lan
    Sun, Peng
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (16) : 2865 - 2871
  • [6] A New Method for the Synthesis of 3-Substituted Indoles
    Natarajan, Rakesh
    Rappai, John P.
    Unnikrishnan, Peruparampil A.
    Radhamani, Sandhya
    Prathapan, Sreedharan
    SYNLETT, 2015, 26 (17) : 2467 - 2471
  • [7] Gold-catalysed direct couplings of indoles and pyrroles with 1,3-dicarbonyl compounds
    Arcadi, A
    Alfonsi, M
    Bianchi, G
    D'Anniballe, G
    Marinelli, F
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) : 331 - 338
  • [8] Interaction of 3-substituted indoles with phenylglyoxal
    Ivonin S.P.
    Lapandin A.V.
    Chemistry of Heterocyclic Compounds, 2005, 41 (11) : 1390 - 1393
  • [9] Synthesis of 3-substituted indoles via reactive alkylideneindolenine intermediates
    Palmieri, Alessandro
    Petrini, Marino
    Shaikh, Rafik R.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (06) : 1259 - 1270
  • [10] New synthesis of 3-substituted indoles using lithium trimethylsilyldiazomethane
    Miyagi, T
    Hari, Y
    Aoyama, T
    TETRAHEDRON LETTERS, 2004, 45 (33) : 6303 - 6305
12345