Graphene oxide: An efficient recyclable solid acid for the synthesis of bis(indolyl)methanes from aldehydes and indoles in water

被引:52
作者
Wang, Yihong [1 ,2 ]
Sang, Rui [1 ,2 ]
Zheng, Yang [1 ,2 ]
Guo, Li [1 ,2 ]
Guan, Mei [3 ]
Wu, Yong [1 ,2 ]
机构
[1] Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Chengdu 610041, Peoples R China
[3] Sichuan Univ, West China Hosp, 37 GuoXue Rd, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
Graphene oxide; Bis(indolyl)methanes; Friedel-crafts reaction; Recyclable; Water; SOLVENT-FREE CONDITIONS; CATALYZED-REACTIONS; ORGANIC-SOLVENTS; FACILE SYNTHESIS; DERIVATIVES; DISPERSION; BISINDOLE; AGENTS;
D O I
10.1016/j.catcom.2016.09.027
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient synthesis of bis(indolyl)methanes from aldehydes with indoles through graphene oxide-catalyzed Friedel-Crafts alkylation is developed. The reaction proceeds in water by using graphene oxide as the single catalyst to provide the desired products in good to excellent yields. Also, this methodology has a broad substrate scope, and is environment friendly and cost economic. (C) 2016 Published by Elsevier B.V.
引用
收藏
页码:138 / 142
页数:5
相关论文
共 33 条
  • [1] Ammonium chloride catalyzed one-pot diindolylmethanes under solvent-free synthesis of conditions
    Azizian, Javad
    Teimouri, Fatemeh
    Mohammadizadeh, Mohammad Reza
    [J]. CATALYSIS COMMUNICATIONS, 2007, 8 (07) : 1117 - 1121
  • [2] A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases.
    Babu, G
    Sridhar, N
    Perumal, PT
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (09) : 1609 - 1614
  • [3] Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones
    Chen, DP
    Yu, LB
    Wang, PG
    [J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4467 - 4470
  • [4] Choudhary S, 2012, J MATER CHEM, V22, P21032, DOI [10.1039/c2jm34741, 10.1039/c2jm34741e]
  • [5] 6-BROMOTRYPTAMINE DERIVATIVES FROM THE GULF OF CALIFORNIA TUNICATE DIDEMNUM-CANDIDUM
    FAHY, E
    POTTS, BCM
    FAULKNER, DJ
    SMITH, K
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02): : 564 - 569
  • [6] Indolyl carboxylic acids by condensation of indoles with α-keto acids
    Garbe, TR
    Kobayashi, M
    Shimizu, N
    Takesue, N
    Ozawa, M
    Yukawa, H
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05): : 596 - 598
  • [7] Novel approach to bis(indolyl)methanes: De novo synthesis of 1-hydroxyiminomethyl derivatives with anti-cancer properties
    Grosso, Carla
    Cardoso, Ana Lucia
    Lemos, Americo
    Varela, Joao
    Rodrigues, Maria Joao
    Custodio, Luisa
    Barreira, Luisa
    Pinho e Melo, Teresa M. V. D.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 93 : 9 - 15
  • [8] Convenient synthesis of bis(indolyl)alkanes by dithiocarbohydrazone Schiff base/Zn(ClO4)2•6H2O catalyzed Friedel-Crafts reaction of indoles with imines
    Hui, Yong-Hai
    Chen, Yong-Cheng
    Gong, Hai-Wei
    Xie, Zheng-Feng
    [J]. CHINESE CHEMICAL LETTERS, 2014, 25 (01) : 163 - 165
  • [9] PREPARATION OF GRAPHITIC OXIDE
    HUMMERS, WS
    OFFEMAN, RE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (06) : 1339 - 1339
  • [10] Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions
    Ji, SJ
    Wang, SY
    Zhang, Y
    Loh, TP
    [J]. TETRAHEDRON, 2004, 60 (09) : 2051 - 2055