A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine

被引:160
|
作者
Sharma, GVM [1 ]
Reddy, JJ [1 ]
Lakshmi, PS [1 ]
Krishna, PR [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 3, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
Bis(indolyl)methanes; aldehydes; sugar aldehydes; electrophilic substitution; trichloro-1,3,5-triazine;
D O I
10.1016/j.tetlet.2004.08.084
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient electrophilic substitution reaction of indoles with a variety of aldehydes was carried out using catalytic trichloro-1,3,5-triazine (10mol%,) in acetonitrile to furnish the corresponding bis(indolyl)methanes in excellent yields. Similarly, sugar derived aldehydes gave hitherto unknown bis(indolyl)glycoconjugates in very good yields. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7729 / 7732
页数:4
相关论文
共 50 条
  • [1] A mild and versatile synthesis of bis(indolyl)methanes and tris(indolyl)alkanes catalyzed by antimony trichloride
    Kundu, Pradip
    Maiti, Gourhari
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (09): : 1402 - 1406
  • [2] Zeolite catalyzed synthesis of bis(indolyl) methanes
    Reddy, AV
    Ravinder, K
    Reddy, VLN
    Goud, TV
    Ravikanth, V
    Venkateswarlu, Y
    SYNTHETIC COMMUNICATIONS, 2003, 33 (21) : 3687 - 3694
  • [3] Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane
    Garcia Merinos, J. Pablo
    Loez Ruiz, Heraclio
    Lopez, Yliana
    Rojas Lima, Susana
    LETTERS IN ORGANIC CHEMISTRY, 2015, 12 (05) : 332 - 336
  • [4] Facile Synthesis of Bis(indolyl)methanes Catalyzed by α-Chymotrypsin
    Xie, Zong-Bo
    Sun, Da-Zhao
    Jiang, Guo-Fang
    Le, Zhang-Gao
    MOLECULES, 2014, 19 (12) : 19665 - 19677
  • [5] An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride
    Zhang, ZH
    Yin, L
    Wang, YM
    SYNTHESIS-STUTTGART, 2005, (12): : 1949 - 1954
  • [6] Cyanuric chloride: Trichloro-1,3,5-triazine
    Haval, Kishan P.
    SYNLETT, 2006, (13) : 2156 - 2157
  • [7] A practical synthesis of bis(indolyl)methanes employing boric acid
    Yadav, Jhillu S.
    Gupta, Manoj K.
    Jain, Ruchi
    Yadav, Nagendra N.
    Reddy, Basi V. Subba
    MONATSHEFTE FUR CHEMIE, 2010, 141 (09): : 1001 - 1004
  • [8] A practical synthesis of bis(indolyl)methanes employing boric acid
    Jhillu S. Yadav
    Manoj K. Gupta
    Ruchi Jain
    Nagendra N. Yadav
    Basi V. Subba Reddy
    Monatshefte für Chemie - Chemical Monthly, 2010, 141 : 1001 - 1004
  • [9] CuBr2-catalyzed synthesis of bis(indolyl)methanes
    Mo, LP
    Ma, ZC
    Zhang, ZH
    SYNTHETIC COMMUNICATIONS, 2005, 35 (15) : 1997 - 2004
  • [10] Synthesis of bis(indolyl)methanes catalyzed by surface modified zirconia
    Nadkarni, Sharmin V.
    Gawande, Manoj B.
    Jayaram, Radha V.
    Nagarkar, Jayashree M.
    CATALYSIS COMMUNICATIONS, 2008, 9 (08) : 1728 - 1733