An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions

被引:57
|
作者
Chen, Yu [1 ]
Markina, Nataliya A. [1 ]
Larock, Richard C. [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
基金
美国国家卫生研究院;
关键词
Microwave-assisted; One-pot; Three-component coupling; Indoles; Sonogashira coupling; PALLADIUM-CATALYZED CYCLIZATION; O-ALKYNYLTRIFLUOROACETANILIDES; ELECTROPHILIC CYCLIZATION; 2,3-DISUBSTITUTED INDOLES; INTERNAL ALKYNES; ARYL; CHEMISTRY; HALIDES; 3-IODOINDOLES; HETEROCYCLES;
D O I
10.1016/j.tet.2009.07.075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A microwave-assisted, one-pot, three-component coupling reaction for the synthesis of indoles has been developed. The reaction is carried out in two steps under standard Sonogashira coupling conditions from an N-substituted/N,N-disubstituted 2-iodoaniline and a terminal alkyne, followed by the addition of acetonitrile and an aryl iodide. A variety of polysubstituted indoles have been prepared in moderate to excellent yields using the present method. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8908 / 8915
页数:8
相关论文
共 50 条
  • [1] Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions
    Markina, Nataliya A.
    Chen, Yu
    Larock, Richard C.
    TETRAHEDRON, 2013, 69 (13) : 2701 - 2713
  • [2] Microwave-assisted one-pot synthesis of 2-substituted indoles
    Chen, Jing
    Hu, Yong-Zhou
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (07) : 996 - 1000
  • [3] Highly efficient, three-component, one-pot, microwave-assisted synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions
    Markina, Nataliya A.
    Chen, Yu
    Larock, Richard C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [4] Microwave-assisted efficient one-pot synthesis of nitriles in dry media
    Yadav, JS
    Reddy, BVS
    Madan, C
    JOURNAL OF CHEMICAL RESEARCH, 2001, (05) : 190 - 191
  • [5] Microwave-assisted one-pot nitrene insertion-decarboxylation synthesis of substituted indoles
    Miner, Elise
    Jones, Graham
    Ranasinghe, Nadeesha
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [6] Microwave-assisted one-pot synthesis of α, β-unsaturated amides under solvent-free conditions
    Jiang, Shilei
    Xie, Yuanyuan
    Yu, Xiaochun
    JOURNAL OF CHEMICAL RESEARCH, 2009, (01) : 24 - 26
  • [7] Microwave-Assisted One-Pot Synthesis of Pyrazolone Derivatives under Solvent-Free Conditions
    Ma, Ruoqun
    Zhu, Jin
    Liu, Jie
    Chen, Lili
    Shen, Xu
    Jiang, Hualiang
    Li, Jian
    MOLECULES, 2010, 15 (05) : 3593 - 3601
  • [8] An efficient Biginelli one-pot synthesis of new naphthalene-condensed oxazine derivatives under microwave-assisted conditions
    Azizian, Javad
    Yadollahzadeh, Khadijeh
    Delbari, Akram Sadat
    Ghanbari, Mohammad Mehdi
    MONATSHEFTE FUR CHEMIE, 2012, 143 (10): : 1417 - 1420
  • [9] An efficient Biginelli one-pot synthesis of new naphthalene-condensed oxazine derivatives under microwave-assisted conditions
    Javad Azizian
    Khadijeh Yadollahzadeh
    Akram Sadat Delbari
    Mohammad Mehdi Ghanbari
    Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 1417 - 1420
  • [10] Efficient Microwave-assisted One-pot Synthesis of Novel Spironaphthopyrano-one Derivatives
    Meshram, G.
    Wagh, P.
    Amratlal, V.
    Deshpande, S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1639 - 1645