Copper(II) Oxide Catalyzed Ligand-Free Coupling Reaction of Heteroarenes with Bromoalkynes

被引:18
作者
Das, Biswanath [1 ]
Reddy, Gandolla Chinna [1 ]
Balasubramanyam, Penagaluri [1 ]
Salvanna, N. [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500607, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2011年 / 05期
关键词
coupling reaction; ligand-free conditions; copper(II) oxide; N-alkynylheteroarene; N-(2-bromovinyl)heteroarene; ALPHA-AMINO PHOSPHONATES; IMIDAZOLES; YNAMIDES; YNAMINES; SALTS;
D O I
10.1055/s-0030-1258403
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The coupling reaction of imidazoles and pyrazoles with bromoacetylenes has efficiently been carried out under ligand-free conditions in the presence of copper(II) oxide as the catalyst using potassium hydroxide in 1,4-dioxane at 80 degrees C. The method is a simpler access to N-alk-1-ynyl- and/or N-(2-bromovinyl)-substituted heteroarenes.
引用
收藏
页码:816 / 820
页数:5
相关论文
共 16 条
  • [1] Photoexcitations in carbazolyl substituted polydiacetylene (PDA) fullerene composites
    Brabec, C
    Scharber, M
    Johansson, H
    Comoretto, D
    Dellepiane, G
    Moggio, I
    Cravino, A
    Hummelen, JC
    Sariciftci, NS
    [J]. SYNTHETIC METALS, 1999, 101 (1-3) : 298 - 299
  • [2] AN IMPROVED PROCEDURE FOR N-ETHYNYLPYRROLE
    BRANDSMA, L
    MALKINA, AG
    TROFIMOV, BA
    [J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (19) : 2721 - 2724
  • [3] Cu-Catalyzed N-Alkynylation of Imidazoles, Benzimidazoles, Indazoles, and Pyrazoles Using PEG as Solvent Medium
    Burley, Glenn A.
    Davies, David L.
    Griffith, Gerry A.
    Lee, Michael
    Singh, Kuldip
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) : 980 - 983
  • [4] A Simple, Advantageous Synthesis of 5-Substituted 1H-Tetrazoles
    Das, Biswanath
    Reddy, Cheruku Ravindra
    Kumar, Duddukuri Nandan
    Krishnaiah, Martha
    Narender, Ravirala
    [J]. SYNLETT, 2010, (03) : 391 - 394
  • [5] Organic Reactions in Water: A Distinct Novel Approach for an Efficient Synthesis of α-Amino Phosphonates Starting Directly from Nitro Compounds
    Das, Biswanath
    Satyalakshmi, Gandham
    Suneel, Kanaparthy
    Damodar, Kongara
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) : 8400 - 8402
  • [6] A Simple and Efficient Access to α-Amino Phosphonates from N-Benzyloxycarbonylamino Sulfones Using Indium(III) Chloride
    Das, Biswanath
    Damodar, Kongara
    Bhunia, Nisith
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5607 - 5609
  • [7] Preparation of trifluoromethylated ynamines and their reactions with some electrophilic reagents
    Ishihara, T
    Mantani, T
    Konno, T
    Yamanaka, H
    [J]. TETRAHEDRON, 2006, 62 (16) : 3783 - 3793
  • [8] SYNTHESIS, TRANSFORMATIONS AND BIOLOGICAL-ACTIVITY OF CHLORO ENAMINES AND YNAMINES DERIVED FROM CHLOROALKENYL-N-SUBSTITUTED AND ALKYNYL-N-SUBSTITUTED PURINE AND PYRIMIDINE-BASES OF NUCLEIC-ACIDS
    JOSHI, RV
    XU, ZQ
    KSEBATI, MB
    KESSEL, D
    CORBETT, TH
    DRACH, JC
    ZEMLICKA, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08): : 1089 - 1098
  • [9] Katritzky AR, 2004, HETEROCYCLES, V63, P1455
  • [10] A convenient synthesis of new 1-alkynyl-1H-benzotriazoles by reaction of alkynyl(phenyl)iodonium salts with benzotriazole ion
    Kitamura, T
    Tashi, N
    Tsuda, K
    Chen, HY
    Fujiwara, Y
    [J]. HETEROCYCLES, 2000, 52 (01) : 303 - 312