A Metal-Free Oxidative Amination of Benzoxazoles with Primary Amines and Ammonia

被引:41
作者
Kloeckner, Ulrich [1 ]
Weckenmann, Nicole M. [1 ]
Nachtsheim, Boris J. [1 ]
机构
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
关键词
green chemistry; amination; homogeneous catalysis; iodine; oxidation; C-H BONDS; CATALYZED DIRECT AMINATION; ACTIVATION REACTIONS; FUNCTIONALIZATION; AMIDATION; AZOLES; BENZIMIDAZOLES; TEMPERATURE; FORMAMIDES; SP(2);
D O I
10.1055/s-0031-1289902
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of 2-aminobenzoxazoles is described by a direct oxidative amination of unfunctionalized benzoxazoles with primary amines. The reaction could be performed in the absence of transition metals by using catalytic amounts of a quaternary ammonium iodide and tert-butylhydroperoxide as a cheap and easy-to-handle co-oxidant. In addition to primary amines, aqueous solutions of NH3 were used to introduce a primary amine group into the heterocyclic core.
引用
收藏
页码:97 / 100
页数:4
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共 35 条
  • [1] Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles
    Armstrong, Alan
    Collins, James C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) : 2282 - 2285
  • [2] Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C-H Amination
    Bonnamour, Julien
    Bolm, Carsten
    [J]. ORGANIC LETTERS, 2011, 13 (08) : 2012 - 2014
  • [3] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [4] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction
    Chen, Long
    Shi, Erbo
    Liu, Zhaojun
    Chen, Shulin
    Wei, Wei
    Li, Hong
    Xu, Kai
    Wan, Xiaobing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4085 - 4089
  • [5] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
  • [6] Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines
    Cho, Seung Hwan
    Kim, Ji Young
    Lee, S. Yunmi
    Chang, Sukbok
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) : 9127 - 9130
  • [7] Catalytic C-H amination: recent progress and future directions
    Collet, Florence
    Dodd, Robert H.
    Dauban, Philippe
    [J]. CHEMICAL COMMUNICATIONS, 2009, (34) : 5061 - 5074
  • [8] Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds
    Dick, AR
    Sanford, MS
    [J]. TETRAHEDRON, 2006, 62 (11) : 2439 - 2463
  • [9] A Metal-Free Amination of Benzoxazoles - The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes
    Froehr, Tanja
    Sindlinger, Christian P.
    Kloeckner, Ulrich
    Finkbeiner, Peter
    Nachtsheim, Boris J.
    [J]. ORGANIC LETTERS, 2011, 13 (14) : 3754 - 3757
  • [10] Copper-Catalyzed Oxidative Amination of Benzoxazoles via C-H and C-N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources
    Guo, Shengmei
    Chan, Bo
    Xie, Yinjun
    Xia, Chungu
    Huang, Hanmin
    [J]. ORGANIC LETTERS, 2011, 13 (03) : 522 - 525