IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores

被引:295
作者
Barluenga, J [1 ]
Trincado, M [1 ]
Rubio, E [1 ]
González, JM [1 ]
机构
[1] Univ Oviedo, CSIC, Unidad Asociada, Inst Quim Organomet Enrique Moles, E-33071 Oviedo, Spain
关键词
alkynes; cyclization; electrophilic addition; halogenation; nitrogen heterocycles;
D O I
10.1002/anie.200351303
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
All at once! Indoles can be assembled and iodinated in a one-pot process (see scheme) from anilines and their derivatives. This metal-free addition of nitrogen compounds to alkynes is a clean reaction that is promoted by iodonium cations. Such a process provides a general pathway towards utilization of the biologically relevant indole core.
引用
收藏
页码:2406 / 2409
页数:4
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共 72 条
  • [1] Preparation of 6-chloro-5-fluoroindole via the use of palladium and copper-mediated heterocyclisations
    Adams, DR
    Duncton, MAJ
    Roffey, JRA
    Spencer, J
    [J]. TETRAHEDRON LETTERS, 2002, 43 (42) : 7581 - 7583
  • [2] Arcadi A, 2000, SYNLETT, P647
  • [3] BARLUENGA F, 2001, ANGEW CHEM, V113, P3491
  • [4] IODO-CARBOFUNCTIONALIZATION OF ALKYNES WITH AROMATIC RINGS AND IPY2BF4
    BARLUENGA, J
    RODRIGUEZ, MA
    GONZALEZ, JM
    CAMPOS, PJ
    [J]. TETRAHEDRON LETTERS, 1990, 31 (29) : 4207 - 4210
  • [5] BARLUENGA J, 1993, ANGEW CHEM INT EDIT, V32, P893, DOI 10.1002/anie.199308931
  • [6] IODINE-INDUCED STEREOSELECTIVE CARBOCYCLIZATIONS - A NEW METHOD FOR THE SYNTHESIS OF CYCLOHEXANE AND CYCLOHEXENE DERIVATIVES
    BARLUENGA, J
    GONZALEZ, JM
    CAMPOS, PJ
    ASENSIO, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (11): : 1546 - 1547
  • [7] Barluenga J, 2001, ANGEW CHEM INT EDIT, V40, P3389, DOI 10.1002/1521-3773(20010917)40:18<3389::AID-ANIE3389>3.0.CO
  • [8] 2-V
  • [9] Reactions of (tert-butyldimethylsilyl) alkynes with IPy2BF4: Selective synthesis of novel head-to-head dimers
    Barluenga, J
    Llorente, I
    AlvarezGarcia, LJ
    Gonzalez, JM
    Campos, PJ
    Diaz, MR
    GarciaGranda, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (29) : 6933 - 6934
  • [10] Barluenga J, 1998, ANGEW CHEM INT EDIT, V37, P3136, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3136::AID-ANIE3136>3.0.CO