A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

被引:66
作者
Audisio, Davide [1 ]
Messaoudi, Samir [1 ]
Peyrat, Jean-Francois [1 ]
Brion, Jean-Daniel [1 ]
Alami, Mouad [1 ]
机构
[1] Univ Paris Sud, Fac Pharm, Lab Chim Therapeut, CNRS,BioCIS UMR 8076, F-92296 Chatenay Malabry, France
关键词
palladium; C-N bond coupling reaction; 3-Bromocoumarins; 3-(N-substituted) aminocoumarins;
D O I
10.1016/j.tetlet.2007.07.166
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)(2)/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides. carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6928 / 6932
页数:5
相关论文
共 30 条
  • [11] NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE
    KRANENBURG, M
    VANDERBURGT, YEM
    KAMER, PCJ
    VANLEEUWEN, PWNM
    GOUBITZ, K
    FRAANJE, J
    [J]. ORGANOMETALLICS, 1995, 14 (06) : 3081 - 3089
  • [12] Hydrolysis-free synthesis of 3-aminocoumarins
    Kudale, Amit A.
    Kendall, Jamie
    Warford, C. Chad
    Wilkins, Natasha D.
    Bodwell, Graham J.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (29) : 5077 - 5080
  • [13] Lee HW, 2005, HETEROCYCLES, V65, P1843
  • [14] Synthesis and anti-angiogenesis activity of coumarin derivatives
    Lee, Seokjoon
    Sivakumar, Krishnamoorthy
    Shin, Woon-Seob
    Xie, Fang
    Wang, Qian
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (17) : 4596 - 4599
  • [15] Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
  • [16] 2-U
  • [17] Novobiocin and related coumarins and depletion of heat shock protein 90-dependent signaling proteins
    Marcu, MG
    Schulte, TW
    Neckers, L
    [J]. JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 2000, 92 (03): : 242 - 248
  • [18] The heat shock protein 90 antagonist novobiocin interacts with a previously unrecognized ATP-binding domain in the carboxyl terminus of the chaperone
    Marcu, MG
    Chadli, A
    Bouhouche, I
    Catelli, M
    Neckers, LM
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (47) : 37181 - 37186
  • [19] STRUCTURE-ACTIVITY-RELATIONSHIPS OF POLYMETHOXYFLAVONES AND OTHER FLAVONOIDS AS INHIBITORS OF NONENZYMATIC LIPID-PEROXIDATION
    MORA, A
    PAYA, M
    RIOS, JL
    ALCARAZ, MJ
    [J]. BIOCHEMICAL PHARMACOLOGY, 1990, 40 (04) : 793 - 797
  • [20] Practical palladium catalysts for C-N and C-O bond formation
    Muci, AR
    Buchwald, SL
    [J]. CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 : 131 - 209