General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem

被引:390
作者
Chernyak, Natalia [1 ]
Gevorgyan, Vladimir [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
关键词
cyclization; heterocycles; homogeneous catalysis; imidazopyridines; multicomponent reactions; PERIPHERAL BENZODIAZEPINE-RECEPTOR; MULTICOMPONENT SYNTHESIS; ALDEHYDES; ALKYNES; PROPARGYLAMINES; AFFINITY; LIGANDS; BINDING; AMINES;
D O I
10.1002/anie.200907291
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Three is not a crowd: A method for the construction of Imidazopyridine, imidazoquinoline, and imidazoisoquinoline frameworks has been developed. The synthetic utility of this method was demonstrated in a highly efficient one-pot synthesis of the drugs alpidem and Zolpidem (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2743 / 2746
页数:4
相关论文
共 38 条
  • [1] SYNTHESIS OF [C-14] ZOLPIDEM
    ALLEN, J
    TIZOT, A
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1986, 23 (04) : 393 - 400
  • [2] ALLEN J, 1986, LABELLED COMPD RADIO, V23, P807
  • [3] [Anonymous], 2006, Angew. Chem, DOI DOI 10.1002/ANGE.200602917
  • [4] Synthesis of 2-benzylimidazo[2,1-b][1,3]benzothiazoles through palladium-catalyzed heteroannulation of acetylenic compounds
    Bakherad, Mohammad
    Nasr-Isfahani, Hossein
    Keivanloo, Ali
    Sang, Golnaz
    [J]. TETRAHEDRON LETTERS, 2008, 49 (43) : 6188 - 6191
  • [5] Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 2-benzylimidazo[1,2-a]pyridine
    Bakherad, Mohammad
    Nasr-Isfahani, Hossein
    Keivanloo, Ali
    Doostmohammadi, Nesa
    [J]. TETRAHEDRON LETTERS, 2008, 49 (23) : 3819 - 3822
  • [6] Enantioselective one-pot three-component synthesis of propargylamines
    Bisai, Alakesh
    Singh, Vinod K.
    [J]. ORGANIC LETTERS, 2006, 8 (11) : 2405 - 2408
  • [7] Couty F., 2008, COMPREHENSIVE HETERO, V11, P409
  • [8] 2-Phenyl-imidazo[1,2-a]pyridine Compounds Containing Hydrophilic Groups as Potent and Selective Ligands for Peripheral Benzodiazepine Receptors: Synthesis, Binding Affinity and Electrophysiological Studies
    Denora, Nunzio
    Laquintana, Valentino
    Pisu, Maria Giuseppina
    Dore, Riccardo
    Murru, Luca
    Latrofa, Andrea
    Trapani, Giuseppe
    Sanna, Enrico
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (21) : 6876 - 6888
  • [9] Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot
    DiMauro, Erin F.
    Kennedy, Joseph M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) : 1013 - 1016
  • [10] Synthesis and biological evaluation of substituted [18F]imidazo[1,2-a]pyridines and [18F]pyrazolo[1,5-a]pyrimidines for the study of the peripheral benzodiazepine receptor using positron emission tomography
    Fookes, Christopher J. R.
    Pham, Tien Q.
    Mattner, Filomena
    Greguric, Ivan
    Loc'h, Christian
    Liu, Xiang
    Berghofer, Paula
    Shepherd, Rachael
    Gregoire, Marie-Claude
    Katsifis, Andrew
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (13) : 3700 - 3712