Conversion of Pyridine to Imidazo[1,2-a]pyridines by Copper-Catalyzed Aerobic Dehydrogenative Cyclization with Oxime Esters

被引:160
作者
Huang, Huawen [1 ]
Ji, Xiaochen [1 ]
Tang, Xiaodong [1 ]
Zhang, Min [1 ]
Li, Xianwei [1 ]
Jiang, Huanfeng [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金; 国家教育部博士点专项基金资助;
关键词
PYRROLE-CONTAINING HETEROCYCLES; NICKEL/LEWIS ACID CATALYSIS; C-H FUNCTIONALIZATION; EFFICIENT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; SELECTIVE ALKENYLATION; OXIDATIVE SYNTHESIS; BOND ACTIVATION; 2-AMINOPYRIDINES; ACETATES;
D O I
10.1021/ol403105p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid and environmentally friendly conversion of pyridine to imidazo[1,2-a]pyridines has been developed via copper-catalyzed aerobic dehydrogenative cyclization with ketone oxime esters.
引用
收藏
页码:6254 / 6257
页数:4
相关论文
共 50 条
  • [1] Synthesis and cytotoxic activity of 2-methylimidazo[1,2-a]pyridine- and quinoline-substituted 2-aminopyrimidine derivatives
    Angel Vilchis-Reyes, Miguel
    Zentella, Alejandro
    Angel Martinez-Urbina, Miguel
    Guzman, Angel
    Vargas, Omar
    Ramirez Apan, Maria Teresa
    Ventura Gallegos, Jose Luis
    Diaz, Eduardo
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) : 379 - 386
  • [2] A Novel Solvent-Free Approach to Imidazole Containing Nitrogen-Bridgehead Heterocycles
    Attanasi, Orazio A.
    Bianchi, Luca
    Campisi, Linda A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Mantellini, Fabio
    [J]. ORGANIC LETTERS, 2013, 15 (14) : 3646 - 3649
  • [3] Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale
    Bagdi, Avik Kumar
    Rahman, Matiur
    Santra, Sougata
    Majee, Adinath
    Hajra, Alakananda
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) : 1741 - 1747
  • [4] Pyridine Activation via Copper(I)-Catalyzed Annulation toward indolizines
    Barluenga, Jose
    Lonzi, Giacomo
    Riesgo, Lorena
    Lopez, Luis A.
    Tomas, Miguel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13200 - 13202
  • [5] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines
    Berman, Ashley M.
    Lewis, Jared C.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 14926 - +
  • [6] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines
    Bull, James A.
    Mousseau, James J.
    Pelletier, Guillaume
    Charette, Andre B.
    [J]. CHEMICAL REVIEWS, 2012, 112 (05) : 2642 - 2713
  • [7] Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines
    Cai, Zhong-Jian
    Wang, Shun-Yi
    Ji, Shun-Jun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2686 - 2692
  • [8] General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem
    Chernyak, Natalia
    Gevorgyan, Vladimir
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) : 2743 - 2746
  • [9] Recent progress in the pharmacology of imidazo[1,2-a]pyridines
    Enguehard-Gueiffier, Cecile
    Gueiffier, Alain
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (09) : 888 - 899
  • [10] Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C-H Functionalization
    Fischer, Daniel F.
    Sarpong, Richmond
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 5926 - +