Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 2-benzylimidazo[1,2-a]pyridine

被引:62
作者
Bakherad, Mohammad [1 ]
Nasr-Isfahani, Hossein [1 ]
Keivanloo, Ali [1 ]
Doostmohammadi, Nesa [1 ]
机构
[1] Shahrood Univ Technol, Dept Chem, Sch Sci, Shahrood, Iran
关键词
Sonogashira coupling; aryl iodide; imidazole; Pd-catalyzed; imidazopyridines;
D O I
10.1016/j.tetlet.2008.03.141
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 2-amino-1-(2-propynyl)pyridinium bromide with various iodobenzenes, catalyzed by Pd-Cu, leads to the formation of 2-benzylimidazo[1,2-a]pyridines. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3819 / 3822
页数:4
相关论文
共 48 条
  • [1] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES
    ARCADI, A
    CACCHI, S
    MARINELLI, F
    [J]. TETRAHEDRON LETTERS, 1989, 30 (19) : 2581 - 2584
  • [2] A novel synthetic route to new 2-aryl-6-methyl[1,3,5]triazino[1,2-d] [1,3,4]thiadiazine-4,7(6H,9H)-dithiones
    Bakavoli, M
    Bakherad, M
    Heravi, MM
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (05) : 1157 - 1162
  • [3] Bates DK, 1999, HETEROCYCLES, V51, P475
  • [4] Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents
    Biftu, T
    Feng, D
    Fisher, M
    Liang, GB
    Qian, XX
    Scribner, A
    Dennis, R
    Lee, S
    Liberator, PA
    Brown, C
    Gurnett, A
    Leavitt, PS
    Thompson, D
    Mathew, J
    Misura, A
    Samaras, S
    Tamas, T
    Sina, JF
    McNulty, KA
    McKnight, CG
    Schmatz, DM
    Wyvratt, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (09) : 2479 - 2483
  • [5] Bouyssi D, 1997, SYNLETT, P944
  • [6] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications
    Bunz, UHF
    [J]. CHEMICAL REVIEWS, 2000, 100 (04) : 1605 - 1644
  • [7] 2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis:: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR
    Enguehard-Gueiffier, C
    Fauvelle, F
    Debouzy, JC
    Peinnequin, A
    Thery, I
    Dabouis, V
    Gueiffier, A
    [J]. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2005, 24 (2-3) : 219 - 227
  • [8] Sonogashira coupling reactions of highly oxygenated vinyl halides: The first synthesis of harveynone and epi-harveynone
    Graham, AE
    McKerrecher, D
    Davies, DH
    Taylor, RJK
    [J]. TETRAHEDRON LETTERS, 1996, 37 (41) : 7445 - 7448
  • [9] The chemistry of enediynes, enyne allenes and related compounds
    Grissom, JW
    Gunawardena, GU
    Klingberg, D
    Huang, DH
    [J]. TETRAHEDRON, 1996, 52 (19) : 6453 - 6518
  • [10] Imidazo[1,2-a]pyridines with potent activity against herpesviruses
    Gudmundsson, Kristian S.
    Johns, Brian A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (10) : 2735 - 2739