Facile, one-pot, four-component synthesis of a new series of imidazo[1,2-a]pyridines in presence of TPAB in EtOH under reflux conditions

被引:10
|
作者
Etivand, Nasser [1 ]
Khalafy, Jabbar [1 ]
Marjani, Ahmad Poursattar [1 ]
机构
[1] Urmia Univ, Dept Organ Chem, Fac Chem, Orumiyeh 5756151818, Iran
关键词
Imidazo[1; 2-a]pyridines; 2-Aminopyridine; Aryl glyoxal monohydrates; Ethyl acetoacetate; Hydrazine hydrate; One-pot four-component reaction; TPAB; MICROWAVE-ASSISTED SYNTHESIS; CATALYZED SYNTHESIS; DERIVATIVES; RECEPTOR; CONVENIENT; DISCOVERY; PYRIDINES; BINDING;
D O I
10.1007/s11164-019-03797-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient, regioselective, novel, and elegant one-pot, four-component reaction was designed for synthesis of a series of new of imidazo[1,2-a]pyridines using aryl glyoxal monohydrates, ethyl acetoacetate, hydrazine hydrate, and 2-aminopyridine in presence of tetrapropylammonium bromide under reflux in EtOH as solvent. The main advantages of this protocol include the availability and low cost of the starting materials, short reaction time, convenient operation, easy workup process, highly facile operation, nonhazardous byproducts, and high yield (82-94%). [GRAPHICS] .
引用
收藏
页码:3379 / 3394
页数:16
相关论文
共 50 条
  • [41] One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides
    Adib, Mehdi
    Sheikhi, Ehsan
    Rezaei, Narjes
    TETRAHEDRON LETTERS, 2011, 52 (25) : 3191 - 3194
  • [42] One-pot Synthesis of 3-Aminoimidazo[1,2-a]pyridines Catalyzed by Heteropolyacids
    Oskooie, Hossein A.
    Amini, Maryam
    Heravi, Majid M.
    Bamoharram, Fatemah F.
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (02) : 299 - 302
  • [43] ONE POT FUNCTIONALIZATION OF 3 AND 6 POSITIONS OF IMIDAZO[1,2-A]PYRIDINES UNDER MICROWAVE IRRADIATION
    Koubachi, J.
    El Kazzouli, S.
    Berteina-Raboin, S.
    Mouaddib, A.
    Guillaumet, G.
    SCIENTIFIC STUDY AND RESEARCH-CHEMISTRY AND CHEMICAL ENGINEERING BIOTECHNOLOGY FOOD INDUSTRY, 2006, 7 (04): : 895 - 898
  • [44] Indium triflate promoted one-pot multicomponent synthesis of structurally diverse 3-amino-imidazo[1,2-a]pyridines
    Swami, Suman
    Agarwala, Arunava
    Shrivastava, Rahul
    MOLECULAR DIVERSITY, 2017, 21 (01) : 81 - 88
  • [45] Indium triflate promoted one-pot multicomponent synthesis of structurally diverse 3-amino-imidazo[1,2-a]pyridines
    Suman Swami
    Arunava Agarwala
    Rahul Shrivastava
    Molecular Diversity, 2017, 21 : 81 - 88
  • [46] 2-Aminopyridines as an α-Bromination Shuttle in a Transition Metal-Free One-Pot Synthesis of Imidazo[1,2-a]pyridines
    Roslan, Irwan Iskandar
    Ng, Kian-Hong
    Chuah, Gaik-Khuan
    Jaenicke, Stephan
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) : 364 - 369
  • [47] One-pot Synthesis of Benzo[4,5]imidazo[1,2-a]pyridine Derivatives in Aqueous Conditions
    Vodolazhenko, Maria A.
    Mykhailenko, Anastasiia E.
    Gorobets, Nikolay Yu.
    Desenko, Sergey M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 753 - 757
  • [48] Microwave-assisted four-component, one-pot condensation reaction: an efficient synthesis of annulated pyridines
    Yan, Chao-Guo
    Cai, Xi-Mei
    Wang, Qi-Fang
    Wang, Ting-Yu
    Zheng, Ming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (06) : 945 - 951
  • [49] Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates
    Yadav, Lal Dhar S.
    Awasthi, Chhama
    CARBOHYDRATE RESEARCH, 2010, 345 (02) : 318 - 323
  • [50] A one-pot synthesis of 1,2-dihydroisoquinoline derivatives from isoquinoline via a four-component reaction
    Alizadeh, Abdolali
    Zohreh, Nasrin
    HELVETICA CHIMICA ACTA, 2008, 91 (05) : 844 - 849