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
  • [1] 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
    Nasser Etivand
    Jabbar Khalafy
    Ahmad Poursattar Marjani
    Research on Chemical Intermediates, 2019, 45 : 3379 - 3394
  • [2] An Efficient One-Pot Four-Component Synthesis of Functionalized Imidazo[1,2-a]pyridines
    Movahed, Siyavash Kazemi
    Dabiri, Minoo
    Bazgir, Ayoob
    HELVETICA CHIMICA ACTA, 2013, 96 (03) : 525 - 532
  • [3] A one-pot four-component synthesis of pyrrolo[1,2-a]quinolines
    Adib, Mehdi
    Azimzadeh, Marjan
    Rahimi-Nasrabadi, Mehdi
    Zhu, Long-Guan
    JOURNAL OF CHEMICAL RESEARCH, 2014, (07) : 423 - 426
  • [4] Novel one-pot pseudo four component reaction: expeditious synthesis of functionalized imidazo[1,2-a]pyridines
    Sanaeishoar, Haleh
    Nazarpour, Roya
    Mohave, Fouad
    RSC ADVANCES, 2015, 5 (84) : 68571 - 68578
  • [5] Simple synthesis of benzo[g]imidazo[1,2-a]quinolinedione derivatives via a one-pot, four-component reaction
    Bayat, Mohammad
    Hosseini, Fahimeh
    Notash, Behrouz
    TETRAHEDRON LETTERS, 2016, 57 (49) : 5439 - 5441
  • [6] Ammonium chloride catalyzed one-pot synthesis of imidazo[1,2-a]pyridines
    Shaabani, Ahmad
    Rezazadeh, Fahimeh
    Soleimani, Ebrahim
    MONATSHEFTE FUR CHEMIE, 2008, 139 (08): : 931 - 933
  • [7] Ammonium chloride catalyzed one-pot synthesis of imidazo[1,2-a]pyridines
    Ahmad Shaabani
    Fahimeh Rezazadeh
    Ebrahim Soleimani
    Monatshefte für Chemie - Chemical Monthly, 2008, 139 : 931 - 933
  • [8] One-pot synthesis of new imidazo[1,2-a] pyridine and imidazo[1,2-a]pyrimidine derivatives
    Georgescu, F
    Georgescu, E
    Draghici, C
    Iuhas, PC
    Filip, PI
    REVUE ROUMAINE DE CHIMIE, 2005, 50 (05) : 349 - 352
  • [9] InBr3-catalyzed three-component, one-pot synthesis of imidazo[1,2-a]pyridines
    Reddy, B. V. Subba
    Reddy, P. Sivaramakrishna
    Reddy, Y. Jayasudhan
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2011, 52 (44) : 5789 - 5793
  • [10] (Bromodimethylsulfonium) Bromide-Catalyzed One-Pot Three-Component Synthesis of Imidazo[1,2-a]pyridines
    Venkatesham, R.
    Manjula, A.
    Rao, B. Vittal
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (04) : 942 - 947