N-methylpyrrolidine as an effective organocatalyst for the regioselective synthesis of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones

被引:3
|
作者
Habashi, Bayram Parsa [1 ]
Marjani, Ahmad Poursattar [1 ]
机构
[1] Urmia Univ, Fac Chem, Dept Organ Chem, Orumiyeh, Iran
关键词
Aryl glyoxal monohydrates (AG hydrates); Catalyst; 1H-imidazo[1,2-a] imidazol-2(3H)-ones; Guanidine hydrochloride; N-methylpyrrolidine; ONE-POT; EFFICIENT;
D O I
10.1007/s11164-022-04717-6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Methylpyrrolidine catalyzed, concise and attractive synthesis of a new class of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones was attained with impressive yields, in the presence of EtOH as a solvent, by means of a convenient and elegant condensation reaction between different aryl glyoxal monohydrates and guanidine hydrochloride under reflux conditions. Some specific merits of the current procedure, including encompasses low operating cost, availability of the starting substrates, reasonable reaction times, high reaction yield, operational simplicity, cleaner reaction profile, no harmful by-products, and the isolated product is in pure form. Structures of all the freshly synthesized products have been deduced by their FT-IR, H-1-NMR, C-13- NMR, Mass spectrometry data and microanalysis. [GRAPHICS] .
引用
收藏
页码:2325 / 2336
页数:12
相关论文
共 50 条
  • [1] N-methylpyrrolidine as an effective organocatalyst for the regioselective synthesis of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones
    Bayram Parsa Habashi
    Ahmad Poursattar Marjani
    Research on Chemical Intermediates, 2022, 48 (6) : 2325 - 2336
  • [2] Solid phase synthesis of [3,5,7]-1H-imidazo[1,5-a]imidazol-2(3H)-ones
    Yu, YP
    El Abdellaoui, HM
    Ostresh, JM
    Houghten, RA
    TETRAHEDRON LETTERS, 2001, 42 (04) : 623 - 625
  • [3] Synthesis and reactions of 1-hydroxy-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-ones
    Martynaitis, Vytas
    Steponaviciute, Rasa
    Krikstolaityte, Sonata
    Solovjova, Joana
    Mangelinckx, Sven
    De Kimpe, Norbert
    Holzer, Wolfgang
    Sackus, Algirdas
    TETRAHEDRON, 2011, 67 (21) : 3945 - 3953
  • [4] Synthesis and SAR of 1-hydroxy-1H-benzo[d] imidazol-2(3H)-ones as inhibitors of Damino acid oxidase
    Berry, James F.
    Ferraris, Dana
    Duvall, Bridget
    Hin, Niyada
    Rais, Rana
    Alt, Jesse
    Thomas, Ajit
    Rojas, Camilo
    Slusher, Barbara
    Tsukamoto, Takashi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [5] Synthesis of 1-aryl-4,5-diphenyl-1H-imidazol-2(3H)-ones
    Baranov, V. V.
    Rusak, V. V.
    Kravchenko, A. N.
    RUSSIAN CHEMICAL BULLETIN, 2022, 71 (09) : 2016 - 2020
  • [6] Synthesis of 1-aryl-4,5-diphenyl-1H-imidazol-2(3H)-ones
    V. V. Baranov
    V. V. Rusak
    A. N. Kravchenko
    Russian Chemical Bulletin, 2022, 71 : 2016 - 2020
  • [7] Synthesis and SAR of 1-Hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase
    Berry, James F.
    Ferraris, Dana V.
    Duvall, Bridget
    Hin, Niyada
    Rais, Rana
    Alt, Jesse
    Thomas, Ajit G.
    Rojas, Camilo
    Hashimoto, Kenji
    Slusher, Barbara S.
    Tsukamoto, Takashi
    ACS MEDICINAL CHEMISTRY LETTERS, 2012, 3 (10): : 839 - 843
  • [8] SYNTHESIS OF 2,3-DIHYDRO-1H-IMIDAZO [1,2-A] [1,3,5] BENZOTRIAZEPIN-5/6H/- ONES AND 2,3-DIHYDRO-1H-IMIDAZO[1,2-A][1,3,5] BENZOTRIAZEPIN-5/6H-THIONES
    DOLESCHA.G
    HORNYAK, G
    AGAI, B
    SIMIG, G
    FETTER, J
    LEMPERT, K
    TETRAHEDRON LETTERS, 1973, (51) : 5069 - 5072
  • [9] Efficient synthesis of imidazo[1,2-a]pyridin-3(2H)-ones
    Adib, Mehdi
    Mahdavi, Mohammad
    Abbasi, Alireza
    Jahromi, Amin Haghighat
    Bijanzadeh, Hamid Reza
    TETRAHEDRON LETTERS, 2007, 48 (18) : 3217 - 3220
  • [10] 2-Aryl-3-arylaminoisoxazol-5(2H)-ones as sources of indoles and imidazo[1,2-a]pyridines
    Jeffery, D
    Prager, RH
    Turner, D
    Dreimanis, M
    TETRAHEDRON, 2002, 58 (50) : 9965 - 9972