Nano indium oxide catalyzed tandem cyclization of amidine with nitroolefin

被引:31
作者
Mitra, Shubhanjan [1 ]
Bagdi, Avik Kumar [1 ]
Majee, Adinath [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
Nano indium oxide; Imidazole; Nitroolefin; Amidine; Cyclization; ONE-POT SYNTHESIS; C-H; RECYCLABLE CATALYST; EFFICIENT; IMIDAZOLES; ACID; BENZIMIDAZOLES; CHEMISTRY; ALDEHYDES; CHLORIDE;
D O I
10.1016/j.tetlet.2013.07.050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A tandem cyclization of amidine with nitroolefin has been described using nano In2O3 as an efficient catalyst. The reaction is effective for the preparation of 4,5-unsymmetrically substituted 1-H imidazole in moderate to good yields. The catalyst was successfully reused for four consecutive cycles with similar catalytic activities. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4982 / 4985
页数:4
相关论文
共 57 条
  • [1] Palladium Nanoparticle-Catalyzed C-N Bond Formation. A Highly Regio- and Stereoselective Allylic Amination by Allyl Acetates
    Adak, Laksmikanta
    Chattopadhyay, Kalicharan
    Ranu, Brindaban C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3982 - 3985
  • [2] Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis
    Albrecht, Lukasz
    Dickmeiss, Gustav
    Acosta, Fabio Cruz
    Rodriguez-Escrich, Carles
    Davis, Rebecca L.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2543 - 2546
  • [3] Anwar S., 2013, CHEM EUR J
  • [4] Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes
    Arai, Takayoshi
    Mishiro, Asami
    Yokoyama, Naota
    Suzuki, Kuniko
    Sato, Hiroyasu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5338 - +
  • [5] F-block N-heterocyclic carbene complexes
    Arnold, Polly L.
    Liddle, Stephen T.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (38) : 3959 - 3971
  • [6] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis
    Astruc, D
    Lu, F
    Aranzaes, JR
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) : 7852 - 7872
  • [7] Nano indium oxide as a recyclable catalyst for the synthesis of arylaminotetrazoles
    Bahari, Siavash
    Sabegh, Mehdi Ahmadi
    [J]. JOURNAL OF CHEMICAL SCIENCES, 2013, 125 (01) : 153 - 157
  • [8] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry
    Basavaiah, Deevi
    Reddy, Bhavanam Sekhara
    Badsara, Satpal Singh
    [J]. CHEMICAL REVIEWS, 2010, 110 (09) : 5447 - 5674
  • [9] SULPHUR-METHYLENE ISOSTERISM IN DEVELOPMENT OF METIAMIDE, A NEW HISTAMINE H2-RECEPTOR ANTAGONIST
    BLACK, JW
    DURANT, GJ
    EMMETT, JC
    GANELLIN, CR
    [J]. NATURE, 1974, 248 (5443) : 65 - 67
  • [10] Stable carbenes
    Bourissou, D
    Guerret, O
    Gabbaï, FP
    Bertrand, G
    [J]. CHEMICAL REVIEWS, 2000, 100 (01) : 39 - 91