N-heterocyclic carbomethoxylation catalyzed by ionic liquids in the presence of dimethyl carbonate

被引:37
作者
Fu, Xianlei [1 ]
Zhang, Zhan [1 ]
Li, Caimeng [1 ]
Wang, Libing [1 ]
Ji, Haiying [1 ]
Yang, Yu [1 ]
Zou, Ting [1 ]
Gao, Guohua [1 ]
机构
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
Dimethyl carbonate; Ionic liquid; Carbamates; Mechanism; NUCLEOPHILIC CATALYSIS; ALIPHATIC-AMINES; CARBOXYLIC-ACIDS; AROMATIC-AMINES; EFFICIENT; ESTERIFICATION; METHYLATION; NITROGEN; METHANOL; ACCESS;
D O I
10.1016/j.catcom.2008.11.012
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A procedure for the synthesis of N-heterocyclic carbamates from N-heterocycles and dimethyl carbonate catalyzed by ionic liquids was investigated. [Bmim]OH was found to be the most active catalyst among the applied ionic liquids. Effects of the amount of ionic liquid, reaction temperature and the reusability of ionic liquid were also investigated. Ninety six percentage yield and 100% selectivity were obtained under the optimal conditions when using indole as a reactant. Additionally, [Bmim]OH can be reused at least up to four times without any decrease of activity. The possible reaction mechanism was discussed based on the reaction results. (c) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:665 / 668
页数:4
相关论文
共 33 条
  • [1] The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids
    Aggarwal, A
    Lancaster, NL
    Sethi, AR
    Welton, T
    [J]. GREEN CHEMISTRY, 2002, 4 (05) : 517 - 520
  • [2] ACTIVATION AND COUPLING OF PYRROLE-1-CARBOXYLIC ACID IN THE FORMATION OF PYRROLE N-CARBONYL COMPOUNDS - PYRROLE-1-CARBOXYLIC ACID ANHYDRIDE
    BOGER, DL
    PATEL, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) : 2319 - 2323
  • [3] An acidity scale of 1,3-dialkylimidazolium salts in dimethyl sulfoxide solution
    Chu, Yuan
    Deng, Hui
    Cheng, Jin-Pei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) : 7790 - 7793
  • [4] Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts
    Cole, AC
    Jensen, JL
    Ntai, I
    Tran, KLT
    Weaver, KJ
    Forbes, DC
    Davis, JH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5962 - 5963
  • [5] Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis
    Curini, M
    Epifano, F
    Maltese, F
    Rosati, O
    [J]. TETRAHEDRON LETTERS, 2002, 43 (28) : 4895 - 4897
  • [6] FLACHSMANN JP, 2006, Patent No. 2006039822
  • [7] Ultrasound promoted acetylation of alcohols in room temperature ionic liquid under ambient conditions
    Gholap, AR
    Venkatesan, K
    Daniel, T
    Lahoti, RJ
    Srinivasan, KV
    [J]. GREEN CHEMISTRY, 2003, 5 (06) : 693 - 696
  • [8] Synthesis of dimethyl carbonate from methanol and carbon dioxide in the presence of polyoxometalates under mild conditions
    Jiang, CJ
    Guo, YH
    Wang, CG
    Hu, CW
    Wu, Y
    Wang, EB
    [J]. APPLIED CATALYSIS A-GENERAL, 2003, 256 (1-2) : 203 - 212
  • [9] Vanadium-catalyzed selective aerobic alcohol oxidation in ionic liquid [bmim]PF6
    Jiang, Nan
    Ragauskas, Arthur J.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (02) : 273 - 276
  • [10] Ionic liquid catalyzed Henry reactions
    Jiang, T
    Gao, HX
    Han, BX
    Zhao, GY
    Chang, YH
    Wu, WZ
    Gao, L
    Yang, GY
    [J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2699 - 2701