Fast condensation of cyclohexanone with 2-aminobenzonitrile at room temperature catalysed by an N-heterocyclic carbene

被引:8
|
作者
Zhen, Bin [1 ]
Jiao, Qingze [1 ]
Zhang, Yaping [1 ]
Wu, Qin [1 ]
Li, Hansheng [1 ]
Shi, Daxin [1 ]
Li, Jiarong [1 ]
机构
[1] Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
关键词
N-heterocyclic carbene; Quinazolinone; Condensation; Cyclohexanone; 2-Aminobenzonitrile; ACID;
D O I
10.1016/j.catcom.2012.11.029
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 fast condensation of cyclohexanone with 2-aminobenzonitrile catalysed by N-heterocyclic carbene 1,3-dipropylimidazole-2-ylidene (NHC-PPIm) at room temperature was discovered. NHC-PPIm was prepared via concentration of a 1,3-dipropylimidazolium hydroxide aqueous solution and showed excellent catalytic activity in the condensation reaction for the synthesis of quinazolinone. A possible catalytic mechanism was proposed based on the umpolung of cyclohexanone. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:1 / 4
页数:4
相关论文
共 50 条
  • [1] N-Heterocyclic carbene catalysed β-lactam synthesis
    Duguet, Nicolas
    Campbell, Craig D.
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (06) : 1108 - 1113
  • [2] An Efficient Protocol for Palladium N-Heterocyclic Carbene-Catalysed Suzuki-Miyaura Reaction at room temperature
    Akkoc, Mitat
    Imik, Fatma
    Yasar, Sedat
    Dorcet, Vincent
    Roisnel, Thiery
    Bruneau, Christian
    Ozdemir, Ismail
    CHEMISTRYSELECT, 2017, 2 (20): : 5729 - 5734
  • [3] N-heterocyclic carbene-catalysed pentafluorophenylation of aldehydes
    Du, Guang-Fen
    Xing, Fen
    Gu, Cheng-Zhi
    Dai, Bin
    He, Lin
    RSC ADVANCES, 2015, 5 (45): : 35513 - 35517
  • [4] N-Heterocyclic carbene-catalysed synthesis of polyurethanes
    Coutelier, Olivier
    El Ezzi, Mohammad
    Destarac, Mathias
    Bonnette, Fabien
    Kato, Tsuyoshi
    Baceiredo, Antoine
    Sivasankarapillai, Gopakumar
    Gnanou, Yves
    Taton, Daniel
    POLYMER CHEMISTRY, 2012, 3 (03) : 605 - 608
  • [5] An N-heterocyclic carbene functional covalent organic framework for Knoevenagel condensation reaction and γ-butyrolactone synthesis at room temperature
    Zhang, Wenyao
    Wang, Biying
    Feng, Shulei
    Feng, Huijun
    Bai, Junhua
    Wang, Junwen
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (38) : 16813 - 16819
  • [6] N-heterocyclic carbene-catalysed Peterson olefination reaction
    Wang, Ying
    Du, Guang-Fen
    Gu, Cheng-Zhi
    Xing, Fen
    Dai, Bin
    He, Lin
    TETRAHEDRON, 2016, 72 (04) : 472 - 478
  • [7] N-heterocyclic carbene catalysed oxidative esterification of aliphatic aldehydes
    Samanta, Ramesh C.
    Studer, Armido
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (08): : 936 - 939
  • [8] N-Heterocyclic carbene-mediated redox condensation of alcohols
    Kato, Terumasa
    Matsuoka, Shin-ichi
    Suzuki, Masato
    CHEMICAL COMMUNICATIONS, 2016, 52 (55) : 8569 - 8572
  • [9] N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
    Candish, Lisa
    Levens, Alison
    Lupton, David W.
    CHEMICAL SCIENCE, 2015, 6 (04) : 2366 - 2370
  • [10] N-Heterocyclic carbene-catalysed intermolecular Stetter reactions of acetaldehyde
    Kim, Sun Min
    Jin, Ming Yu
    Kim, Mi Jin
    Cui, Yan
    Kim, Young Sug
    Zhang, Liqiu
    Song, Choong Eui
    Ryu, Do Hyun
    Yang, Jung Woon
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) : 2069 - 2071