A novel atom-economic synthesis of functionalized imidazolidines through copper(I)-catalyzed domino three-component coupling and cyclization reactions

被引:12
|
作者
Li, Yufeng [1 ]
Wu, Zhengguang [1 ]
Shi, Jie [1 ]
Bu, Hongzhong [1 ]
Gu, Jiachao [1 ]
Pan, Yi [2 ]
机构
[1] Nanjing Tech Univ, Coll Sci, Nanjing 211816, Jiangsu, Peoples R China
[2] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China
关键词
Alkynes; Cyclization; Imines; Multicomponent reactions; Nitrogen heterocycles; N-HETEROCYCLIC CARBENES; MULTICOMPONENT REACTIONS; NITROGEN-HETEROCYCLES; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; RING; ALKYNES; IMINES; 2-PYRIDINECARBOXALDEHYDE; PROPARGYLAMINES;
D O I
10.1016/j.tet.2014.03.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An interesting approach to functionalized imidazolidines is described. These compounds are obtained in a copper(l)-catalyzed domino three-component coupling and cyclization reaction involving two formaldehyde-derived imine units and a terminal alkyne. Alternatively, imidazolidines can be obtained from propargylamines and formaldehyde-derived imines. This strategy provides a straightforward and atom-economic pathway to construct imidazolidines with high yields and benefits from readily available starting materials, convenient one-pot operations. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3134 / 3140
页数:7
相关论文
共 50 条
  • [31] One pot synthesis of indene through copper(I)-catalyzed three-components coupling and cyclization reaction
    Wang, Xiang-Chuan
    Zhong, Mei-Jin
    Liang, Yong-Min
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) : 3636 - 3641
  • [32] Facile Atom-Economic Synthesis of Ammonium Diselenophosphinates via Three-Component Reaction of Secondary Phosphines, Elemental Selenium, and Ammonia
    Artem'ev, Alexander V.
    Malysheva, Svetlana F.
    Gusarova, Nina K.
    Belogorlova, Nataliya A.
    Trofimov, Boris A.
    [J]. SYNTHESIS-STUTTGART, 2010, (11): : 1777 - 1780
  • [33] Sequential coupling-isomerization-coupling reactions -: A novel three-component synthesis of aryl chalcones
    Liao, Wei-Wei
    Mueller, Thomas J. J.
    [J]. SYNLETT, 2006, (20) : 3469 - 3473
  • [34] Synthesis of indole-fused 1,4-diazepines through domino three-component coupling-cyclization-N-arylation by copper catalysis under microwave irradiation
    Ohta, Yusuke
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [35] Stereoselective Synthesis of Functionalized 1,3-Enynes through Recyclable Copper(I)-Catalyzed Three-Component Reaction of Terminal Alkynes, Diazoesters and Aldehydes
    Ye, Qian
    Liao, Yang
    Luo, Chengkai
    Cai, Mingzhong
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (05)
  • [36] Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine
    Zeng, Suwei
    Xu, Sen
    Wang, Yong
    Yu, Min
    Zhu, Li
    Yao, Xiaoquan
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (04) : 827 - 834
  • [37] Domino Condensation/S-Arylation/Heterocyclization Reactions: Copper-Catalyzed Three-Component Synthesis of 2-N-Substituted Benzothiazoles
    Ma, Dawei
    Lu, Xu
    Shi, Liu
    Zhang, Hui
    Jiang, Yongwen
    Liu, Xiangqian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 1118 - 1121
  • [38] Montmorillonite clay-catalyzed reactions: A facile synthesis of three-component coupling homoallylic amines
    Yadav, JS
    Reddy, BVS
    Raju, AK
    Gnaneshwar, D
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (09) : 938 - 940
  • [39] Cu-Mn spinel oxide catalyzed synthesis of imidazo[1,2-a]pyridines through domino three-component coupling and 5-exo-dig cyclization in water
    Bharate, Jaideep B.
    Guru, Santosh K.
    Jain, Shreyans K.
    Meena, Samdarshi
    Singh, Parvinder Pal
    Bhushan, Shashi
    Singh, Baldev
    Bharate, Sandip B.
    Vishwakarma, Ram A.
    [J]. RSC ADVANCES, 2013, 3 (43): : 20869 - 20876
  • [40] Synthesis of Novel Aliphatic N-sulfonylamidino Thymine Derivatives by Cu(I)-catalyzed Three-component Coupling Reaction
    Krstulovic, Luka
    Ismaili, Hamit
    Bajic, Miroslav
    Visnievac, Aleksandar
    Glavas-Obrovac, Ljubica
    Zinic, Biserka
    [J]. CROATICA CHEMICA ACTA, 2012, 85 (04) : 525 - 534