L-Proline catalyzed domino Michael addition of N-substituted anilines

被引：16
|
作者：
Deb, Mohit L. [1 ]
Deka, Bhaskar [1 ]
Rahman, Iftakur [1 ]
Baruah, Pranjal K. [1 ]
机构：
[1] Gauhati Univ, GUIST, Dept Appl Sci, Gauhati 781014, Assam, India
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 50期
关键词：
N-substituted aniline; L-Proline; Michael addition; Domino reaction; Room temperature; MULTICOMPONENT SYNTHESIS; DRUG DISCOVERY; INDOLES; DERIVATIVES; CHEMISTRY; EFFICIENT; KETONES; KINASE;
D O I：
10.1016/j.tetlet.2018.11.004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Here we report L-proline catalyzed 3-component reaction of indoles, aldehydes and N-substituted anilines in water as solvent at room temperature for the synthesis of 3-(alpha,alpha-diarylmethyl)indoles. The reaction is in fact a Michael addition of N-substituted anilines to alkylideneindolenines. The reaction is very clean, high yielding and having broad substrate scope. A tentative mechanism is proposed. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4430 / 4433
页数：4
相关论文
共 50 条
  • [1] L-Proline Catalyzed Synthesis of Various N-substituted Urea and Unsymmetrical N,N′-disubstituted Urea
    Nagarkar, Ajit G.
    Telvekar, Vikas N.
    LETTERS IN ORGANIC CHEMISTRY, 2018, 15 (11) : 926 - 930
  • [2] An Improved Practical Route to (±)-Epibatidine through L-Proline Catalyzed Intramolecular Michael Addition
    Huang Xiangui
    Shi Hongwei
    Ren Jiangmeng
    Liu Guixia
    Tang Yun
    Zeng Bubing
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (06) : 1305 - 1309
  • [3] Asymmetric Michael addition of malonate anions to prochiral acceptors catalyzed by L-proline rubidium salt
    Yamaguchi, M
    Shiraishi, T
    Hirama, M
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10): : 3520 - 3530
  • [4] Domino synthesis of fused hexacyclic imidazoquinolinoacridinones catalyzed by CuI/L-proline
    Li, Chao
    Zhang, Wen-Ting
    Wang, Xiang-Shan
    TETRAHEDRON, 2014, 70 (46) : 8919 - 8924
  • [5] EPIMERIC N-SUBSTITUTED L-PROLINE DERIVATIVES AS CHIRAL SELECTORS FOR LIGAND-EXCHANGE CHROMATOGRAPHY
    VEIGL, E
    LINDNER, W
    JOURNAL OF CHROMATOGRAPHY A, 1994, 660 (1-2) : 255 - 268
  • [6] A Convenient Methodology for Nitro-Michael Addition of Carbonyl Compounds Catalyzed by L-Proline Using Microwave Heating
    Russo, Alessio
    Leadbeater, Nicholas E.
    Lattanzi, Alessandra
    LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (02) : 98 - 102
  • [7] L-proline-catalyzed asymmetric aldol condensation of N-substituted isatins with acetone
    Chen, Gang
    Wang, Ye
    He, Hongping
    Gao, Suo
    Yang, Xiaosheng
    Hao, Xiaojiang
    HETEROCYCLES, 2006, 68 (11) : 2327 - 2333
  • [8] L-proline anchored hydrotalcite clays: An efficient catalyst for asymmetric Michael addition
    Vijaikumar, S.
    Dhakshinamoorthy, A.
    Pitchumani, K.
    APPLIED CATALYSIS A-GENERAL, 2008, 340 (01) : 25 - 32
  • [9] Asymmetric Michael Reaction Catalyzed by Proline Lithium Salt: Efficient Synthesis of L-Proline and Isoindoloisoquinolinone Derivatives
    Xu, Kun
    Zhang, Sheng
    Hu, Yanbin
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (11) : 3573 - 3578
  • [10] A three-component synthesis of N-substituted quinoline-3-carbonitrile derivatives catalysed by L-proline
    Shi, Chunling
    Chen, Hui
    Li, Yan
    Shi, Daqing
    Ji, Min
    JOURNAL OF CHEMICAL RESEARCH, 2008, (09) : 534 - 537
12345