One pot imino Diels-Alder reaction for the synthesis of 3-aryl-3,4-dihydrobenzo[f]quinoline derivatives catalyzed by antimony trichloride

被引:17
|
作者
Maiti, Gourhari [1 ]
Karmakar, Rajiv [1 ]
Kayal, Utpal [1 ]
机构
[1] Jadavpur Univ, Dept Chem, Kolkata 700032, India
关键词
Naphthylamine; But-2-ynedioate; Imino Diels-Alder reaction; Multicomponent reaction; 3-Aryl-3,4 dihydrobenzoquinoline-1,2-dicarboxylate; Antimony trichloride; MULTICOMPONENT REACTIONS; ANTIMICROBIAL ACTIVITY; EFFICIENT; ROUTE; CHEMISTRY; LIBRARIES; PYRANO; MILD;
D O I
10.1016/j.tetlet.2013.03.093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An one pot simple and efficient approach toward the synthesis of dialkyl-3-aryl-3,4-dihydrobenzo[f]quinoline-1,2-dicarboxylate and its dehydro derivatives have been developed through the three-component reaction of aromatic aldehydes, 2-naphthylamine, and but-2-ynedioate catalyzed by SbCl3 under reflux in acetonitrile in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2920 / 2923
页数:4
相关论文
共 50 条
  • [21] Yb(OTf)3-catalyzed intermolecular imino Diels-Alder reaction of 2-azetidinone-tethered aryl imines as azadienes
    Ramesh, E
    Elamparuthi, E
    Raghunathan, R
    SYNTHETIC COMMUNICATIONS, 2006, 36 (10) : 1431 - 1436
  • [22] FeCl3-Catalyzed Synthesis of 2-Methyl-4-Substituted-1,2,3,4-Tetrahydroquinoline Derivatives by the Imino Diels-Alder Reaction
    Chen, Ye
    Lee, Yong Rok
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (07): : 2485 - 2488
  • [23] Inter- and intramolecular imino Diels-Alder reactions catalyzed by sulfamic acid: A mild and efficient catalyst for a one-pot synthesis of tetrahydroquinolines
    Nagarajan, R
    Magesh, CJ
    Perumal, PT
    SYNTHESIS-STUTTGART, 2004, (01): : 69 - 74
  • [24] A simple synthesis of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B
    Castro-Castillo, Vicente
    Suarez-Rozas, Cristian
    Simpson, Sebastian
    Barriga-Gonzalez, Andres
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (05) : 553 - 559
  • [25] A simple synthesis of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B
    Vicente Castro-Castillo
    Cristian Suárez-Rozas
    Sebastián Simpson
    Andrés Barriga-González
    Chemistry of Heterocyclic Compounds, 2017, 53 : 553 - 559
  • [26] A convenient and efficient process for the synthesis of 9-aryl-6,9-dihydro-1H-pyrazolo[3,4-f] quinoline-8-carbonitrile and 1-aryl-1,4-dihydrobenzo[f]quinoline-2-carbonitrile derivatives
    Zhang, Wen-Ting
    Niu, Fu-Xiang
    Yue, Rui-Xue
    Zhang, Yi
    Ma, Chen
    Sun, Jian
    Rong, Liangce
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (03) : 543 - 554
  • [27] Yb(OTf)3: an efficient catalyst for the synthesis of 3-arylbenzo [f]quinoline-1,2-dicarboxylate derivatives via imino-Diels-Alder reaction
    Wang, Xiang-Shan
    Zhou, Jie
    Yang, Ke
    Yao, Chang-Sheng
    TETRAHEDRON LETTERS, 2010, 51 (43) : 5721 - 5723
  • [28] Lewis acid promoted imino Diels-Alder reactions of 5-dienyl pyrimidinones with N-aryl/naphthyl imines:: synthesis of novel quinoline/benzoquinoline derivatives
    Bhargava, Gaurav
    Mohan, Chander
    Mahajan, Mohinder P.
    TETRAHEDRON, 2008, 64 (13) : 3017 - 3024
  • [29] Ball-milling Synthesis of Tetrahydroquinolinesvia'One-pot' Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid
    Wang Zeyou
    Shen Guodong
    Huang Xianqiang
    Gong Shuwen
    Yang Bingchuan
    Sun Zhenzhen
    Zhang Zuhao
    Liu Wanxing
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2020, 36 (05) : 835 - 842
  • [30] Intramolecular Diels-Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles
    Alizadeh, Abdolali
    Asalemi, Kaveh Amir Ashjaee
    Halvagar, Mohammadreza
    SYNTHESIS-STUTTGART, 2019, 51 (15): : 2936 - 2944