Graphene oxide: A carbocatalyst for the one-pot multicomponent synthesis of highly functionalized tetrahydropyridines

被引：24
|
作者：
Gupta, Annah [1 ]
Kaur, Ramneet [1 ]
Singh, Deepika [2 ]
Kapoor, Kamal K. [1 ]
机构：
[1] Univ Jammu, Dept Chem, Jammu 180006, India
[2] CSIR, Med Chem Div, Indian Inst Integrat Med, Canal Rd, Jammu 180001, India
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 26期
关键词：
Graphene oxide; Carbocatalyst; Multicomponent reaction; Tetrahydropyridine; Heterogeneous catalysis; One-pot reaction; GRAPHITE OXIDE; SUBSTITUTED PIPERIDINES; BETA-ENAMINONES; METAL-FREE; EFFICIENT; SOLVENT; DERIVATIVES; INHIBITORS; PYRIDINES; CHEMISTRY;
D O I：
10.1016/j.tetlet.2017.05.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple, straightforward and efficient methodology is described for the synthesis of polysubstituted tetrahydropyridine via one-pot multicomponent reaction of beta-ketoester, aldehyde and aniline in presence of catalytic amount of graphene oxide in acetonitrile. Graphene oxide is a versatile carbocatalyst and this is the first report on its application in a five component reaction. Good yield, usage of readily available starting material, operational simplicity, easy work-up and eco-friendly re-usable catalyst are the key features of this protocol. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2583 / 2587
页数：5
相关论文
共 50 条
  • [41] One-Pot Multicomponent Synthesis of β-Amino Amides
    Huang, Bo
    Zeng, Linwei
    Shen, Yangyong
    Cui, Sunliang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) : 4565 - 4568
  • [42] One-pot multicomponent synthesis of polysubstituted indolizines
    Mao, Zhenjun
    Li, Xuejian
    Lin, Xufeng
    Lu, Ping
    Wang, Yanguang
    [J]. TETRAHEDRON, 2012, 68 (01) : 85 - 91
  • [43] One-Pot, Multicomponent Sequential Synthesis of Benzothiazoloquinazolinones
    Sharma, Bhupesh K.
    Sharma, Praveen Kumar
    Kumar, M.
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (16) : 2347 - 2352
  • [44] Chemically Sustainable and Green One-Pot Multicomponent Synthesis of Highly Functionalized Polycyclic N-Fused-Pyrrolidine Heterocycles
    Yan, Li-Jun
    Wang, Jun-Liang
    Xu, Dan
    Burgess, Kevin S.
    Zhu, Ai-Fei
    Rao, Yan-Ying
    Chen, Xue-Bing
    Wang, Yong-Chao
    [J]. CHEMISTRYSELECT, 2018, 3 (02): : 662 - 665
  • [45] Facile and efficient synthesis of functionalized iminothiopyran and isothiochromen via one-pot multicomponent reactions
    Hamadi, Hosein
    Khoobi, Mehdi
    Hossaini, Zinatossadat
    Shafiee, Abbas
    [J]. MOLECULAR DIVERSITY, 2011, 15 (01) : 35 - 40
  • [46] Multicomponent one-pot synthesis of highly-functionalized pyrrole-3-carbonitriles in aqueous medium and their computational study
    Pagadala, Ramakanth
    Kommidi, Devendar Reddy
    Kankala, Shravankumar
    Maddila, Suresh
    Singh, Parvesh
    Moodley, Brenda
    Koorbanally, N. A.
    Jonnalagadda, Sreekantha B.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (06) : 1800 - 1806
  • [47] Facile and efficient synthesis of functionalized iminothiopyran and isothiochromen via one-pot multicomponent reactions
    Hosein Hamadi
    Mehdi Khoobi
    Zinatossadat Hossaini
    Abbas Shafiee
    [J]. Molecular Diversity, 2011, 15 : 35 - 40
  • [48] TRIPHENYLPHOSPHINE-CATALYZED, NOVEL, ONE-POT, MULTICOMPONENT SYNTHESIS OF FUNCTIONALIZED β-ACETAMIDO CARBONYLS
    Singh, Shyam Babu
    Verma, Pankaj Kumar
    Tiwari, Kamleshwar
    Singh, Mandavi
    Ankit, Preyas
    Fatma, Shahin
    Singh, Jagdamba
    Tiwari, Kamla Prasad
    [J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (12) : 1795 - 1802
  • [49] A one-pot synthesis of highly substituted tetrahydropyridines from N-benzylidenemethanamines, dialkyl acetylenedicarboxylates and benzylidenemalononitriles
    Mehrabi, Hossein
    Mohebbi, Ahmad
    [J]. ARKIVOC, 2016, : 89 - 100
  • [50] Eco-friendly one-pot synthesis of highly dispersible functionalized graphene nanosheets with free amino groups
    Liu, Zhiting
    Duan, Xuezhi
    Qian, Gang
    Zhou, Xinggui
    Yuan, Weikang
    [J]. NANOTECHNOLOGY, 2013, 24 (04)
12345