Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization

被引：30
|
作者：
Dhiman, Shiv [1 ]
Saini, Hitesh Kumar [1 ]
Nandwana, Nitesh Kumar [1 ]
Kumar, Dalip [1 ]
Kumar, Anil [1 ]
机构：
[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
来源：
RSC ADVANCES | 2016年 / 6卷 / 29期
关键词：
INTRAMOLECULAR DIRECT ARYLATION; ONE-POT SYNTHESIS; SODIUM-AZIDE; GEM-DIBROMOVINYLANILINES; ACRIDONE ALKALOIDS; CASCADE REACTIONS; ARYL AZIDES; AGENTS; METAL; INHIBITORS;
D O I：
10.1039/c6ra03798d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel regioselective synthesis of 2-aminoquinolines and 2-arylquinoline-3-carbonitriles is described via copper-mediated tandem reaction. Formation of substituted quinolines involves Knoevenagel condensation of ortho-bromobenzaldehyde with active methylene nitriles followed by copper-catalyzed reductive amination and intramolecular cyclization.
引用
收藏
页码：23987 / 23994
页数：8
相关论文
共 50 条
  • [1] Facile Synthesis of Polysubstituted Oxazoles via A Copper-Catalyzed Tandem Oxidative Cyclization
    Wan, Changfeng
    Zhang, Jintang
    Wang, Sujing
    Fan, Jinmin
    Wang, Zhiyong
    ORGANIC LETTERS, 2010, 12 (10) : 2338 - 2341
  • [2] Nitrile Furanics via Copper-Catalyzed Dehydration of Aldoximes and Knoevenagel Condensation
    Annatelli, Mattia
    Sadraoui, Chaimaa
    Trapasso, Giacomo
    Arico, Fabio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (20)
  • [3] ORGN 24-Synthesis of polycyclic heteroaromatics by copper-catalyzed tandem amination and intramolecular electrophilic cyclization
    Verma, Akhilesh Kumar
    Kesharwani, Tanay
    Singh, Jaspal
    Tandon, Vibha
    Larock, Richard C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [4] An environmentally benign, green, and efficient ionic liquid catalyzed synthesis of Quinoline derivatives via Knoevenagel condensation
    Tasqeeruddin, Syed
    Asiri, Yahya, I
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (01) : 132 - 139
  • [5] Copper-catalyzed synthesis of benzoxazoles via tandem cyclization of 2-halophenols with amidines
    Tiwari, Abhishek R.
    Bhanage, Bhalchandra M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (33) : 7920 - 7926
  • [6] One-pot synthesis of polyfunctionalized quinolines via a copper-catalyzed tandem cyclization
    Chen, Dianpeng
    Sun, Xuejun
    Shan, Yingying
    You, Jinmao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (41) : 7657 - 7662
  • [7] Copper-catalyzed Tandem Cyclization to Access 4-Aminoquinoline Derivatives
    Sheng, Hui-Yang
    Chen, Hui
    Liao, Meng
    Peng, Na
    Yang, Mian
    Cai, Qun
    Liu, Yi
    CHEMISTRY LETTERS, 2020, 49 (05) : 526 - 529
  • [8] Copper-catalyzed four-component synthesis of imidazo[1,2-a]pyridines via sequential reductive amination, condensation, and cyclization
    Allahabadi, Emad
    Ebrahimi, Sina
    Soheilizad, Mehdi
    Khoshneviszadeh, Mehdi
    Mahdavi, Mohammad
    TETRAHEDRON LETTERS, 2017, 58 (02) : 121 - 124
  • [9] Copper-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation
    Ma, Peng
    Wang, Yuhang
    Wang, Jianhui
    Ma, Ning
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (19) : 9377 - 9382
  • [10] Synthesis of β-Allylbutenolides via One-Pot Copper-Catalyzed Hydroallylation/Cyclization of γ-Hydroxybutynoate Derivatives
    Yamamoto, Yoshihiko
    Shibano, Shinya
    Kurohara, Takashi
    Shibuya, Masatoshi
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4503 - 4511
12345