Sc(OTf)3-Mediated One-Pot Synthesis of 2,3-Disubstituted Quinolines from Anilines and Epoxides

被引:16
|
作者
Al Mehedi, Md Shafaat [1 ]
Tepe, Jetze J. [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48823 USA
基金
美国国家卫生研究院;
关键词
3-COMPONENT SYNTHESIS; FUNCTIONALIZATION; QUINAZOLINE; ANNULATION; ALDEHYDE; ACCESS; BONDS;
D O I
10.1021/acs.joc.0c00803
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, we report the first synthesis of 2,3-disubstituted quinolines from anilines and aromatic or aliphatic epoxides. This reaction utilizes Sc(OTf)(3) as a Lewis acid and TEMPO as an oxygen scavenger. A wide variety of highly substituted quinolines were obtained with moderate to excellent yields (up to 96%).
引用
收藏
页码:6741 / 6746
页数:6
相关论文
共 50 条
  • [1] Synthesis of 2,3-Disubstituted Indoles from α-Diketones and N-Substituted Anilines: One-Pot Pd-Catalyzed Reductive Amination
    Eliad Benitez-Medina, G.
    Amezquita-Valencia, Manuel
    Cabrera, Armando
    Sharma, Pankaj
    CHEMCATCHEM, 2017, 9 (08) : 1450 - 1460
  • [2] A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones
    Minoo Dabiri
    Peyman Salehi
    Mahboobeh Bahramnejad
    Mohsen Alizadeh
    Monatshefte für Chemie - Chemical Monthly, 2010, 141 : 877 - 881
  • [3] A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones
    Dabiri, Minoo
    Salehi, Peyman
    Bahramnejad, Mahboobeh
    Alizadeh, Mohsen
    MONATSHEFTE FUR CHEMIE, 2010, 141 (08): : 877 - 881
  • [4] Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
    Hue Thi Buu Bui
    Kiep Minh Do
    Huy Tran Duc Nguyen
    Hieu Van Mai
    Thanh La Duc Danh
    De Quang Tran
    Morita, Hiroyuki
    TETRAHEDRON, 2021, 98
  • [5] Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates
    Zhao, Hongyang
    Xing, Yanpeng
    Lu, Ping
    Wang, Yanguang
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (42) : 15144 - 15150
  • [6] Fe(OTf)3 Catalyzed Annulation of 2,3-Disubstituted Indoles with Aziridines
    Liu, Hua
    Zheng, Chao
    You, Shu-Li
    CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (08) : 709 - 714
  • [7] One-Pot Mannich, Aza-Wittig and Dehydrofluorinative Aromatization Reactions for Direct Synthesis of 2,3-Disubstituted 4-Aminoquinolines
    Zhang, Xiaofeng
    Ma, Xiaoming
    Qiu, Weiqi
    Awad, JohnMark
    Evans, Jason
    Zhang, Wei
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (23) : 5513 - 5517
  • [8] Metal-free sequential reaction via a propargylation, annulation and isomerization sequence for the one-pot synthesis of 2,3-disubstituted benzofurans
    Li, Wen-Tao
    Nan, Wen-Hui
    Luo, Qun-Li
    RSC ADVANCES, 2014, 4 (66) : 34774 - 34779
  • [9] Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans
    Sun, Manman
    Song, Jinyu
    Wang, Lei
    Yin, Wenguang
    Miao, Maozhong
    Ren, Hongjun
    SYNLETT, 2020, 31 (08) : 818 - 822
  • [10] Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols
    Tursky, Matyas
    Lorentz-Petersen, Linda L. R.
    Olsen, Lasse B.
    Madsen, Robert
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) : 5576 - 5582