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
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 10期
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
  • [31] One-Pot Synthesis of 2,3-Disubstituted-2,3-dihydroquinazolin-4(1H)-ones Using [Hmim][NO3]: An Eco-Friendly Protocol
    Mohammadpoor-Baltork, Iraj
    Khosropour, Ahmad Reza
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Soltani, Mohammad
    Mirjafari, Arsalan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (06) : 1419 - 1427
  • [32] One-Pot Synthesis of 2,4-Disubstituted Indoles from N-Tosyl-2,3-dichloroaniline Using Palladium-Dihydroxyterphenylphosphine Catalyst
    Yamaguchi, Miyuki
    Manabe, Kei
    ORGANIC LETTERS, 2014, 16 (09) : 2386 - 2389
  • [33] Phosphomolybdic Acid (PMA)-catalyzed One-pot Synthesis of 2,3-Dihydroquinazolines
    Chen, Chuanhuan
    Xuejiao, A.
    Li, Xia
    Huang, Guoli
    Liu, Bo
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (08) : 683 - 687
  • [34] One-Pot Electro-Oxidative Annulation Reactions: Synthesis of Polysubstituted Pyrroles from Anilines and Alkynoates
    Shi, Guang
    Sun, Jie
    Chen, Zhiwei
    CHEMISTRYSELECT, 2021, 6 (44): : 12342 - 12345
  • [35] A Facile and Efficient One-Pot Synthesis of Substituted Quinolines from α-Arylamino Ketones Under Vilsmeier Conditions
    Wang, Yan
    Xin, Xin
    Liang, Yongjiu
    Lin, Yingjie
    Zhang, Rui
    Dong, Dewen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (24) : 4165 - 4169
  • [36] KSCN and K2CO3 mediated one-pot synthesis of cyclopropanyl coumarin derivatives
    Imrankhan, Mohammed
    Shivashankar, Kalegowda
    JOURNAL OF CHEMICAL SCIENCES, 2021, 133 (02)
  • [37] Triphosgene and Triphenylphosphine Oxide-Mediated Cascade Heterocyclization of N-Acylated Anilines: One-Pot Synthesis of 2,4-Dichloroquinolines
    Feng, Daming
    Xu, Changlin
    Wang, Wenhao
    Zhan, Haoming
    Ge, Chunhua
    Huang, Peng
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (20) : 14610 - 14618
  • [38] A Concise One-Pot Approach to the Synthesis of 4-(1H-Indol-3-yl)quinolines
    Arcadi, Antonio
    Chiarini, Marco
    Marinelli, Fabio
    Picchini, Silvia
    SYNTHESIS-STUTTGART, 2011, (24): : 4084 - 4090
  • [39] N-Heterocyclic Carbene Catalyzed One-Pot Synthesis of 2,3-Diarylquinoxalines
    Lin, Yang
    Lei, Xiaoli
    Yang, Qin
    Yuan, Jiangjun
    Ding, Qiuping
    Xu, Jingshi
    Peng, Yiyuan
    SYNTHESIS-STUTTGART, 2012, 44 (17): : 2699 - 2706
  • [40] Facile Synthesis of 2,3-Disubstituted Indoles by NBS/CuCl Mediated Oxidative Cyclization of N-Aryl Enamines
    Hu, Fang-Zhi
    Zhao, Si-Han
    Chen, Hui
    Yu, Shuo-Wen
    Xu, Xiao-Ying
    Yuan, Wei-Cheng
    Zhang, Xiao-Mei
    CHEMISTRYSELECT, 2017, 2 (04): : 1409 - 1412
12345