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

被引:15
|
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 Indanone Derivatives in Water under Exogenous Ligand-Free and Mild Conditions
    Zhu, Anqiao
    Sun, Yu
    Lai, Jingru
    Chen, Ziyan
    Bu, Xiaoli
    Yue, Yan-Ni
    Ma, Mengtao
    Xue, Fei
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12): : 7884 - 7894
  • [32] Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization
    Reddy, Chada Raji
    Krishna, Gaddam
    Kavitha, Nerella
    Latha, Bellamkonda
    Shin, Dong-Soo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (27) : 5381 - 5388
  • [33] Base-mediated sequential one-pot approach for the synthesis of 2,3-disubstituted indoles from 2-(tosylamino)aryl-substituted para-quinone methides
    Pandey, Rajat
    Singh, Gurdeep
    Gour, Vinod
    Anand, Ramasamy Vijaya
    TETRAHEDRON, 2021, 82
  • [34] Nickel-Catalyzed One-Pot Carbonylative Synthesis of 2-Mono- and 2,3-Disubstituted Thiochromenones from 2-Bromobenzenesulfonyl Chlorides and Alkynes
    Wang, Wei
    Bao, Zhi-Peng
    Qi, Xinxin
    Wu, Xiao-Feng
    ORGANIC LETTERS, 2021, 23 (16) : 6589 - 6593
  • [35] One-pot access to 2,3-disubstituted 1,2,3,4-tetrahydroquinolines by reductive amination of aldehydes with sodium cyanoborohydride
    Lewin, G
    Schaeffer, C
    HETEROCYCLES, 1998, 48 (01) : 171 - 174
  • [36] ONE-POT SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF PYRANO [2,3-b] QUINOLINES AND KHAPLOFOLINE
    Balamani, J.
    Velmurugan, R.
    Sekar, M.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 20 (01) : 73 - 76
  • [37] 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
  • [38] Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions
    Markina, Nataliya A.
    Chen, Yu
    Larock, Richard C.
    TETRAHEDRON, 2013, 69 (13) : 2701 - 2713
  • [39] DBSA catalyzed, one-pot three-component "on water" green protocol for the synthesis of 2,3-disubstituted 4-thiazolidinones
    Prasad, Davinder
    Preetam, Amreeta
    Nath, Mahendra
    RSC ADVANCES, 2012, 2 (07) : 3133 - 3140
  • [40] 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