Metal-Free Synthesis of Functionalized Quinolines from 2-Styrylanilines and 2-Methylbenzothiazoles/2-Methylquinolines

被引：2
|
作者：
Liu, Xiaoying [1 ]
Chu, Xianglong [1 ]
机构：
[1] Xinjiang Normal Univ, Sch Chem & Chem Engn, Urumqi 830054, Peoples R China
来源：
ACS OMEGA | 2023年 / 8卷 / 07期
关键词：
BOND FUNCTIONALIZATION; NITROGEN-HETEROCYCLES; POLYSUBSTITUTED QUINOLINES; QUINAZOLINE; CYCLIZATION; CLEAVAGE; ADJACENT; PYRIDINE; ECONOMY; OXYGEN;
D O I：
10.1021/acsomega.2c07736
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile functionalization of C(sp3)-H bonds and tandem cyclization strategy to synthesize quinoline derivatives from 2-methylbenzothiazoles or 2-methylquinolines and 2styrylanilines has been developed. This work avoids the requirement for transition metals, offering a mild approach to activation of C(sp(3))-H bonds and formation of new C-C and C-N bonds. This strategy features excellent functional group tolerance and scaled-up synthetic capability, thus providing an efficient and environmentally friendly access to medicinally valuable quinolines.
引用
收藏
页码：6940 / 6944
页数：5
相关论文
共 50 条
  • [41] Transition-metal-free synthesis of quinolines from 2-nitrobenzyl alcohol in water
    Zhu, Meijuan
    Wang, Chao
    Tang, Weijun
    Xiao, Jianliang
    TETRAHEDRON LETTERS, 2015, 56 (48) : 6758 - 6761
  • [42] Metal-free synthesis of 1,2,3-benzotriazines
    Jin-Yang Chen
    Ying-Wu Lin
    Wei-Min He
    Chinese Chemical Letters, 2020, 31 (12) : 2989 - 2990
  • [43] Potential antineoplastics. Synthesis and cytotoxicity of certain 4-chloro-3-(2-chloroethyl)-2-methylquinolines and related derivatives
    Badawey, ESAM
    Kappe, T
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (10) : 815 - 822
  • [44] New method for the synthesis of β-tropolones:: Structures of condensation products of o-quinones with 2-methylquinolines and the mechanism of their formation
    Minkin, V. I.
    Aldoshin, S. M.
    Komissarov, V. N.
    Dorogan, I. V.
    Sayapin, Yu. A.
    Tkachev, V. V.
    Starikov, A. G.
    RUSSIAN CHEMICAL BULLETIN, 2006, 55 (11) : 2032 - 2055
  • [45] New method for the synthesis of β-tropolones: Structures of condensation products of o-quinones with 2-methylquinolines and the mechanism of their formation
    V. I. Minkin
    S. M. Aldoshin
    V. N. Komissarov
    I. V. Dorogan
    Yu. A. Sayapin
    V. V. Tkachev
    A. G. Starikov
    Russian Chemical Bulletin, 2006, 55 : 2032 - 2055
  • [46] Metal-free cascade synthesis of unsymmetrical 2-aminopyrimidines from imidazolate enaminones
    Cui, Xue
    Ma, Jianting
    Zeng, Tingting
    Xu, Junyu
    Li, Youbin
    Wang, Xuesong
    RSC ADVANCES, 2021, 11 (39) : 24247 - 24253
  • [47] Metal-Free Synthesis of Cyclic and Acyclic Carbonates from CO2 and Alcohols
    Lim, Yu Na
    Lee, Chan
    Jang, Hye-Young
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (09) : 1823 - 1826
  • [48] Metal-Free Synthesis of 2-Aminothiazole Functionalized Imidazo[1,2-a]pyridines as Antibacterial Agents
    Devi, Sushma
    Sharma, Ankita
    Karoshi, Veeresh
    Kumar, Sunil
    Kumar, Ajay
    Sindhu, Jayant
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 34 (01) : 23 - 34
  • [49] Fast Transition Metal-Free Synthesis of Functionalized Oxindoles and Dihydroquinoline-2-ones Under Microwave Irradiation
    Couto, Julia L.
    Hornink, Milene M.
    Nascimento, Vinicius R.
    Andrade, Leandro H.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (44)
  • [50] Metal-Free Radical [2+2+1] Cyclization of ortho-Cyanoarylacrylamides with Alkyl Nitriles: Synthesis of Pyrrolo[3,2-c]quinolines
    Yang, Tao
    Xia, Wen-Jin
    Shang, Jia-Qi
    Li, Yi
    Wang, Xiang-Xiang
    Sun, Meng
    Li, Ya-Min
    ORGANIC LETTERS, 2019, 21 (02) : 444 - 447
12345