Visible-Light-Induced Multicomponent Synthesis of Tetrasubstituted Imidazoles

被引:1
|
作者
Borkotoky, Lodsna [1 ,2 ]
Bora, Kaushik [1 ,2 ]
Maurya, Ram Awatar [1 ,2 ]
机构
[1] North East Inst Sci & Technol NEIST, CSIR, Chem Sci & Technol Div, Appl Organ Chem Grp, Jorhat 785006, Assam, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India
关键词
2; 4-Dinitrophenol; Imidazole; Multicomponent reaction; Photocatalysis; Visible light; OXIDATIVE COUPLING REACTION; ALPHA-AMINOPHOSPHONATES; BIOLOGICAL EVALUATION; PHOTOREDOX CATALYSIS; AMIDINES SYNTHESIS; VINYL AZIDES; AMINES; ALDEHYDES/KETONES; CYCLIZATION;
D O I
10.1002/ajoc.202300146
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient visible light photocatalyzed one-pot, three-component synthesis of tetrasubstituted imidazoles was developed. Catalytic amount of 2,4-dinitrophenol (2,4-DNP) was necessary for the successful coupling of anilines, aldehydes and alpha-keto vinyl azides to yield imidazoles in the presence of 7 W blue LED light. The scope of the reaction was demonstrated by synthesizing a series of highly functionalized imidazoles in excellent yields (75-86%). Control experiments were carried out and a mechanistic rationalization of the three-component reaction was proposed.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Visible-Light-Induced Passerini Multicomponent Polymerization
    Tuten, Bryan T.
    De Keer, Lies
    Wiedbrauk, Sandra
    Van Steenberge, Paul H. M.
    D'hooge, Dagmar R.
    Barner-Kowollik, Christopher
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (17) : 5672 - 5676
  • [2] Visible-Light-Induced Synthesis of Branched Ethers via Multicomponent Reactions
    Gyorfi, Nandor
    Tasnadi, Gabor
    Gyuris, Mario
    Kotschy, Andras
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14): : 10014 - 10019
  • [3] Visible-Light-Induced Multicomponent Synthesis of γ-Amino Esters with Diazo Compounds
    Ma, Na
    Guo, Lin
    Qi, Dan
    Gao, Fei
    Yang, Chao
    Xia, Wujiong
    ORGANIC LETTERS, 2021, 23 (16) : 6278 - 6282
  • [4] Transition-metal-free, visible-light-induced multicomponent synthesis of allylic amines and tetrahydroquinolines
    Wang, Jian
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (13) : 3452 - 3459
  • [5] Visible-light-induced regioselective synthesis of polyheteroaromatic compounds
    Chatterjee, Tanmay
    Choi, Myung Gil
    Kim, Jun
    Chang, Suk-Kyu
    Cho, Eun Jin
    CHEMICAL COMMUNICATIONS, 2016, 52 (22) : 4203 - 4206
  • [6] Visible-Light-Induced Dearomatizations
    Okumura, Mikiko
    Sarlah, David
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1259 - 1273
  • [7] Visible-light-induced selectivity controllable synthesis of diamine or imidazoline derivatives by multicomponent decarboxylative radical coupling reactions
    Pan, Shulei
    Jiang, Min
    Zhong, Guofu
    Dai, Linlong
    Zhou, Yu
    Wei, Kaihang
    Zeng, Xiaofei
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (24): : 4043 - 4049
  • [8] Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans
    Lin, Run
    Sun, Hongnan
    Yang, Chao
    Yang, Youdong
    Zhao, Xinxin
    Xia, Wujiong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1 - 6
  • [9] De Novo Synthesis of Imidazoles by Visible-Light-Induced Photocatalytic Aerobic Oxidation/[3+2] Cycloaddition/Aromatization Cascade
    Deng, Qiao-Hui
    Zou, You-Quan
    Lu, Liang-Qiu
    Tang, Zi-Long
    Chen, Jia-Rong
    Xiao, Wen-Jing
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) : 2432 - 2435
  • [10] Visible-Light-Induced Aminochlorination of Alkenes
    Mejri, Emna
    Higashida, Kosuke
    Kondo, Yuta
    Nawachi, Anna
    Morimoto, Hiroyuki
    Ohshima, Takashi
    Sawamura, Masaya
    Shimizu, Yohei
    ORGANIC LETTERS, 2023, 25 (24) : 4581 - 4585