Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines

被引:0
|
作者
Gao, Mei-Jin [1 ]
Ding, Chuan [1 ]
Huang, Peng-Fei [1 ]
Xie, Rong [1 ]
Liu, Yu [1 ]
机构
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 13期
基金
中国国家自然科学基金;
关键词
DOEBNER-VON MILLER; BIOLOGICAL EVALUATION; EFFICIENT; DERIVATIVES; ACCESS;
D O I
10.1021/acs.joc.4c03121
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, a photochemical radical cyclization reaction of o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as aryl radical precursors at room temperature. This approach allowed good functional group tolerance and substrate applicability.
引用
收藏
页码:4571 / 4579
页数:9
相关论文
共 50 条
  • [1] Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines
    Huang, Peng-Fei
    Fu, Jia-Le
    Huang, Jia-Jing
    Xiong, Bi-Quan
    Tang, Ke-Wen
    Liu, Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (03) : 513 - 520
  • [2] Visible-light-induced synthesis of 2,4-disubstituted quinolines from o-vinylaryl isocyanides and oxime esters
    Liu, Yu
    Ding, Chuan
    Huang, Jia-Jing
    Zhou, Quan
    Xiong, Bi-Quan
    Tang, Ke-Wen
    Huang, Peng-Fei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (07) : 1458 - 1465
  • [3] Iodine-Mediated Regioselective Radical Cyclization of o-Vinylaryl Isocyanides with Disulfides/Diselenides Leading to 2-Chalcogenated Quinolines
    Li, Ya-Nan
    Chen, Fan
    Zhang, Xing-Guo
    Tu, Hai-Yong
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3814 - 3818
  • [4] Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
    Liu, Yan
    Li, Shi-Jun
    Chen, Xiao-Lan
    Fan, Lu-Lu
    Li, Xiao-Yun
    Zhu, Shan-Shan
    Qu, Ling-Bo
    Yu, Bing
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 688 - 694
  • [5] An efficient synthesis of novel 2,4-disubstituted tetrahydroquinolines and quinolines
    Devakaram, Ruth
    Black, David StC
    Kumar, Naresh
    TETRAHEDRON LETTERS, 2012, 53 (18) : 2269 - 2272
  • [6] Synthesis of 2,4-Disubstituted Quinolines in Deep Eutectic Solvents
    Chen, Guoqing
    Xie, Zongbo
    Liu, Yishuai
    Meng, Jia
    Le, Zhanggao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (01) : 156 - 161
  • [7] Synthesis and anti-tuberculosis activity of 2,4-disubstituted quinolines
    Nayyart, Amit
    Jain, Rahul
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (01): : 117 - 128
  • [8] Synthesis of 2,4-disubstituted quinolines by reactions of o-isocyano-β-methoxystyrene derivatives with organolithiums
    Kobayashi, K
    Yoneda, K
    Mano, M
    Morikawa, O
    Konishi, H
    CHEMISTRY LETTERS, 2003, 32 (01) : 76 - 77
  • [9] An efficient synthesis of 2,4-disubstituted quinolines by electrophile-mediated cyclization reactions of 2-isocyanostyrene derivatives
    Kobayashi, K
    Takagoshi, K
    Kondo, S
    Morikawa, O
    Konishi, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (03) : 553 - 559
  • [10] ORGN 994-Tandem reduction/cyclization of o-nitrophenyl propargyl alcohols: Facile synthesis of 2,4-disubstituted quinolines
    Sandelier, Matthew J.
    DeShong, Philip
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234