Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

被引：4
|
作者：
Huang, Peng-Fei [1 ]
Fu, Jia-Le [1 ]
Huang, Jia-Jing [1 ]
Xiong, Bi-Quan [1 ]
Tang, Ke-Wen [1 ]
Liu, Yu [1 ]
机构：
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 03期
基金：
中国国家自然科学基金;
关键词：
MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; LIGHT; ISONITRILES; CATALYSIS; INSERTION;
D O I：
10.1039/d3ob01915b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We herein report an efficient photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access a wide range of 2,4-disubstituted quinolines. Preliminary mechanism experiment results suggested that this reaction was initiated by an acyl radical generated from acyl chlorides through a single-electron-transfer (SET) process. This transformation showed good substrate suitability and functional group compatibility at room temperature.
引用
收藏
页码：513 / 520
页数：8
相关论文
共 38 条
  • [1] Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines
    Gao, Mei-Jin
    Ding, Chuan
    Huang, Peng-Fei
    Xie, Rong
    Liu, Yu
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (13): : 4571 - 4579
  • [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] 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
  • [4] 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
  • [5] Facile Synthesis of 2,4-Disubstituted Thiooxazoles and 2,4-Disubstituted Oxazole Sulfonyl Chlorides via Acyl Isothiocyanates and TMS-Diazomethane
    Trujillo, John I.
    Arnold, Eric P.
    Kortum, Steve
    Robinson, Ralph P.
    SYNLETT, 2015, 26 (12) : 1764 - 1768
  • [6] 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
  • [7] 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
  • [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] Synthesis and radical cyclization of 2-allylamino-3-chloropropylphenyl sulfones to 2,4-disubstituted pyrrolidines
    Giovannini, R
    Petrini, M
    SYNLETT, 1998, (01) : 90 - +
  • [10] Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o- hydroxycinnamaldehydes: synthesis of 2,4-disubstituted chromans
    Maity, Rajendra
    Pan, Subhas Chandra
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (09) : 1598 - 1608
1234