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
  • [31] Cooperative photoredox/gold catalysed cyclization of 2-alkynylbenzoates with arenediazonium salts: synthesis of 3,4-disubstituted isocoumarins
    Pirovano, Valentina
    Brambilla, Elisa
    Fanciullacci, Giorgia
    Abbiati, Giorgio
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (41) : 8065 - 8070
  • [32] Ionic Liquid - an Efficient Recyclable System for the Synthesis of 2,4-Disubstituted Quinolines via Meyer-Schuster Rearrangement
    Sarma, Rupam
    Prajapati, Dipak
    SYNLETT, 2008, (19) : 3001 - 3005
  • [33] Intramolecular Carbolithiation Reactions for the Synthesis of 2,4-Disubstituted Tetrahydro-quinolines: Evaluation of TMEDA and (-)-Sparteine as Ligands in the Stereoselectivity
    Martinez-Estibalez, Unai
    Sotomayor, Nuria
    Lete, Esther
    ORGANIC LETTERS, 2009, 11 (06) : 1237 - 1240
  • [34] One-pot regioselective synthesis of 2,4-disubstituted quinolines via copper(II)-catalyzed cascade annulation
    Wu, Wenhao
    Guo, Yujuan
    Xu, Xuefeng
    Zhou, Zhi
    Zhang, Xu
    Wu, Bo
    Yi, Wei
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1713 - 1718
  • [35] Synthesis of 2-Halogenated Quinolines by Halide-Mediated Intramolecular Cyclization of o-Alkynylaryl Isocyanides
    Mitamura, Takenori
    Nomoto, Akihiro
    Sonoda, Motohiro
    Ogawa, Akiya
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2010, 83 (07) : 822 - 824
  • [36] Synthesis of diastereomeric 2,4-disubstituted pyrano[2,3-b]quinolines from 3-formyl-2-quinolones through O-C bond formation via intramolecular electrophilic cyclization
    Singh, Mrityunjay K.
    Chandra, Atish
    Singh, Bhawana
    Singh, Radhey M.
    TETRAHEDRON LETTERS, 2007, 48 (34) : 5987 - 5990
  • [37] Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents
    Patel, Sanjay R.
    Gangwal, Rahul
    Sangamwar, Abhay T.
    Jain, Rahul
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 93 : 511 - 522
  • [38] SYNTHESIS OF 2-(1-NONENYL)-4-QUINOLINOL)PYO 3) + SOME RELATED 2,4-DISUBSTITUTED QUINOLINES
    GOTTSTEIN, WJ
    CHENEY, LC
    ROBERTS, H
    WELLS, IC
    JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10): : 3065 - +
  • [39] Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of o-Alkynylaryl Isocyanides with Iodine
    Mitamura, Takenori
    Ogawa, Akiya
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (04): : 1163 - 1166
  • [40] Microwave-assisted one-pot synthesis of 2,4-disubstituted quinolines under solvent-free conditions
    Yadav, JS
    Reddy, BVS
    Rao, RS
    Naveenkumar, V
    Nagaiah, K
    SYNTHESIS-STUTTGART, 2003, (10): : 1610 - 1614