Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene

被引：0
|
作者：
Yao Zhou
Fuling Chen
Ziru Li
Junjie Dong
Jingnan Li
Bohao Zhang
Qiuling Song
机构：
[1] Hubei Normal University,Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering
[2] Fujian Province University,Key Laboratory of Molecule Synthesis and Function Discovery
[3] College of Chemistry at Fuzhou University,undefined
来源：
Science China Chemistry | 2023年 / 66卷
关键词：
indazoles; skeletal editing; difluorocarbene; N−N bond cleavage; quinazolin-4(3; )-ones;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A novel difluorocarbene promoted single-atom skeletal editing of 2H-indazoles is demonstrated herein. Ethyl bromodifluoroacetate was severed as the difluorocarbene source in the current protocol, facilitating the cleavage of the N−N bond via carbon atom insertion. This metal-free ring expansion reaction enables the late-stage diversification of indazole skeletons, assembling a diverse array of functionalized quinazolin-4(3H)-ones in decent yields with excellent functional group compatibility.
引用
收藏
页码：1975 / 1981
页数：6
相关论文
共 50 条
  • [21] Direct C3 Carbamoylation of 2H-Indazoles
    Bhat, Vighneshwar Shridhar
    Lee, Anna
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (23) : 3382 - 3385
  • [22] A new effective route for the synthesis of substituted 2h-indazoles
    S. S. Mochalov
    M. I. Khasanov
    E. V. Trofimova
    A. N. Fedotov
    N. S. Zefirov
    [J]. Chemistry of Heterocyclic Compounds, 2009, 45 : 1208 - 1217
  • [23] Electrochemically promoted C-3 amination of 2H-indazoles
    Sun, Mingli
    Zhou, Yuhui
    Li, Laiqiang
    Wang, Lei
    Ma, Yongmin
    Li, Pinhua
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (04) : 754 - 759
  • [24] Inhibition of myeloperoxidase: Evaluation of 2H-indazoles and 1H-indazolones
    Roth, Aaron
    Ott, Sean
    Farber, Kelli M.
    Palazzo, Teresa A.
    Conrad, Wayne E.
    Haddadin, Makhluf J.
    Tantillo, Dean J.
    Cross, Carroll E.
    Eiserich, Jason P.
    Kurth, Mark J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (22) : 6422 - 6429
  • [25] Recent synthetic approaches to 1H- and 2H-indazoles (microreview)
    Rai, Gaurav S.
    Maru, Jayesh J.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 973 - 975
  • [26] Synthesis of 2H-Indazoles by the [3+2] Cycloaddition of Arynes and Sydnones
    Wu, Chunrui
    Fang, Yuesi
    Larock, Richard C.
    Shi, Feng
    [J]. ORGANIC LETTERS, 2010, 12 (10) : 2234 - 2237
  • [27] Remote difunctionalization of 2H-indazoles using Koser's reagents
    Bhattacharjee, Suvam
    Laru, Sudip
    Hajra, Alakananda
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (07) : 981 - 984
  • [28] Single-Atom Heat Machines Enabled by Energy Quantization
    Gelbwaser-Klimovsky, David
    Bylinskii, Alexei
    Gangloff, Dorian
    Islam, Rajibul
    Aspuru-Guzik, Alan
    Vuletic, Vladan
    [J]. PHYSICAL REVIEW LETTERS, 2018, 120 (17)
  • [29] Organophotoredox-Catalyzed Direct C-H Amination of 2H-Indazoles with Amines
    Neogi, Sukanya
    Ghosh, Asim Kumar
    Majhi, Koushik
    Samanta, Sadhanendu
    Kibriya, Golam
    Hajra, Alakananda
    [J]. ORGANIC LETTERS, 2020, 22 (14) : 5605 - 5609
  • [30] Benzylic C-H heteroarylation of 4-Methylphenols with 2H-Indazoles
    Yuan, Cheng
    Chen, Dongdong
    Pan, Changduo
    Yu, Jin-Tao
    [J]. TETRAHEDRON LETTERS, 2022, 105
12345