Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones

被引:105
|
作者
Li, Pan [1 ]
Zhao, Jingjing [1 ]
Wu, Chunrui [1 ]
Larock, Richard C. [2 ]
Shi, Feng [1 ]
机构
[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Peoples R China
[2] Iowa State Univ, Dept Chem, Ames, IA 50010 USA
基金
中国国家自然科学基金;
关键词
BAMFORD-STEVENS REACTION; GENERATED IN-SITU; DIAZO-COMPOUNDS; 1,3-DIPOLAR CYCLOADDITION; 1H-INDAZOLES; DERIVATIVES; SELECTIVITY; SALTS;
D O I
10.1021/ol201086g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo compounds and arynes.
引用
收藏
页码:3340 / 3343
页数:4
相关论文
共 50 条
  • [31] Metal free coupling of heteroaryl N-tosylhydrazones and thiols: Efficient synthesis of sulfides
    Alfredo Garcia-Carrillo, Mario
    Guzman, Angel
    Diaz, Eduardo
    TETRAHEDRON LETTERS, 2017, 58 (20) : 1952 - 1956
  • [32] Copper-Mediated Synthesis of 1,2,3-Triazoles from N-Tosylhydrazones and Anilines
    Chen, Zhengkai
    Yan, Qiangqiang
    Liu, Zhanxiang
    Xu, Yiming
    Zhang, Yuhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13324 - 13328
  • [33] Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine
    Inamoto, Kiyofumi
    Katsuno, Mika
    Yoshino, Takashi
    Arai, Yukari
    Hiroya, Kou
    Sakamoto, Takao
    TETRAHEDRON, 2007, 63 (12) : 2695 - 2711
  • [34] Palladium-Catalyzed Oxidative CrossCoupling of N-Tosylhydrazones with Indoles: Synthesis of N-Vinylindoles
    Zeng, Xiaobao
    Cheng, Guolin
    Shen, Jinhai
    Cui, Xiuling
    ORGANIC LETTERS, 2013, 15 (12) : 3022 - 3025
  • [35] Transition-Metal-Free Synthesis of Polysubstituted Cyclopropane Derivatives from N-Tosylhydrazones and their Cytotoxic Activities
    Lawson, Marie
    Bignon, Jerome
    Brion, Jean-Daniel
    Hamze, Abdallah
    Alami, Mouad
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (10) : 1144 - 1154
  • [36] Regioselective Synthesis of Highly Functionalized Pyrazoles from N-Tosylhydrazones (vol 21, pg 1917, 2019 )
    Zhang, Qian
    Tang, Meng
    ORGANIC LETTERS, 2023, 25 (39) : 7268 - 7269
  • [37] FACILE REDOX FORMATION OF A 3-SUBSTITUTED MALEIMIDE FROM A 3-SUBSTITUTED N-HYDROXYSUCCINIMIDE
    GROUTAS, WC
    VENKATARAMAN, R
    BRUBAKER, MJ
    TAGUSAGAWA, F
    TETRAHEDRON LETTERS, 1991, 32 (43) : 6093 - 6096
  • [38] Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes
    Zhang, Kena
    Provot, Olivier
    Alami, Mouad
    Tran, Christine
    Hamze, Abdallah
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (02): : 1249 - 1261
  • [39] Palladium-catalyzed coupling of N-tosylhydrazones with ortho substituted aryl halides: synthesis of 4-arylchromenes and related heterocycles
    Rasolofonjatovo, Evelia
    Treguier, Bret
    Provot, Olivier
    Hamze, Abdallah
    Morvan, Estelle
    Brion, Jean-Daniel
    Alami, Mouad
    TETRAHEDRON LETTERS, 2011, 52 (09) : 1036 - 1040
  • [40] Synthesis of Trifluoromethylated Cycloheptatrienes from N-Tosylhydrazones: Transition-Metal-Free Buchner Ring Expansion
    Zhang, Zhikun
    Feng, Jiajie
    Xu, Yan
    Zhang, Songnan
    Ye, Yuxuan
    Li, Tianjiao
    Wang, Xi
    Chen, Jun
    Zhang, Yan
    Wang, Jianbo
    SYNLETT, 2015, 26 (01) : 59 - 62