Copper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2H-Indazoles

被引:0
|
作者
Manas, Clara [1 ,2 ]
Herrero-Bourdieu, Juan [1 ]
Merino, Estibaliz [1 ,2 ]
机构
[1] Univ Alcala, Inst Invest Andres M Rio IQAR, Fac Farm, Dept Quim Organ & Quim Inorgan, Alcala De Henares 28805, Madrid, Spain
[2] Inst Ramon & Cajal Invest Sanitaria IRYCIS, Madrid 28034, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 22期
关键词
SUBSTITUTED CINNOLINES; CYCLIZATION; COARCTATE; INDAZOLES; PSEUDOCOARCTATE; 2H-INDAZOLES; COMPLEXES;
D O I
10.1021/acs.joc.4c02144
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C-N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step. Further derivatization enables functionalization of the 3-alkenyl-2H-indazoles.
引用
收藏
页码:16883 / 16888
页数:6
相关论文
共 50 条
  • [1] Combined Gold and Photoredox Catalysis: Synthesis of 3-Alkenyl-2H-Indazoles from 2-Alkynylazobenzenes
    Manas, Clara
    Merino, Estibaliz
    ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (01)
  • [2] Asymmetric Synthesis of Chiral Chromanes by Copper-Catalyzed Hydroamination of 2H-Chromenes
    Yang, Qingjing
    Li, Sifeng
    Wang, Jun
    CHEMCATCHEM, 2020, 12 (12) : 3202 - 3206
  • [3] A DFT study of the mechanism of copper-catalyzed synthesis of 2H-indazoles from aryl azide
    Li, Juan
    Zhang, Qi
    Wu, Caihong
    Gu, Honghong
    Yan, Bo
    DALTON TRANSACTIONS, 2014, 43 (01) : 55 - 62
  • [4] Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols
    Oshimoto, Kohei
    Tsuji, Hiroaki
    Kawatsura, Motoi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (17) : 4225 - 4229
  • [5] Ionic liquid-supported copper-catalyzed synthesis of 2H-indazoles under microwave irradiation
    Dasmahapatra, Upala
    Chanda, Kaushik
    Maiti, Barnali
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (05) : 761 - 770
  • [6] Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination
    Ichikawa, Saki
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2019, 21 (21) : 8736 - 8739
  • [7] Enantioselective Synthesis of α-Aminosilanes by Copper-Catalyzed Hydroamination of Vinylsilanes
    Niljianskul, Nootaree
    Zhu, Shaolin
    Buchwald, Stephen L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) : 1638 - 1641
  • [8] Synthesis of α-Aminophosphines by Copper-Catalyzed Regioselective Hydroamination of Vinylphosphines
    Takata, Tatsuaki
    Nishikawa, Daiki
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (43) : 10975 - 10978
  • [9] Synthesis of 2-Alkenyl-2H-indazoles from 2-(2-Carbonylmethyl)-2H-indazoles
    Lin, Mei-Huey
    Liang, Kung-Yu
    Tsai, Chang-Hsien
    Chen, Yu-Chun
    Hsiao, Hung-Chang
    Li, Yi-Syuan
    Chen, Chung-Hao
    Wu, Hau-Chun
    MOLECULES, 2016, 21 (02)
  • [10] Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines
    Tsuhako, Akiko
    Oikawa, Daisuke
    Sakai, Kazushi
    Okamoto, Sentaro
    TETRAHEDRON LETTERS, 2008, 49 (46) : 6529 - 6532