Rh(III)-Catalyzed C-H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones

被引:11
作者
Shu, Bing [1 ]
Song, Jia-Lin [2 ]
Chen, Shao-Yong [2 ]
Zheng, Yi-Chuan [2 ]
Zhang, Shang-Shi [2 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China
[2] Guangdong Pharmaceut Univ, Ctr Drug Res & Dev, Guangzhou 510006, Peoples R China
基金
中国国家自然科学基金;
关键词
DERIVATIVES; ACTIVATION; PROBE; CINNOLINES; CATALYSIS; RH;
D O I
10.1021/acs.joc.2c02722
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh(III)-catalyzed C-H/N-H annulation and C- H allylation of phenylindazolones have been realized by employing 5-methylene-1,3-dioxan-2-one and 4-vinyl-1,3-dioxolan-2-one as scalable cross-coupling partners, delivering functionalized indazolone fused heterocycles and branched and linear allyl indazolones respectively in moderate to high yield. These divergent synthesis protocols showcase mild conditions, broad substrate scope, and high functional-group compatibility. In addition, scale-up synthesis and preliminary mechanistic exploratory were also accomplished.
引用
收藏
页码:3499 / 3508
页数:10
相关论文
共 48 条
  • [1] Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization
    Achar, Tapas Kumar
    Maiti, Sudip
    Jana, Sadhan
    Maiti, Debabrata
    [J]. ACS CATALYSIS, 2020, 10 (23) : 13748 - 13793
  • [2] Electrochemical synthesis of N,N′-disubstituted indazolin-3-ones via an intramolecular anodic dehydrogenative N-N coupling reaction
    Bieniek, Jessica C.
    Gruenewald, Michele
    Winter, Johannes
    Schollmeyer, Dieter
    Waldvogel, Siegfried R.
    [J]. CHEMICAL SCIENCE, 2022, 13 (27) : 8180 - 8186
  • [3] Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes
    Chen, Shao-Yong
    Zheng, Yi-Chuan
    Liu, Xu-Ge
    Song, Jia-Lin
    Shu, Bing
    Zheng, Tao
    Xiao, Lin
    Zhang, Shang-Shi
    Cao, Hua
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3302 - 3309
  • [4] Unparalleled Ease of Access to a Library of Biheteroaryl Fluorophores via Oxidative Cross-Coupling Reactions: Discovery of Photostable NIR Probe for Mitochondria
    Cheng, Yangyang
    Li, Gaocan
    Liu, Yang
    Shi, Yang
    Gao, Ge
    Wu, Di
    Lan, Jingbo
    You, Jingsong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) : 4730 - 4738
  • [5] Indazole derivatives and their therapeutic applications: a patent review (2013-2017)
    Denya, Ireen
    Malan, Sarel F.
    Joubert, Jacques
    [J]. EXPERT OPINION ON THERAPEUTIC PATENTS, 2018, 28 (06) : 441 - 453
  • [6] El-Hawash S. A. M., EUR J MED CHEM
  • [7] Synthesis of indazole motifs and their medicinal importance: An overview
    Gaikwad, Digambar D.
    Chapolikar, Archana D.
    Devkate, Chandrashekhar G.
    Warad, Khandu D.
    Tayade, Amit P.
    Pawar, Rajendra P.
    Domb, Abraham J.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 : 707 - 731
  • [8] Mild metal-catalyzed C-H activation: examples and concepts
    Gensch, T.
    Hopkinson, M. N.
    Glorius, F.
    Wencel-Delord, J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) : 2900 - 2936
  • [9] Indazole N-oxide derivatives as antiprotozoal agents:: Synthesis, biological evaluation and mechanism of action studies
    Gerpe, A
    Aguirre, G
    Boiani, L
    Cerecetto, H
    González, M
    Olea-Azar, C
    Rigol, C
    Maya, JD
    Morello, A
    Piro, OE
    Arán, VJ
    Azqueta, A
    de Ceráin, AL
    Monge, A
    Rojas, MA
    Yaluff, G
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (10) : 3467 - 3480
  • [10] Synthesis of quaternary carbon-centered indolo[1,2-a]quinazolinones and indazolo[1,2-a]indazolones via C-H functionalization
    Gogoi, Kongkona
    Bora, Bidisha R.
    Borah, Geetika
    Sarma, Bipul
    Gogoi, Sanjib
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (11) : 1388 - 1391