Easy synthesis of imidazo[1,5-a]indol-3-ones through Rh(iii)-catalyzed C-H allenylation/annulation

被引:19
作者
Zhu, Bin [1 ]
Yao, Zhenyu [1 ]
Huang, Lang [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Key Lab Precis Med & Mol Diag Fujian Univ, Key Lab Xiamen Marine & Gene Drugs,Minist Educ, Engn Res Ctr Mol Med,Key Lab Fujian Mol Med,Sch B, Xiamen 361021, Peoples R China
关键词
PROPARGYL ALCOHOLS; CARBENOID FUNCTIONALIZATION; DIRECTING GROUP; 4+1 ANNULATION; N BOND; ACTIVATION; BENZAMIDES; 2-ALKENYLPHENOLS; ISOINDOLINONES; CONSTRUCTION;
D O I
10.1039/d1cc04359e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient and regioselective synthesis of imidazo[1,5-a]indol-3-ones has been developed via a sequential C-H allenylation/annulation starting from easily available N-methoxycarbamoyl indoles and propargyl alcohols, in which the propargyl alcohols served as a C1 synthon. This strategy displays excellent regioselectivity, high atom economy and tolerates a broad substrate scope.
引用
收藏
页码:12012 / 12015
页数:4
相关论文
共 65 条
  • [1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
    Ackermann, Lutz
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
  • [2] Design and synthesis of indole and tetrahydroisoquinoline hydantoin derivatives as human chymase inhibitors
    Alagille, D
    Pfeiffer, B
    Scalbert, E
    Ferry, G
    Boutin, JA
    Renard, P
    Viaud-Massuard, MC
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2004, 19 (02) : 137 - 143
  • [3] Cascade C-H Functionalization/Amidation Reaction for Synthesis of Azepinone Derivatives
    Bai, Peng
    Huang, Xing-Fen
    Xu, Guo-Dong
    Huang, Zhi-Zhen
    [J]. ORGANIC LETTERS, 2016, 18 (13) : 3058 - 3061
  • [4] Ruthenium Oxidase Catalysis for Site-Selective C-H Alkenylations with Ambient O2 as the Sole Oxidant
    Bechtoldt, Alexander
    Tirler, Carina
    Raghuvanshi, Keshav
    Warratz, Svenja
    Kornhaass, Christoph
    Ackermann, Lutz
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) : 264 - 267
  • [5] Rhodium-Catalyzed (5+1) Annulations Between 2-Alkenylphenols and Allenes: A Practical Entry to 2,2-Disubstituted 2H-Chromenes
    Casanova, Noelia
    Seoane, Andres
    Mascarenas, Jose L.
    Gulias, Moises
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (08) : 2374 - 2377
  • [6] Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation
    Chen, Junyu
    Zhong, Tianshuo
    Zheng, Xiangyun
    Yin, Chuanliu
    Zhang, Lei
    Zhou, Jian
    Jiang, Xinpeng
    Yu, Chuanming
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 446 - 452
  • [7] Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds
    Chen, Xun
    Xie, Ying
    Xiao, Xinsheng
    Li, Guoqiang
    Deng, Yuanfu
    Jiang, Huanfeng
    Zeng, Wei
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (83) : 15328 - 15331
  • [8] K2S2O8-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines
    Chen, Zhichao
    Zhang, Hong
    Zhou, Shufeng
    Cui, Xiuling
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (11) : 3866 - 3872
  • [9] Rh(III)-catalyzed C-H activation/[4+3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones
    Cui, Sunliang
    Zhang, Yan
    Wang, Dahai
    Wu, Qifan
    [J]. CHEMICAL SCIENCE, 2013, 4 (10) : 3912 - 3916
  • [10] Metal-Catalyzed Annulations through Activation and Cleavage of C-H Bonds
    Gulias, Moises
    Luis Mascarenas, Jose
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) : 11000 - 11019