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
来源：
CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 90期
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
  • [31] Rhodium(III)-catalyzed intermolecular cyclization of anilines with sulfoxonium ylides toward indoles
    Shen, Zhihao
    Pi, Chao
    Cui, Xiuling
    Wu, Yangjie
    [J]. CHINESE CHEMICAL LETTERS, 2019, 30 (07) : 1374 - 1378
  • [32] Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds
    Shi, Zhuangzhi
    Koester, Dennis C.
    Boultadakis-Arapinis, Melissa
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (33) : 12204 - 12207
  • [33] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
  • [34] Transition Metal-Catalyzed Intermolecular Cascade C-H Activation/Annulation Processes for the Synthesis of Polycycles
    Song, Liangliang
    Van der Eycken, Erik V.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (01) : 121 - 144
  • [35] N-Methoxybenzamide: A Versatile Directing Group for Palladium-, Rhodium- and Ruthenium-Catalyzed C-H Bond Activations
    Subhedar, Dnyaneshwar D.
    Mishra, Ashish A.
    Bhanage, Bhalchandra M.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) : 4149 - 4195
  • [36] Cobalt-Catalyzed sp2-C-H Activation: Intermolecular Heterocyclization with Allenes at Room Temperature
    Thrimurtulu, Neetipalli
    Dey, Arnab
    Maiti, Debabrata
    Volla, Chandra M. R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) : 12361 - 12365
  • [37] syn-Selective Rhodium(I)-Catalyzed Allylations of Ketimines Proceeding through a Directed C-H Activation/Allene Addition Sequence
    Tran, Duc N.
    Cramer, Nicolai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) : 8181 - 8184
  • [38] Rhodium-Catalyzed Regioselective Synthesis of Isoindolium Salts from 2-Arylpyridines and Alkenes in Aqueous Medium under Oxygen
    Upadhyay, Nitinkumar Satyadev
    Jayakumar, Jayachandran
    Cheng, Chien-Hong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (21) : 3381 - 3386
  • [39] Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
    Vaitla, Janakiram
    Bayer, Annette
    Hopmann, Kathrin H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4277 - 4281
  • [40] Varasi M., 1995, International Patent, Patent No. [WO9532204A1, 9532204]
1234567