Construction of Pyrrolocoumarin Cores through Double C-H Annulation Cascade

被引：7
|
作者：
Michikita, Ryudai [1 ]
Usuki, Yoshinosuke [1 ]
Satoh, Tetsuya [1 ]
机构：
[1] Osaka City Univ, Dept Chem, Grad Sch Sci, Sumiyoshi Ku, 3-3-138 Sugimoto, Osaka 5588585, Japan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 22期
关键词：
Annulation; C-C coupling; C-H activation; Homogeneous catalysis; Rhodium; CATALYZED OXIDATIVE COUPLING/CYCLIZATION; LAMELLARIN ALKALOIDS; COUPLING REACTIONS; INTERNAL ALKYNES; ACTIVATION; FUNCTIONALIZATION; CLEAVAGE; BENZYLAMINES; BENZAMIDES;
D O I：
10.1002/ejoc.202200550
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rhodium(III)-catalyzed double C-H annulation of 3-(acetylamino)coumarins with internal arylacetylenes is reported. The reaction proceeds smoothly accompanied by two C-C and two C-N bond formation to produce 8-aryl-6H- chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-ones selectively. It also provides a straightforward route to natural product inspired pentacyclic pyrrolocoumarin derivatives from readily available building blocks.
引用
收藏
页数：4
相关论文
共 50 条
  • [1] Rhodium(III)-catalyzed intermolecular cascade annulation through C-H activation: Concise synthesis of rosettacin
    Song, Liangliang
    Tian, Guilong
    Van der Eyeken, Erik V.
    MOLECULAR CATALYSIS, 2018, 459 : 129 - 134
  • [2] Copper-Mediated Cascade C-H/N-H Annulation of Indolocarboxamides with Arynes: Construction of Tetracyclic Indoloquinoline Alkaloids
    Zhang, Ting-Yu
    Liu, Chang
    Chen, Chao
    Liu, Jian-Xin
    Xiang, Heng-Ye
    Jiang, Wei
    Ding, Tong-Mei
    Zhang, Shu-Yu
    ORGANIC LETTERS, 2018, 20 (01) : 220 - 223
  • [3] Triple C-H Activation/Annulation: In Situ Construction of Fluorescent Peptides
    Zhang, Zhefan
    Wan, Tianyan
    Quan, Qi
    Zang, Yiqi
    Xu, Jinyuan
    Tang, Shuo
    Wang, Nanxi
    Cai, Lingchao
    Song, Liangliang
    ORGANIC LETTERS, 2024, 26 (50) : 10915 - 10920
  • [4] Construction of Highly Functionalized Xanthones via Rh-Catalyzed Cascade C-H Activation/O-Annulation
    Nale, Sagar D.
    Maiti, Debabrata
    Lee, Yong Rok
    ORGANIC LETTERS, 2021, 23 (07) : 2465 - 2470
  • [5] Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens
    Khandelia, Tamanna
    Ghosh, Subhendu
    Panigrahi, Pritishree
    Shome, Rajib
    Ghosh, Siddhartha Sankar
    Patel, Bhisma K.
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16948 - 16964
  • [6] Oxidative C-H/C-H Annulation of Imidazopyridines and Indazoles through Rhodium-Catalyzed Vinylene Transfer
    Ghosh, Koushik
    Nishii, Yuji
    Miura, Masahiro
    ORGANIC LETTERS, 2020, 22 (09) : 3547 - 3550
  • [7] Intramolecular cascade annulation triggered by C-H activation via rhodium hydride intermediate
    Song, Liangliang
    Zhang, Xiaoyong
    Tian, Guilong
    Robeyns, Koen
    Van Meervelt, Luc
    Harvey, Jeremy N.
    Van der Eycken, Erik V.
    MOLECULAR CATALYSIS, 2019, 463 : 30 - 36
  • [8] Ruthenium(II)-catalyzed C-H alkenylation/annulation cascade for the rapid synthesis of benzoimidazoisoindoles
    Selvaraju, Manikandan
    Wang, Ying-Lien
    Sun, Chung-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1358 - 1362
  • [9] Access to 4-substituted isothiazoles through three-component cascade annulation and their application in C-H activation
    Huang, Guoling
    Li, Jian
    Ji, Xiaoliang
    Chen, Lu
    Liu, Qiang
    Chen, Xiuwen
    Huang, Yubing
    Li, Yibiao
    CHEMICAL COMMUNICATIONS, 2020, 56 (43) : 5763 - 5766
  • [10] Regioselective cascade annulation of indoles with alkynediones for construction of functionalized tetrahydrocarbazoles triggered by Cp*RhIII-catalyzed C-H activation
    Tang, Jiaxu
    Tang, Yuhai
    Wang, Xiaonan
    Wang, Yongzhuang
    Huang, Xiaoli
    Xu, Silong
    Li, Yang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (14): : 3809 - 3814
12345