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
  • [41] 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
  • [42] Transformable Sulfoximine Assisted One-Pot Double Annulation of Vinylic C-H Bonds with Unactivated Alkynes
    Shankar, Majji
    Guntreddi, Tirumaleswararao
    Ramesh, E.
    Sahoo, Akhila K.
    ORGANIC LETTERS, 2017, 19 (20) : 5665 - 5668
  • [43] Rhodium-Catalyzed C-H Activation/Annulation Cascade of Aryl Oximes and Propargyl Alcohols to Isoquinoline N-Oxides
    Li, Yuan
    Fang, Feifei
    Zhou, Jianhui
    Li, Jiyuan
    Wang, Run
    Liu, Hong
    Zhou, Yu
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (13) : 3305 - 3310
  • [44] Rhodium-Catalyzed Enantioselective Oxidative [3+2] Annulation of Arenes and Azabicyclic Olefins through Twofold C-H Activation
    Mi, Ruijie
    Zheng, Guangfan
    Qi, Zisong
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (49) : 17666 - 17670
  • [45] Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones
    Fang, Taibei
    Zhang, Shiwen
    Ye, Qingqing
    Kong, Shuwen
    Yang, Tingting
    Tang, Kaijie
    He, Xinwei
    Shang, Yongjia
    MOLECULES, 2022, 27 (23):
  • [46] Synthesis of Polysubstituted Phenols by Rhodium-Catalyzed C-H/Diazo Coupling and Tandem Annulation
    Liu, Min
    Yan, Kelu
    Wen, Jiangwei
    Li, Xue
    Wang, Xiaoyu
    Lu, Fengjie
    Wang, Xiu
    Wang, Hua
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (07) : 1855 - 1860
  • [47] Rhodium(III)-N-Heterocyclic Carbene-Driven Cascade C-H Activation Catalysis
    Ghorai, Debasish
    Choudhury, Joyanta
    ACS CATALYSIS, 2015, 5 (04): : 2692 - 2696
  • [48] Rhodium(III)-catalyzed annulation of 2-arylimidazo[1,2-a]pyridines and alkynes via direct double C-H activation
    Wang, Wei
    Niu, Jun-Long
    Liu, Wen-Bo
    Shi, Tan-Hao
    Hao, Xin-Qi
    Song, Mao-Ping
    TETRAHEDRON, 2015, 71 (42) : 8200 - 8207
  • [49] Synthesis of Phenalenyl-Fused Pyrylium Cations: Divergent C-H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes
    Yin, Jiangliang
    Tan, Meiling
    Wu, Di
    Jiang, Ruyong
    Li, Chengming
    You, Jingsong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13094 - 13098
  • [50] Synthesis and Application of Heterocyclic Germatranes via Rhodium-Catalyzed Directed C-H Activation/Annulation with Alkynyl Germatranes and Palladium-Catalyzed Cross-Coupling
    Xu, Meng-Yu
    Wang, Chao
    Jiang, Wei-Tao
    Xiao, Bin
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (08) : 1706 - 1711
12345