Visible-light-induced acylation/cyclization of active alkenes: facile access to acylated isoquinolinones

被引：10
作者：
Guo, Yang [1 ]
Huang, Peng-Fei [1 ]
Liu, Yu [1 ]
He, Bin-Hong [1 ]
机构：
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 18期
基金：
中国国家自然科学基金;
关键词：
CARBOXYLIC-ACIDS; RADICAL CYCLIZATION; CATALYZED SYNTHESIS; SYNTHETIC METHODS; H ANNULATION; CASCADE; METAL; ALKALOIDS; CHLORIDES; INDOLES;
D O I：
10.1039/d2ob00528j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nitrogen heterocycles, especially polycyclic compounds, are significant skeletons in valuable molecules. Herein, we developed an efficient and practical visible-light-induced acylation/cyclization of active alkenes with acyl oxime derivatives for constructing acylated indolo/benzimidazo-[2,1,a]isoquinolin-6(5H) ones. This reaction was compatible with various functional groups and a series of fused indole/imidazole skeletons were prepared in up to 95% yield at room temperature.
引用
收藏
页码：3767 / 3778
页数：12
相关论文
共 95 条
  • [1] Divergent C-H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles
    Alam, Khyarul
    Hong, Sung Won
    Oh, Kyung Hwan
    Park, Jin Kyoon
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13387 - 13391
  • [2] Acyl Radical Chemistry via Visible-Light Photoredox Catalysis
    Banerjee, Arghya
    Lei, Zhen
    Ngai, Ming-Yu
    [J]. SYNTHESIS-STUTTGART, 2019, 51 (02): : 303 - 333
  • [3] Metal-free oxidative acylation/cyclization of N-methacryloyl-2-phenylbenzoimidazole with aryl aldehydes: an easy access to benzimidazo[2,1-a]isoquinolin-6(5H)-ones
    Boora, Ramesh
    Kumar, G. Ravi
    Reddy, B. V. Subba
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (44) : 9627 - 9630
  • [4] A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction
    Bressy, C
    Alberico, D
    Lautens, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) : 13148 - 13149
  • [5] Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1-a]-Isoquinolines via Rh(III)-Catalyzed C-H Functionalizations of 2-Arylindoles with Sulfoxonium Ylides
    Chen, Guang
    Zhang, Xinying
    Jia, Ruixue
    Li, Bin
    Fan, Xuesen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (19) : 3781 - 3787
  • [6] A Three-Component Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and 1-(Prop-2-yn-1-yl)indoles under Catalyst-Free Conditions
    Chen, Huajun
    Liu, Mengli
    Qiu, Guanyinsheng
    Wu, Jie
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) : 146 - 150
  • [7] Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions
    Chen, Jian-Qiang
    Tu, Xiaodong
    Qin, Binyan
    Huang, Shaoxin
    Zhang, Jun
    Wu, Jie
    [J]. ORGANIC LETTERS, 2022, 24 (02) : 642 - 647
  • [8] Visible-Light-Mediated Nitrogen-Centered Radical Strategy: Preparation of 3-Acylated Spiro[4,5]trienones
    Chen, Pu
    Xie, Jun
    Chen, Zan
    Xiong, Bi-Quan
    Liu, Yu
    Yang, Chang-An
    Tang, Ke-Wen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (18) : 4440 - 4446
  • [9] Nickel-Catalyzed Arylcarbamoylation of Alkenes of N-(o-lodoaryl)acrylamides with Nitroarenes via Reductive Aminocarbonylation: Facile Synthesis of Carbamoyl-Substituted Oxindoles
    Cheng, Chaozhihui
    Xiang, Jian-Nan
    Zhu, Yan-Ping
    Peng, Zhi-Hong
    Li, Jin-Heng
    [J]. ORGANIC LETTERS, 2021, 23 (24) : 9543 - 9547
  • [10] Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis
    Cheng, Yuan-Yuan
    Yu, Ji-Xin
    Lei, Tao
    Hou, Hong-Yu
    Chen, Bin
    Tung, Chen-Ho
    Wu, Li-Zhu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (51) : 26822 - 26828
12345678910