Visible-Light-Mediated Intermolecular [2+2]-Cycloaddition Reaction of 3-Alkylideneindolin-2-one with Alkenes via Triplet Energy Transfer for the Synthesis of 3-Spirocyclobutyl Oxindoles

被引:8
|
作者
Shi, Shao-Xian [1 ]
Zhang, Huan-Huan [1 ]
Wang, Yi-Lin [1 ]
Jiang, Lin-Hong [1 ]
Xu, Peng-Fei [1 ,2 ]
Luo, Yong-Chun [1 ,2 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chinese Acad Agr Sci, Lanzhou Vet Res Inst, State Key Lab Vet Etiol Biol, Lanzhou 730000, Peoples R China
关键词
WELWITINDOLINONE;
D O I
10.1021/acs.orglett.3c01695
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[2 + 2]-Cycloaddition is the most straightforward approachto theconstruction of cyclobutanes. In this paper, the intermolecular [2+ 2]-cycloaddition reaction of 3-alkylideneindolin-2-ones with alkeneswas achieved. This reaction can be used in the synthesis of 3-spirocyclobutyloxindoles, polycyclic oxindoles, and late stage modification of somedrug molecules.
引用
收藏
页码:5426 / 5430
页数:5
相关论文
共 50 条
  • [1] Synthesis of azetidines via visible-light-mediated intermolecular [2+2] photocycloadditions
    Marc R. Becker
    Emily R. Wearing
    Corinna S. Schindler
    Nature Chemistry, 2020, 12 : 898 - 905
  • [2] Synthesis of azetidines via visible-light-mediated intermolecular [2+2] photocycloadditions
    Becker, Marc R.
    Wearing, Emily R.
    Schindler, Corinna S.
    NATURE CHEMISTRY, 2020, 12 (10) : 898 - +
  • [3] Visible-Light-Mediated Heterocycle Functionalization via Geometrically Interrupted [2+2] Cycloaddition
    Popescu, Mihai V.
    Mekereeya, Aroonroj
    Alegre-Requena, Juan V.
    Paton, Robert S.
    Smith, Martin D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (51) : 23020 - 23024
  • [4] Visible light induced intermolecular [2+2]-cycloaddition reactions of 3-ylideneoxindoles through energy transfer pathway
    Zou, You-Quan
    Duan, Shu-Wen
    Meng, Xiang-Gao
    Hu, Xiao-Qiang
    Gao, Shuang
    Chen, Jia-Rong
    Xiao, Wen-Jing
    TETRAHEDRON, 2012, 68 (34) : 6914 - 6919
  • [5] Synthesis of Bishomocubanone Derivatives via Visible-Light-Induced Intramolecular [2+2] Cycloaddition Reaction
    Yan, Bingning
    Zhang, Qingzhong
    Ling, Yifei
    Liu, Jiaxin
    Yang, Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [6] An Efficient Synthesis of Naphtho[2,3-b]furan-4,9-diones via Visible-Light-Mediated [3+2] Cycloaddition Reaction
    Tan, Hongbo
    Qi, Zehui
    Yu, Yuanhui
    Zhang, Xu
    Xiang, Yuheng
    Huang, Jingwen
    Xu, Zhigang
    Tang, Dianyong
    Chen, Zhongzhu
    Wang, Bochu
    MOLECULES, 2023, 28 (12):
  • [7] Metal-free visible-light-promoted intermolecular [2+2]-cycloaddition of 3-ylideneoxindoles
    Wu, Ling-Ling
    Yang, Gao H.
    Guan, Zhi
    He, Yan-Hong
    TETRAHEDRON, 2017, 73 (14) : 1854 - 1860
  • [8] Energy Transfer Catalysis by Visible Light: Atrop- and Regio-Selective Intermolecular [2+2]-Photocycloaddition of Maleimide with Alkenes
    Ahuja, Sapna
    Jockusch, Steffen
    Ugrinov, Angel
    Sivaguru, Jayaraman
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1478 - 1481
  • [9] Synthesis of 3-alkylseleno-2-cylcobutenone via [2+2] cycloaddition reaction of alkyneselenolate with diphenylketene
    Koketsu, M
    Kanoh, M
    Ishihara, H
    SYNLETT, 2002, (05) : 805 - 807
  • [10] Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
    Tan, Hong-Bo
    Zhou, Jia-Ying
    Liu, Ying-Shan
    Lei, Tong
    Wang, Shi-Yu
    Hu, Shuang-Shuang
    Zhang, Xu
    Xu, Zhi-Gang
    Tang, Dian-Yong
    Chen, Zhong-Zhu
    Wang, Bo-Chu
    MOLECULES, 2023, 28 (22):