Visible-Light-Promoted [3+2] Cycloaddition of 2H-Azirines with Quinones: Access to Substituted Benzo[f]isoindole-4,9-diones

被引：15
作者：
Wang, Lijia [1 ]
Liu, Chuang [1 ]
Li, Lei [1 ]
Wang, Xin [1 ]
Sun, Ran [1 ]
Zhou, Ming-Dong [1 ]
Wang, He [1 ]
机构：
[1] Liaoning Petrochem Univ, Sch Petrochem Engn, Fushun 113001, Liaoning, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 06期
基金：
中国国家自然科学基金;
关键词：
Photocatalysis; Cycloaddition; Quinones; 2H-Azirines; Benzo[f]isoindole-4; 9-diones; 1,3-DIPOLAR CYCLOADDITION; AROMATIZATION SEQUENCE; PHOTOREDOX CATALYSIS; CHEMISTRY; PYRIDINES; 3-PHENYL-2H-AZIRINES; CYCLIZATION; PYRAZINES; CLEAVAGE;
D O I：
10.1002/cjoc.202100728
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Comprehensive Summary A visible-light-promoteded [3 + 2] cycloaddition reaction of 2H-azirines with quinones has been developed under mild reaction conditions. The reaction provides a general and efficient strategy for the synthesis of the benzo[f]isoindole-4,9-diones scaffold via a tandem [3 + 2] cyclization/oxidative aromatization with molecular oxygen. Furthermore, preliminary studies for photocatalytic properties show that the benzo[f]isoindole-4,9-diones 3 can be used as photocatalysts in several organic transformations.
引用
收藏
页码：719 / 724
页数：6
相关论文
共 37 条
  • [31] A palladium-catalyzed cascade approach for the synthesis of 3,3a,4,6,7,8,9,9a-octahydro-1H-benzo[f]isoindole-1,5(2H)-diones
    Cheng, Dong
    Meng, Xiangzhen
    Wang, Dan
    Zhao, Xuan
    Wang, Yusheng
    Ji, Zhiyu
    JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (11-12) : 1107 - 1113
  • [32] Cascade Functionalization of C(sp3)-Br/C(sp2)-H Bonds: Access to Fused Benzo[e]isoindole-1,3,5-trione via Visible-Light-Induced Reductive Radical Relay Strategy
    Zhu, Jia-Nan
    Wang, Wen-Kang
    Zhu, Yuan
    Hu, Yin-Qiu
    Zhao, Sheng-Yin
    ORGANIC LETTERS, 2019, 21 (16) : 6270 - 6274
  • [33] Synthesis of E-3-Alkenyl 2H-Indazoles via Pd/Cu-Catalyzed Cross-coupling/Cyclization of 2-Iodoazoarenes with Terminal Allylenes and Visible-Light-Promoted Isomerization
    Mei, Kuan
    Huang, Rui
    Huang, Haiyang
    Bao, Hongli
    ACS CATALYSIS, 2024, 14 (24): : 18765 - 18773
  • [34] Visible light-promoted synthesis of 4-(sulfonylmethyl)isoquinoline-1,3(2H, 4H)-diones via a tandem radical cyclization and sulfonylation reaction
    Liu, Xu
    Cong, Tiantian
    Liu, Ping
    Sun, Peipei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (39) : 9416 - 9422
  • [35] An efficient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide
    Prajapti, Santosh Kumar
    Nagarsenkar, Atulya
    Babu, Bathini Nagendra
    TETRAHEDRON LETTERS, 2014, 55 (24) : 3507 - 3510
  • [36] Visible-light-enabled aerobic oxidative Csp3-H functionalization of glycine derivatives using an organic photocatalyst: access to substituted quinoline-2-carboxylates
    Wang, Jingxin
    Li, Liqi
    Guo, Ying
    Li, Shengyu
    Wang, Shutao
    Li, Ying
    Zhang, Yuan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (40) : 8179 - 8185
  • [37] Lewis Acidic Ionic-Liquid-Catalyzed Radical-Cascade Alkylation/Cyclization of N-Alkyl-N-methacryloyl Benzamides with Alkanes via Visible-Light-Induced Ligand-to-Metal Charge Transfer: Access to Alkylated Isoquinoline-1,3(2H,4H)-diones
    Zhang, Tao
    Ren, Xinxin
    Li, Jingkun
    Wang, Yanhong
    Wang, Bin
    Chen, Ziren
    Xia, Yu
    Wu, Shaofeng
    Liu, Chenjiang
    Zhang, Yonghong
    ORGANIC LETTERS, 2024, 26 (48) : 10259 - 10266
1234