Derivation of Benzothiadiazine-1,1-dioxide Scaffolds via Transition Metal-Catalyzed C-H Activation/Annulation

被引:6
|
作者
Lai, Ruizhi [1 ,2 ]
Xu, Shuran [1 ,2 ]
Zhang, Qingyao [1 ,2 ]
Zhou, Hui [1 ,2 ]
Luo, Cankun [1 ,2 ]
Wang, Yuerong [1 ,2 ]
Hai, Li [1 ,2 ]
Wu, Yong [1 ,2 ]
机构
[1] Sichuan Univ, Sichuan Engn Lab Plant Sourced Drug, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst,Educ M, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, Chengdu 610041, Sichuan, Peoples R China
来源
CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 16期
关键词
C-H activation; Annulation; Ruthenium; Rhodium; Heterocycles; Fused-ring systems; Spiro compounds; Diazo compounds; CONSTRUCTION; 1,1-DIOXIDES; STRATEGY; TANDEM;
D O I
10.1002/cjoc.202300095
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Comprehensive SummaryBenzothiadiazine-1,1-dioxide scaffold is bioactive framework with wild utility and applications. Synthesis of benzothiadiazine-fused isoquinoline derivatives and spiro benzothiadiazine derivatives through transition metal-catalyzed C-H activation/annulation was reported. 3-Phenyl-2H-benzothiadiazine-1,1-dioxide was used as the reaction substrate, and vinylene carbonate and 4-diazopyrazolone were used as the coupling reagents, respectively. This strategy provides straightforward access to complex N-heterocycles in a highly efficient and simple manner.
引用
收藏
页码:1973 / 1978
页数:6
相关论文
共 50 条
  • [1] Transition metal-catalyzed C-H functionalization of arylacetic acids for the synthesis of benzothiadiazine 1,1-dioxides
    Patil, Bhausaheb N.
    Lade, Jatin J.
    Karpe, Aniket S.
    Pownthurai, B.
    Vadagaonkar, Kamlesh S.
    Mohanasrinivasan, V.
    Chaskar, Atul C.
    TETRAHEDRON LETTERS, 2019, 60 (13) : 891 - 894
  • [2] Transition Metal-Catalyzed C-H Activation of Indoles
    Sandtorv, Alexander H.
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) : 2403 - 2435
  • [3] Advances in the Synthesis of Fluorinated Scaffolds by Transition Metal-Catalyzed C-H Bond Activation
    Mazeh, Sara
    Lapuh, Maria Ivana
    Besset, Tatiana
    CHIMIA, 2020, 74 (11) : 871 - 877
  • [4] Vinylene Carbonate as Synthon in Transition Metal-Catalyzed C-H Bond Activation/Annulation Reactions
    Cui, Xiaofan
    Chauvin, Remi
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (20) : 3400 - 3412
  • [5] Transition Metal-Catalyzed Intermolecular Cascade C-H Activation/Annulation Processes for the Synthesis of Polycycles
    Song, Liangliang
    Van der Eycken, Erik V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (01) : 121 - 144
  • [6] Transition Metal-Catalyzed Dual C-H Activation/Annulation Reactions Involving Internal Alkynes
    Doraghi, Fatemeh
    Karimtabar, Mohammad Sadegh
    Ghasemi, Mehran
    Larijani, Bagher
    Mahdavi, Mohammad
    CHEMICAL RECORD, 2024, 24 (07):
  • [7] Transition metal-catalyzed borylation of alkanes and arenes via C-H activation
    Ishiyama, T
    Miyaura, N
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 680 (1-2) : 3 - 11
  • [8] Reaction exploration for transition metal-catalyzed C-H activation
    Dewyer, Amanda
    Zimmerman, Paul
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [9] Synthesis of functionalized benzothiadiazine 1,1-dioxide derivatives via intramolecular C-H activation reactions of trichloroacetamidine and benzenesulfonyl chloride
    Nematpour, Manijeh
    Rezaee, Elham
    Jahani, Mehdi
    Tabatabai, Sayyed Abbas
    TETRAHEDRON LETTERS, 2018, 59 (21) : 2054 - 2056
  • [10] Transition metal-catalyzed olefin arylation via C-H bond activation of arenes
    Matsumoto, Takaya
    CATALYSIS SURVEYS FROM ASIA, 2007, 11 (1-2) : 31 - 48