Palladium-Catalyzed Formal (5+6) Cycloaddition of Vinylethylene Carbonates with Isatoic Anhydrides for the Synthesis of MediumSized N,O-Containing Heterocycles

被引:17
作者
Wu, Hui-Hui [1 ]
Fan, Xiao-Zu [1 ]
Tang, Zhe [1 ]
Zhang, Heng [1 ]
Cai, Lu-Yu [1 ]
Bi, Xiao-Fan [1 ]
Zhao, Hong-Wu [1 ]
机构
[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
关键词
DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; RING-EXPANSION; CONSTRUCTION; ACCESS; REARRANGEMENT;
D O I
10.1021/acs.orglett.1c00729
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under the reaction conditions of Pd(PPh3)(4) (2.5 mol %) and PPh3 (10 mol %) in EtOAc at 60 degrees C, the formal (5 + 6) cycloaddition of vinylethylene carbonates with isatoic anhydrides proceeded smoothly and furnished medium-sized N,O-containing heterocycles in reasonable chemical yields. The chemical structures of the title products were clearly identified by X-ray diffraction analysis.
引用
收藏
页码:2802 / 2806
页数:5
相关论文
共 45 条
  • [1] Nickel-Catalyzed Synthesis of Quinazolinediones
    Beutner, Gregory L.
    Hsiao, Yi
    Razler, Thomas
    Simmons, Eric M.
    Wertjes, William
    [J]. ORGANIC LETTERS, 2017, 19 (05) : 1052 - 1055
  • [2] Medium-Sized-Ring Analogues of Dibenzodiazepines by a Conformationally Induced Smiles Ring Expansion
    Costil, Romain
    Lefebvre, Quentin
    Clayden, Jonathan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (46) : 14602 - 14606
  • [3] 1,3-Dipolar Cycloaddition-Decarboxylation Reactions of an Azomethine Ylide with Isatoic Anhydrides: Formation of Novel Benzodiazepinones
    D'Souza, Asha M.
    Spiccia, Nadia
    Basutto, Jose
    Jokisz, Pawel
    Wong, Leon S. -M.
    Meyer, Adam G.
    Holmes, Andrew B.
    White, Jonathan M.
    Ryan, John H.
    [J]. ORGANIC LETTERS, 2011, 13 (03) : 486 - 489
  • [4] Palladium-catalysed cyclisation of vinylethylene carbonates and anhydrides: a new approach to diverse medium-sized bislactones
    Dai, Qing-Song
    Tao, Ying-Mao
    Zhang, Xiang
    Leng, Hai-Jun
    Huang, Hua
    Xiang, Peng
    Li, Qing-Zhu
    Wang, Qi-Wei
    Li, Jun-Long
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (82) : 12439 - 12442
  • [5] Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis
    Das, Pulakesh
    Gondo, Satoshi
    Nagender, Punna
    Uno, Hiroto
    Tokunaga, Etsuko
    Shibata, Norio
    [J]. CHEMICAL SCIENCE, 2018, 9 (13) : 3276 - 3281
  • [6] Electron-Deficient Alkynes as Dipolarophile in Pd-Catalyzed Enantioselective (3+2) Cycloaddition Reaction with Vinyl Cyclopropanes
    Ding, Wen-Ping
    Zhang, Gao-Peng
    Jiang, Yang-Jie
    Du, Juan
    Liu, Xiu-Yan
    Chen, Di
    Ding, Chang-Hua
    Deng, Qing-Hai
    Hou, Xue-Long
    [J]. ORGANIC LETTERS, 2019, 21 (17) : 6805 - 6810
  • [7] Palladium-Catalyzed Asymmetric Decarboxylative [4+2] Dipolar Cycloaddition of 4-Vinyl-1,3-dioxan-2-ones with α,β-Disubstituted Nitroalkenes Enabled by a Benzylic Substituted P,N-Ligand
    Du, Juan
    Hua, Yuan-Da
    Jiang, Yang-Jie
    Huang, Shuai
    Chen, Di
    Ding, Chang-Hua
    Hou, Xue-Long
    [J]. ORGANIC LETTERS, 2020, 22 (14) : 5375 - 5379
  • [8] Tuning Vinylethylene Carbonates into [4+2] Cycloaddition via Silylation and Vinylogous Peterson Elimination
    Feng, Wei
    Xu, Li
    Li, Deng-Yuan
    Liu, Pei-Nian
    [J]. ORGANIC LETTERS, 2020, 22 (13) : 5094 - 5098
  • [9] Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization
    Fu, Wei
    Wang, Lianhui
    Yang, Zi
    Shen, Jiang-Shan
    Tang, Fei
    Zhang, Jiayi
    Cui, Xiuling
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (06) : 960 - 963
  • [10] Palladium-Catalyzed [5+2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes
    Gao, Xing
    Zhu, Dongyu
    Chen, Yuehua
    Deng, Hao
    Jiang, Feng
    Wang, Wei
    Wu, Yongjun
    Guo, Hongchao
    [J]. ORGANIC LETTERS, 2020, 22 (18) : 7158 - 7163