Iron-Catalyzed Synthesis of Peroxylpyrrolo[2,1-a]isoquinolines through Oxidative Dearomatization

被引:4
作者
Huang, Xiang [1 ,2 ]
Yu, An-Ni [1 ]
Yang, De [1 ]
Gao, Xin [1 ]
Liang, Shu-Ting [1 ]
Pei, Shu-Chen [2 ]
Cui, Hai-Lei [1 ]
机构
[1] Chongqing Univ Arts & Sci, Coll Chem & Environm Engn, Chongqing 402160, Peoples R China
[2] Chongqing Univ Sci & Technol, Sch Chem & Chem Engn, Chongqing 401331, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE PEROXIDATION; ARTEMISININ; ALKALOIDS; QINGHAOSU;
D O I
10.1021/acs.joc.3c01824
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild late-stage modification of pyrrolo-[2,1-a]-isoquinolines was established through iron-catalyzed oxidative dearomatization and peroxidation. Peroxylated pyrroloisoquinolines have been prepared readily with hydroperoxide in low to good yields (up to 72%) at room temperature. Interestingly, the treatment of fully aromatized pyrrolo-[1,2-a]-quinolines under the current reaction system resulted in the formation of ring-opening products.
引用
收藏
页码:15326 / 15334
页数:9
相关论文
共 61 条
  • [1] METABOLITIES OF THE MARINE PROSOBRANCH MOLLUSK LAMELLARIA SP
    ANDERSEN, RJ
    FAULKNER, DJ
    HE, CH
    VANDUYNE, GD
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) : 5492 - 5495
  • [2] Anticancer Properties of Lamellarins
    Bailly, Christian
    [J]. MARINE DRUGS, 2015, 13 (03) : 1105 - 1123
  • [3] Banwell MG, 2020, TARG HETEROCYCL SYST, V24, P208, DOI 10.17374/targets.2021.24.208
  • [4] Iron Catalysis in Organic Synthesis
    Bauer, Ingmar
    Knoelker, Hans-Joachim
    [J]. CHEMICAL REVIEWS, 2015, 115 (09) : 3170 - 3387
  • [5] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254
  • [6] PEROXY NATURAL-PRODUCTS
    CASTEEL, DA
    [J]. NATURAL PRODUCT REPORTS, 1992, 9 (04) : 289 - 312
  • [7] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules
    Cernak, Tim
    Dykstra, Kevin D.
    Tyagarajan, Sriram
    Vachal, Petr
    Krska, Shane W.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) : 546 - 576
  • [8] Iron- and Indium-Catalyzed Reactions toward Nitrogen- and Oxygen-Containing Saturated Heterocycles
    Cornil, Johan
    Gonnard, Laurine
    Bensoussan, Charlelie
    Serra-Muns, Anna
    Gnamm, Christian
    Commandeur, Claude
    Commandeur, Malgorzata
    Reymond, Sebastien
    Guerinot, Amandine
    Cossy, Janine
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (03) : 761 - 773
  • [9] Cui H.-L., 2022, TARGETS HETEROCYCLIC, V26, P222
  • [10] Bromination of Pyrrolo[2,1-a]isoquinolines with Acetyl Bromide and Dimethyl Sulfoxide
    Cui, Hai-Lei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05) : 2822 - 2831