CuI-Catalyzed Selenylation of Pyrrolo[2,1-a]isoquinolines and Other Electron-Rich Heteroarenes

被引:0
|
作者
Zhou, Jing [1 ]
Han, Jia-Yi [1 ]
Yu, Xin [1 ]
Yang, Liu [1 ]
Jiang, Man [1 ]
Li, Yun-Meng [1 ]
Cui, Hai-Lei [1 ]
机构
[1] Chongqing Univ Arts & Sci, Coll Chem & Environm Engn, Lab Asymmetr Synth, Chongqing 402160, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期
基金
中国国家自然科学基金;
关键词
METAL-FREE SYNTHESIS; N-PHENYLSELENOPHTHALIMIDE; ORGANOSELENIUM CHEMISTRY; CYCLIZATION; ALKALOIDS; SELENIUM; DISULFIDES; OXIDATION; INDOLES; REAGENT;
D O I
10.1021/acs.joc.4c01462
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have established a mild CuI-catalyzed selenylation of pyrrolo[2,1-a]isoquinoline derivatives in the presence of mCPBA (m-chloroperoxybenzoic acid) at ambient temperature. Corresponding organoselenides have been prepared readily in 53-92% yields. This process can also be expanded to the modification of pyrroles, azaindole, and indoles, delivering the desired heterocyclic selenides in moderate to good yields.
引用
收藏
页码:14050 / 14060
页数:11
相关论文
共 50 条
  • [31] NHC-Mediated Synthesis of Pyrrolo[2,1-a]isoquinolines and Their Photophysical Investigations
    Krishnan, Jagadeesh
    Vedhanarayanan, Balaraman
    Sasidhar, B. S.
    Varughese, Sunil
    Nair, Vijay
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (06) : 623 - 627
  • [32] Copper-Catalyzed Cyclization/Oxidation/Aromatization Cascade: Efficient Synthesis of Trifluoromethylated Pyrrolo[2,1-a]isoquinolines
    Tao, Lili
    Xu, Zhiliang
    Han, Jing
    Deng, Hongmei
    Shao, Min
    Chen, Jie
    Zhang, Hui
    Cao, Weiguo
    SYNTHESIS-STUTTGART, 2016, 48 (23): : 4228 - 4236
  • [33] Synthesis of Pyrrolo[2,1-a]isoquinolines through Cu-Catalyzed Condensation/Addition/Oxidation/Cyclization Cascade
    Cui, Hai-Lei
    Chen, Xiao-Hui
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22): : 15435 - 15447
  • [34] Synthesis of pyrrolo[2,1-a]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline
    Yavari, Issa
    Piltan, Mohammad
    Moradi, Loghman
    TETRAHEDRON, 2009, 65 (10) : 2067 - 2071
  • [35] Ring annulation with tetrahydroisoquinoline-derived enaminones:: Highly convergent routes to functionalized pyrrolo[2,1-a]- and indolo[2,1-a]isoquinolines
    Barun, O
    Chakrabarti, S
    Ila, H
    Junjappa, H
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12): : 4457 - 4461
  • [36] HI/DMSO-Based Chemoselective Oxidative Halogenation of Pyrrolo[2,1-a ]isoquinolines
    Cui, Hai-Lei
    SYNLETT, 2025,
  • [37] CuI-catalyzed synthesis of (benzo)imidazo[2,1-a]isoquinolinone derivatives via successive α-arylation, deacylation and benzyl automatic oxidation
    Miao, Wei-Qing
    Liu, Jian-Quan
    Wang, Xiang-Shan
    TETRAHEDRON, 2020, 76 (21)
  • [38] Assembly of isoquinolines via CuI-catalyzed coupling of β-keto esters and 2-halobenzylamines
    Wang, Bao
    Lu, Biao
    Jiang, Yongwen
    Zhang, Yihua
    Ma, Dawei
    ORGANIC LETTERS, 2008, 10 (13) : 2761 - 2763
  • [39] Iron-catalyzed oxidative [3+2] cycloaddition-aromatization cascade: Synthesis of pyrrolo-[2,1-a]isoquinolines
    Hu, Wen Jing
    Liu, Na Na
    Wusiman, Abudureheman
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (09) : 1633 - 1640
  • [40] POCl3/Sulfoxide and AcCl/Sulfoxide Mediated Chlorination of Pyrrolo[2,1-a]isoquinolines
    Cui, Hai-Lei
    Chen, Xiao-Hui
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11935 - 11944