Nitration of Pyrrolo[2,1-a]isoquinolines

被引:4
|
作者
Chen, Xiao-Hui [1 ]
Ma, Dan-Dan [1 ,2 ]
Gao, Xin [1 ]
Li, Yun-Meng [1 ]
Jiang, Da-Bo [1 ]
Ma, Chao [2 ]
Cui, Hai-Lei [1 ]
机构
[1] Chongqing Univ Arts & Sci, Chongqing 402160, Peoples R China
[2] Hubei Univ, Coll Chem & Chem Engn, Wuhan 430062, Hubei, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期
基金
中国国家自然科学基金;
关键词
C-H NITRATION; CERIUM(IV) AMMONIUM-NITRATE; BOND NITRATION; FUNCTIONALIZATION; ALKALOIDS; 8-AMINOQUINOLINES; LAMELLARINS; CONVERSION; INDOLINES; EFFICIENT;
D O I
10.1021/acs.joc.3c00125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have successfully modified a series of pyrrolo[2,1-a]isoquinolines via direct nitration under mild reaction conditions. Easily accessible nitrates including CAN, Cu(NO3)2 center dot H2O, and Fe(NO3)3 center dot 9H2O all can serve as effective nitrating reagents for functionalizing pyrrolo[2,1-a]isoquinolines. Various nitro-bearing pyrrolo[2,1-a]isoquinolines have been efficiently prepared in acceptable to good yields.
引用
收藏
页码:4649 / 4661
页数:13
相关论文
共 50 条
  • [31] 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
  • [32] Silver(I)-promoted oxidative cyclisation to pyrrolo[2,1-a]isoquinolines and application to the synthesis of (±)-crispine A
    Agarwal, Sameer
    Kataeva, Olga
    Schmidt, Ulrike
    Knoelker, Hans-Joachim
    RSC ADVANCES, 2013, 3 (04): : 1089 - 1096
  • [33] Synthesis of pyrrolo[2,1-a]isoquinolines by a tandem 1,5-electrocyclisation-oxidation process
    Toth, Judit
    Nedves, Andrea
    Dancso, Andras
    Blasko, Gabor
    Toke, Laszlo
    Nyerges, Miklos
    SYNTHESIS-STUTTGART, 2007, (07): : 1003 - 1014
  • [34] Modification of Pyrrolo[2,1-a]isoquinolines and Polysubstituted Pyrroles via Methylenation with Acetyl Chloride and Dimethylsulfoxide
    Li, Wan-Zhen
    Zhang, Wei
    Chen, Xiao-Hui
    Wang, Zhao-Dong
    Cui, Hai-Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17): : 11491 - 11502
  • [35] NH4OAc/DMSO-Promoted Benzylation of Pyrrolo[2,1-a]isoquinolines
    Chen, Xiao-Hui
    Lhazom, Tsesong
    Cui, Hai-Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 13598 - 13609
  • [36] REISSERT COMPOUND CHEMISTRY .5. FORMATION OF PYRROLO[1,2-A]-QUINOLINES AND PYRROLO[2,1-A]ISOQUINOLINES
    UFF, BC
    BUDHRAM, RS
    CONSTERDINE, MF
    HICKS, JK
    SLINGSBY, BP
    PEMBLINGTON, JA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (18): : 2018 - 2022
  • [37] Studies on the synthesis of benzimidazo [2,1-a] isoquinolines
    Deady, LW
    Loria, PM
    Rodemann, T
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (10) : 941 - 945
  • [38] A synthesis of pyrrolo[2,1-a]isoquinolines through the reaction of activated acetylenes and isoquinoline in the presence of ethyl bromopyruvate
    Yavari, Issa
    Hossaini, Zinatossadat
    Sabbaghan, Maryam
    TETRAHEDRON LETTERS, 2006, 47 (34) : 6037 - 6040
  • [39] Controllable Diastereodivergent Synthesis of Pyrrolo[2,1-a]isoquinolines via Catalytic Intramolecular Acylsulfenylation of Activated Alkenes
    Liu, Wei
    Du, Shan-Tao
    Wang, Shu-Yue
    Liao, Wei-Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09): : 4829 - 4839
  • [40] CuI-Catalyzed Selenylation of Pyrrolo[2,1-a]isoquinolines and Other Electron-Rich Heteroarenes
    Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Ave., Chongqing, Yongchuan
    402160, China
    J. Org. Chem., 2024, 19 (14050-14060):