Iron Catalyzed [3+2] Cycloaddition of Tetrahydroisoquinoline: Synthesis of Dihydropyrrolo[2,1-a]isoquinolines

被引：12
|
作者：
Liu, Si-Wei [1 ,2 ]
Ma, Dan-Dan [1 ]
Zhu, Xin-Xin [1 ]
Luo, Cheng-Dan [1 ]
Tan, Hui-Lin [1 ]
Ju, Xiao-Li [1 ]
Tan, Xue [1 ]
Tang, Xiao-Hui [1 ]
Huang, Jie [1 ]
Wang, Jia [1 ]
Wang, Xian-Xun [2 ]
Cui, Hai-Lei [1 ]
机构：
[1] Chongqing Univ Arts & Sci, Lab Asymmetr Synth, 319 Honghe Ave, Chongqing 402160, Peoples R China
[2] Tonichem Pharmaceut Technol Co Ltd, Huizhou 516008, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 9卷 / 10期
基金：
中国国家自然科学基金;
关键词：
Iron chloride; Dihydropyrrolo[2; 1-a]isoquinoline; Tetrahydroisoquinoline; Cycloaddition; Morita-Baylis-Hillman carbonate; BAYLIS-HILLMAN REACTION; EFFICIENT APPROACH; AZOMETHINE YLIDES; LAMELLARIN CORE; DERIVATIVES; CASCADE; CYCLIZATION; TANDEM; ANNULATION; REACTIVITY;
D O I：
10.1002/ajoc.202000211
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed an iron(III) chloride hexahydrate catalyzed formal [3+2] cycloaddition of tetrahydroisoquinolines with amide group-bearing Morita-Baylis-Hillman (MBH) carbonates. A range of highly functionalized dihydropyrrolo[2,1-a]isoquinolines could be prepared through SN2'/oxidation/electrocyclization/aromatization cascade (32-62% yield).
引用
收藏
页码：1617 / 1622
页数：6
相关论文
共 50 条
  • [41] Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1-a]-Isoquinolines via Rh(III)-Catalyzed C-H Functionalizations of 2-Arylindoles with Sulfoxonium Ylides
    Chen, Guang
    Zhang, Xinying
    Jia, Ruixue
    Li, Bin
    Fan, Xuesen
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (19) : 3781 - 3787
  • [42] Synthesis of imidazo and benzimidazo[2,1-a]isoquinolines by rhodium-catalyzed intramolecular double C-H bond activation
    Reddy, Vutukuri Prakash
    Iwasaki, Takanori
    Kambe, Nobuaki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (14) : 2249 - 2253
  • [43] Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a ]isoquinolines Bearing Indeno[1,2-b ]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction
    Moghaddam, Firouz Matloubi
    Moafi, Atiyeh
    Jafari, Behzad
    Vilinger, Alexander
    Langer, Peter
    SYNLETT, 2020, 31 (03) : 267 - 271
  • [44] Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3+2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions
    Ma, Xiaoming
    Meng, Suzhi
    Zhang, Xiaofeng
    Zhang, Qiang
    Yan, Shenghu
    Zhang, Yue
    Zhang, Wei
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1225 - 1233
  • [45] 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
  • [46] Diastereoselective construction of pyrrolo[2,1-a]isoquinoline-based bispirooxindoles through a three-component [3+2] cycloaddition
    Guo, Jiaomei
    Zhao, Yang
    Fang, Dongmei
    Wang, Qilin
    Bu, Zhanwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (33) : 6025 - 6034
  • [47] Intramolecular Copper-Catalyzed Asymmetric Propargylic [4+2]-Cycloaddition toward Optically Active Tetrahydroisoindolo[2,1-a]quinoxalines
    Li, Ling
    Chen, Xiu-Shuai
    Hu, Xiang-Ping
    ORGANIC LETTERS, 2022, 24 (29) : 5433 - 5438
  • [48] Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions
    Chen, Jian-Qiang
    Tu, Xiaodong
    Qin, Binyan
    Huang, Shaoxin
    Zhang, Jun
    Wu, Jie
    ORGANIC LETTERS, 2022, 24 (02) : 642 - 647
  • [49] Radical Cyclizations of N-Methylallyl-2-arylindoles with Polychloromethanes to Assemble Polychloroalkylated Indolo[2,1-a]isoquinolines
    Pan, Mei
    Liao, Hailin
    Liu, Jiyao
    Gao, Lijiu
    Liu, Yun
    Liu, Xiaoqin
    Rong, Liangce
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [50] Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity
    Reyes-Gutierrez, Paul E.
    Camacho, Jose R.
    Teresa Ramirez-Apan, Ma.
    Osornio, Yazmin M.
    Martinez, Roberto
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (19) : 4374 - 4382
12345