Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-a]isoquinolines

被引：30
作者：
Yang, Ziqi [1 ]
Lu, Ning [1 ]
Wei, Zhonglin [1 ]
Cao, Jungang [1 ]
Liang, Dapeng [1 ]
Duan, Haifeng [1 ]
Lin, Yingjie [1 ]
机构：
[1] Jilin Univ, Dept Organ Chem, Coll Chem, Changchun 130012, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 23期
基金：
中国国家自然科学基金;
关键词：
LAMELLARIN ALPHA 20-SULFATE; CARDUUS-CRISPUS; DOUBLE-BONDS; DERIVATIVES; ALKALOIDS; RADICALS; ANALOGS; CASCADE; AMINES;
D O I：
10.1021/acs.joc.6b01781
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a new base-promoted intermolecular cascade cyclization reaction of substituted 3-aryl(heteroaryl)-3-chloroacrylaldehydes and tetrahydroisoquinolines in one pot. The reaction provides a facile and practical synthesis of pyrrolo[2,1-a]isoquinolines. A number of pyrrolo[2,1-a]isoquinolines were synthesized in moderate to high yields (up to 97%).
引用
收藏
页码：11950 / 11955
页数：6
相关论文
共 34 条
  • [1] 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
    [J]. RSC ADVANCES, 2013, 3 (04): : 1089 - 1096
  • [2] 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
  • [3] DABCO and DMAP - Why are they different in organocatalysis?
    Baidya, Mahiuddin
    Kobayashi, Shinjiro
    Brotzel, Frank
    Schmidhammer, Uli
    Riedle, Eberhard
    Mayr, Herbert
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (32) : 6176 - 6179
  • [4] Bailey K. R., 2007, J CHEM SOC CHEM COMM, P3640
  • [5] Baylis-Hillman Acetates in Synthesis: Copper(I)/tert-Butyl Hydroperoxide Promoted One-Pot Oxidative Intramolecular Cyclization Protocol for the Preparation of Pyrrole-Fused Compounds and the Formal Synthesis of (±)-Crispine A
    Basavaiah, Deevi
    Lingaiah, Balthu
    Reddy, Guddeti Chandrashekar
    Sahu, Bharat Chandra
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) : 2398 - 2403
  • [6] Retro-Claisen condensation versus pyrrole formation in reactions of amines and 1,3-diketones
    Deb, Indubhusan
    Seidel, Daniel
    [J]. TETRAHEDRON LETTERS, 2010, 51 (22) : 2945 - 2947
  • [7] Stereochemical Course of Baker's Yeast Mediated Reduction of the Tri- and Tetrasubstituted Double Bonds of Substituted Cinnamaldehydes
    Fronza, Giovanni
    Fuganti, Claudio
    Serra, Stefano
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) : 6160 - 6171
  • [8] A general, simple and green process to access pyrrolo[2,1-a]isoquinolines using a KI/TBHP catalytic system
    Huang, Huan-Ming
    Huang, Fang
    Li, Yu-Jin
    Jia, Jian-Hong
    Ye, Qing
    Han, Liang
    Gao, Jian-Rong
    [J]. RSC ADVANCES, 2014, 4 (52) : 27250 - 27258
  • [9] Iodine-Catalyzed 1,3-Dipolar Cycloaddition/Oxidation/Aromatization Cascade with Hydrogen Peroxide as the Terminal Oxidant: General Route to Pyrrolo[2,1-a]isoquinolines
    Huang, Huan-Ming
    Li, Yu-Jin
    Ye, Qing
    Yu, Wu-Bin
    Han, Liang
    Jia, Jian-Hong
    Gao, Jian-Rong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) : 1084 - 1092
  • [10] Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues
    Kamiyama, Haruka
    Kubo, Yoshinao
    Sato, Hironori
    Yamamoto, Naoki
    Fukuda, Tsutomu
    Ishibashi, Fumito
    Iwao, Masatomo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (24) : 7541 - 7550
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