Construction of 9H-Pyrrolo[1,2-a]indoles by a Copper-Catalyzed Friedel-Crafts Alkylation/Annulation Cascade Reaction

被引：28
|
作者：
Sun, Yongqing [1 ]
Qiao, Yu [1 ]
Zhao, Haiying [1 ]
Li, Baoguo [1 ]
Chen, Shufeng [1 ]
机构：
[1] Inner Mongolia Univ, Dept Chem & Chem Engn, Inner Mongolia Key Lab Fine Organ Synth, Hohhot 010021, 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：
CONDENSED N-HETEROCYCLES; INDOLES; DERIVATIVES; CYCLOADDITIONS; ACCESS;
D O I：
10.1021/acs.joc.6b02143
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and concise Cu(OTf)(2)-catalyzed Friedel Crafts alkylation/annulation cascade reaction of substituted indoles with 1,2-dicarbony1-3-enes has been established. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of diverse 9H-pyrrolo[1,2-a]indoles bearing a carbonyl group.
引用
收藏
页码：11987 / 11993
页数：7
相关论文
共 50 条
  • [41] Divergent Syntheses of Isoquinolines and Indolo[1,2-a]quinazolines by Copper-Catalyzed Cascade Annulation from 2-Haloaryloxime Acetates with Active Methylene Compounds and Indoles
    Jiang, Huanfeng
    Yang, Jidan
    Tang, Xiaodong
    Wu, Wanqing
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05): : 2053 - 2061
  • [42] Copper-Catalyzed Cascade Phosphorylation Initiated Radical Cyclization: Access to 2-Phosphorylated Pyrrolo[1,2-a]indole
    Zhang, Honglin
    Li, Weipeng
    Zhu, Chengjian
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04): : 2199 - 2204
  • [43] Chiral Bronsted acid catalyzed intermolecular Friedel-Crafts alkylation of styrenes with indoles: construction of all-carbon quaternary stereocenters
    Li, Ming-Li
    Chen, Dian-Feng
    Luo, Shi-Wei
    Wu, Xiang
    TETRAHEDRON-ASYMMETRY, 2015, 26 (04) : 219 - 224
  • [44] Cascade Phosphinoylation/Cyclization/Isomerization Process for the Synthesis of 2-Phosphinoyl-9H-pyrrolo[1,2-a]indoles
    Chen, Su
    Zhang, Pengbo
    Shu, Wanyun
    Gao, Yuzhen
    Tang, Guo
    Zhao, Yufen
    ORGANIC LETTERS, 2016, 18 (21) : 5712 - 5715
  • [45] Synthesis of Indolo[1,2-b]isoquinoline Derivatives by Lewis Acid-Catalyzed Intramolecular Friedel-Crafts Alkylation Reaction
    Gour, Jitendra
    Gatadi, Srikanth
    Nagarsenkar, Atulya
    Babu, Bathini Nagendra
    Madhavi, Y. V.
    Nanduri, Srinivas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (22) : 2817 - 2821
  • [46] Synthesis of 9H-Pyrrolo[1,2-a]indole and 3H-Pyrrolizine Derivatives via a Phosphine-Catalyzed Umpolung Addition/Intramolecular Wittig Reaction
    Saleh, Nidal
    Voituriez, Arnaud
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4371 - 4377
  • [47] Synthesis of dihydroindeno[1,2-c] isochromene via cascade cyclization and Friedel-Crafts reaction
    Saikia, Anil K.
    Ghosh, Priya
    Deka, Manash Jyoti
    Borah, Madhurjya
    RSC ADVANCES, 2016, 6 (108): : 106656 - 106661
  • [48] Chiral bronsted acid catalyzed enantioselective Friedel-Crafts reaction of indoles and α-aryl enamides:: Construction of quaternary carbon atoms
    Jia, Yi-Xia
    Zhong, Jun
    Zhu, Shou-Fei
    Zhang, Can-Ming
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5565 - 5567
  • [49] Sequential aza-Piancatelli rearrangement/Friedel-Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives
    Reddy, B. V. Subba
    Reddy, Y. Vikram
    Singarapu, Kiran Kumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (03) : 1111 - 1116
  • [50] Synthesis of Tetrahydro-1H-indeno[1,2-b]pyridine via Cascade Cyclization and Friedel-Crafts Reaction
    Borthakur, Upasana
    Borah, Madhurjya
    Deka, Manash J.
    Saikia, Anil K.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 8736 - 8743
12345