Fe(OTf)3 Catalyzed Annulation of 2,3-Disubstituted Indoles with Aziridines

被引：18
|
作者：
Liu, Hua [1 ]
Zheng, Chao [1 ]
You, Shu-Li [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2014年 / 32卷 / 08期
关键词：
annulation; indole; aziridine; Lewis acid; catalysis; ALLYLIC DEAROMATIZATION REACTION; FORMAL 3+2 CYCLOADDITION; CARBON BOND-CLEAVAGE; ENANTIOSELECTIVE SYNTHESIS; CASCADE DEAROMATIZATION; CYCLOPENTANNULATION; PYRROLOINDOLINES; CYCLIZATION; TRYPTOPHOLS; ALKALOIDS;
D O I：
10.1002/cjoc.201400178
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Fe(OTf)(3) catalyzed [3+2] annulation reaction between 2,3-disubstituted indoles and N-Ts aziridines is described herein. A series of hexahydropyrrolo[3,4-b]indole derivatives bearing two consecutive quaternary carboncenters can be generated efficiently. The reaction features cheap catalyst, mild conditions and operational simplicity.
引用
收藏
页码：709 / 714
页数：6
相关论文
共 50 条
  • [41] A novel route to 2,3-disubstituted indoles via palladium-catalyzed three-component coupling of aryl iodide, o-alkenylphenyl isocyanide and amine
    Onitsuka, K
    Suzuki, S
    Takahashi, S
    TETRAHEDRON LETTERS, 2002, 43 (35) : 6197 - 6199
  • [42] Syntheses of Spiro[cyclopent[3]ene-1,3′-indole]s and Tetrahydrocyclohepta[b]indoles from 2,3-Disubstituted Indoles through Sigmatropic Rearrangement
    Chakraborty, Amrita
    Goswami, Koushik
    Adiyala, Akhila
    Sinha, Surajit
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (31) : 7117 - 7127
  • [43] Synthesis of 3-Substituted and 2,3-Disubstituted Quinazolinones via Cu-Catalyzed Aryl Amidation
    Xu, Lanting
    Jiang, Yongwen
    Ma, Dawei
    ORGANIC LETTERS, 2012, 14 (04) : 1150 - 1153
  • [44] Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines
    Suzuki, Tamie
    Mate, Nilamber A.
    Adhikari, Arijit A.
    Chisholm, John D.
    MOLECULES, 2019, 24 (22):
  • [45] Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines
    Sun, Hongnan
    Huang, Binbin
    Lin, Run
    Yang, Chao
    Xia, Wujiong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 524 - 529
  • [46] Acid-catalyzed highly diastereoselective and effective synthesis of 1,3-disubstituted tetrahydropyrano[3,4-b]indoles
    Wang, Pei
    Zhao, Jia-Zhen
    Li, Hong-Feng
    Liang, Xiang-Ming
    Zhang, Ya-Lun
    Da, Chao-Shan
    TETRAHEDRON LETTERS, 2017, 58 (02) : 129 - 133
  • [47] Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity
    Daly, Seth
    Hayden, Kathryn
    Malik, Indranil
    Porch, Nikki
    Tang, Hong
    Rogelj, Snezna
    Frolova, Liliya V.
    Lepthien, Katrina
    Kornienko, Alexander
    Magedov, Igor V.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (16) : 4720 - 4723
  • [48] A Flexible Synthesis of 2,3-Disubstituted Indoles from Aminobenzyl Phosphonium Salts. A Direct Synthesis of Rutaecarpine
    Kraus, George A.
    Guo, Haitao
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5337 - 5341
  • [49] Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles
    Liu, Tingting
    Wang, Jianbin
    Xiao, Rou
    Zhao, Junling
    RSC ADVANCES, 2024, 14 (22) : 15591 - 15596
  • [50] A mild and efficient synthesis of 2,5-disubstituted 2,3-dihydro-4-pyridones catalyzed by Yb(OTf)3
    Cheng, K
    Zeng, BQ
    Yu, ZP
    Gao, B
    Feng, XM
    SYNLETT, 2005, (06) : 1018 - 1020
12345