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
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
  • [21] Palladium-catalyzed synthesis of 2,3-disubstituted indoles via arylation of ortho-alkynylanilines with arylsiloxanes
    Hsia, Yang-Ting
    Lu, Yu-Lin
    Bai, Rekha
    Badsara, Satpal Singh
    Lee, Chin-Fa
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (37) : 7602 - 7610
  • [22] Efficient synthesis of 2-mono and 2,3-disubstituted indoles via palladium-catalyzed oxidation of aminoalcohols
    Aoyagi, Yutaka
    Shishikura, Masahiro
    Mizusaki, Toshihiko
    Komine, Takashi
    Yoshinaga, Tokuji
    Inaba, Haruko
    Ohta, Akihiro
    Takeya, Koichi
    HETEROCYCLES, 2008, 75 (05) : 1055 - 1059
  • [23] Concise Synthesis of Polycyclic Indoline Scaffolds through an InIII-Catalyzed Formal [4+2] Annulation of 2,3-Disubstituted Indoles with o-Aminobenzyl Alcohols
    Luo, Mupeng
    Chen, Jianxin
    Yu, Linqian
    Wei, Wanguo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (18) : 2652 - 2660
  • [24] Recyclable CuFe2O4 for the synthesis of 2,3-disubstituted indoles
    Vu, Cuong M.
    Le, Khoa B.
    Vo, Uyen N.
    Van, Vy D. T.
    Nguyen, Anh T.
    Phan, Nam T. S.
    Le, Nhan T. H.
    Nguyen, Tung T.
    TETRAHEDRON LETTERS, 2020, 61 (50)
  • [25] Computational study on the NHC-catalyzed synthesis of 2,3-disubstituted indoles: mechanism, key intermediate and the role of the catalyst
    Tu, Peng-Cheng
    Zhou, Lin
    Kirillov, Alexander M.
    Fang, Ran
    Yang, Lizi
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1356 - 1365
  • [26] Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds
    Guo, Xin
    Han, Jianwei
    Liu, Yafeng
    Qin, Mingda
    Zhang, Xueguo
    Chen, Baohua
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21) : 11505 - 11511
  • [27] Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles
    Li, Weishuang
    Dong, Zhan
    Zhang, Yan
    Zeng, Zhen
    Usman, Muhammad
    Liu, Wen-Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) : 7995 - 8005
  • [28] Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines
    Ma, Wei-Yang
    Gelis, Coralie
    Bouchet, Damien
    Retailleau, Pascal
    Moreau, Xavier
    Neuville, Luc
    Masson, Geraldine
    ORGANIC LETTERS, 2021, 23 (02) : 442 - 448
  • [29] Synthesis of 2,3-disubstituted indoles from alkynylanilines and 2-chlorophenols using palladium-dihydroxyterphenylphosphine catalyst
    Yamaguchi, Miyuki
    Ogihara, Kota
    Konishi, Hideyuki
    Manabe, Kei
    TETRAHEDRON LETTERS, 2020, 61 (21)
  • [30] Antiproliferative activity of 2,3-disubstituted indoles toward apoptosis-resistant cancers cells
    Magedov, Igor V.
    Lefranc, Florence
    Frolova, Liliya V.
    Banuls, Laetitia Moreno Y.
    Peretti, Amanda S.
    Rogelj, Snezna
    Mathieu, Veronique
    Kiss, Robert
    Kornienko, Alexander
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (11) : 3277 - 3282