Synthesis of Azocino[5,4-b]indoles via Gold-Catalyzed Intramolecular Alkyne Hydroarylation

被引：71
|
作者：
Peshkov, Vsevolod A. [1 ]
Pereshivko, Olga P. [1 ]
Van der Eycken, Erik V. [1 ]
机构：
[1] Univ Leuven KU Leuven, LOMAC, Dept Chem, B-3001 Louvain, Belgium
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 14-15期
关键词：
C?C coupling; cyclization; gold catalysis; medium-ring compounds; nitrogen heterocycles; INTERMOLECULAR REACTIONS; FUSED HETEROCYCLES; CYCLIZATION; INDOLES; DERIVATIVES; EFFICIENT; REARRANGEMENT; CONSTRUCTION; 1,4-DIYNES; SYSTEMS;
D O I：
10.1002/adsc.201200305
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient procedure for the synthesis of the azocino[5,4-b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2-propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury(II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.
引用
收藏
页码：2841 / 2848
页数：8
相关论文
共 50 条
  • [41] Rhodium(III)-catalyzed intramolecular amidoarylation and hydroarylation of alkyne via C-H activation: switchable synthesis of 3,4-fused tricyclic indoles and chromans
    Zhang, Xue
    Li, Yifei
    Shi, Hui
    Zhang, Lunan
    Zhang, Shanshan
    Xu, Xianxiu
    Liu, Qun
    CHEMICAL COMMUNICATIONS, 2014, 50 (55) : 7306 - 7309
  • [42] Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
    Thilmany, Pierre
    Guarnieri-Ibanez, Alejandro
    Jacob, Clement
    Lacour, Jerome
    Evano, Gwilherm
    ACS ORGANIC & INORGANIC AU, 2022, 2 (01): : 53 - 58
  • [43] PtIV-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation
    Pastine, SJ
    Youn, SW
    Sames, D
    ORGANIC LETTERS, 2003, 5 (07) : 1055 - 1058
  • [44] Direct Synthesis of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Diynes
    Hirano, Kimio
    Inaba, Yusuke
    Takahashi, Naoya
    Shimano, Masanao
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05): : 1212 - 1227
  • [45] Gold-Catalyzed Intramolecular Dearomatization of Phenols with Allenoates for the Synthesis of Spirocyclohexadienones
    Wang, Hongyu
    Wang, Kaiye
    Xiang, Yanan
    Jiang, Han
    Wan, Xiuyan
    Li, Na
    Tang, Bo
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (12) : 2352 - 2357
  • [46] Synthesis of functionalized indolizines via gold(I)-catalyzed intramolecular hydroarylation/aromatization of pyrrole-ynes
    Li, Xiangdong
    Zhao, Jidong
    Xie, Xin
    Liu, Yuanhong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (38) : 8119 - 8133
  • [47] Gold-catalyzed approach to the synthesis of Echinopines A and B
    Dorel, Ruth
    Echavarren, Antonio
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [48] Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation
    Wu Yundong
    Peng Sha
    Ouyang Yuejun
    Qian Pengcheng
    He Weimin
    Xiang Jiannan
    ACTA CHIMICA SINICA, 2012, 70 (12) : 1367 - 1370
  • [49] Divergent Synthesis of Isoxazolo[5,4-b]pyridines
    Li, Min
    Li, Wenzhe
    Huang, Min
    Zhang, Xiaomei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (09)
  • [50] NOVEL SYNTHESIS OF ISOXAZOLO[5,4-B]QUINOLINES
    NEELIMA
    BHAT, B
    BHADURI, AP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (05) : 1469 - 1472
12345