Formal [4+2] Reaction between 1,3-Diynes and Pyrroles: Gold(I)-Catalyzed Indole Synthesis by Double Hydroarylation

被引:82
|
作者
Matsuda, Yuka [1 ]
Naoe, Saori [1 ]
Oishi, Shinya [1 ]
Fujii, Nobutaka [1 ]
Ohno, Hiroaki [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
基金
日本学术振兴会;
关键词
carbazoles; cascade reaction; gold catalysis; hydroarylation; indoles; HOMOGENEOUS GOLD CATALYSIS; ONE-POT SYNTHESIS; POLYCYCLIC COMPOUNDS; HYDROAMINATION; CONSTRUCTION; CASCADE; ALKYNES; CYCLIZATION; INHIBITORS; ALKALOIDS;
D O I
10.1002/chem.201405903
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indole synthesis by a gold(I)-catalyzed intermolecular formal [4+2] reaction between 1,3-diynes and pyrroles has been developed. This reaction involves the hydroarylation of 1,3-diynes with pyrroles followed by an intramolecular hydroarylation to give the 4,7-disubstituted indoles. This reaction can also be applied to the synthesis of carbazoles when indoles are used as the nucleophiles instead of pyrroles.
引用
收藏
页码:1463 / 1467
页数:5
相关论文
共 50 条
  • [41] Visible-light-catalyzed synthesis of 1,3-benzoxazines via formal [4+2] cycloaddition of oximes with o-hydroxybenzyl alcohols
    Qi, Zhenjie
    An, Zhenyu
    Huang, Bingbing
    Wu, Mingzhong
    Wu, Quansen
    Jiang, Dongfang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (31) : 6419 - 6423
  • [42] Synthesis of 2-cyclohexenone derivatives via gold(I)-catalyzed hydrative cyclization of 1,6-diynes
    Zhang, Chen
    Cui, Dong-Mei
    Yao, Li-Ying
    Wang, Bi-Song
    Hu, Yong-Zhou
    Hayashi, Teruyuki
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19): : 7811 - 7813
  • [43] Ruthenium-Catalyzed trans-Hydrogermylation of Alkynes: Formation of 2,5-Disubstituted Germoles through Double trans-Hydrogermylation of 1,3-Diynes
    Matsuda, Takanori
    Kadowaki, Sho
    Yamaguchi, Yoshiyuki
    Murakami, Masahiro
    ORGANIC LETTERS, 2010, 12 (05) : 1056 - 1058
  • [44] Gold-Catalyzed Cadiot-Chodkiewicz-type Cross-Coupling of Terminal Alkynes with Alkynyl Hypervalent Iodine Reagents: Highly Selective Synthesis of Unsymmetrical 1,3-Diynes
    Li, Xiangdong
    Xie, Xin
    Sun, Ning
    Liu, Yuanhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (24) : 6994 - 6998
  • [45] Ni-Catalyzed Defluorination for the Synthesis of gem-Difluoro-1,3-dienes and Their [4+2] Cycloaddition Reaction
    Zhou, Minqi
    Zhang, Jian
    Zhang, Xing-Guo
    Zhang, Xingang
    ORGANIC LETTERS, 2019, 21 (03) : 671 - 674
  • [46] Rh(i)-Catalyzed enantioselective and scalable [4+2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates
    Bao, Robert Li-Yuan
    Yin, Junjie
    Shi, Lei
    Zheng, Limin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2956 - 2961
  • [47] Synthesis of Tetrahydropyridazine Amino Acid Derivatives by a Formal [4+2] Cycloaddition Reaction of 1,2-Diaza-1,3-dienes with Dehydroalanine Esters
    Attanasi, Orazio A.
    Favi, Gianfranco
    Giorgi, Gianluca
    Mantellini, Fabio
    Moscatelli, Giada
    Piersanti, Giovanni
    CURRENT ORGANIC SYNTHESIS, 2013, 10 (05) : 803 - 811
  • [48] Synthesis of Densely Substituted Pyridine Derivatives from 1-Methyl-1,3-(ar)enynes and Nitriles by a Formal [4+2] Cycloaddition Reaction
    He, Dandan
    Wang, Bowen
    Duan, Kanghui
    Zhou, Yang
    Li, Meng
    Jiang, Huanfeng
    Wu, Wanqing
    ORGANIC LETTERS, 2022, 24 (06) : 1292 - 1297
  • [49] Synthesis of 2-Aminopyrrolo[1,2-b]pyridazines via Gold(I)-Catalyzed Chemoselective Hydroamination/Hydroarylation Cascade of 1,3-Diynamides with 1-Aminopyrroles
    Wang, Junying
    Du, Jianghui
    Wang, Tao
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (07) : 1088 - 1092
  • [50] Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles
    Sahani, Rajkumar Lalji
    Liu, Rai-Shung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (04) : 1026 - 1030