Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes

被引:117
|
作者
Zhang, HM [1 ]
Larock, RC [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/ol010124w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A variety of substituted beta- and gamma -carbolines have been prepared in good to excellent yields by the annulation of internal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively, in the presence of a palladium catalyst.
引用
收藏
页码:3083 / 3086
页数:4
相关论文
共 50 条
  • [31] Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes
    Larock, RC
    Yum, EK
    Refvik, MD
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22): : 7652 - 7662
  • [32] Synthesis of coumarins via palladium-catalyzed carbonylative annulation of internal alkynes by o-iodophenols
    Kadnikov, DV
    Larock, RC
    ORGANIC LETTERS, 2000, 2 (23) : 3643 - 3646
  • [33] Palladium-catalyzed carbonylative annulation of internal alkynes: Synthesis of 3,4-disubstituted coumarins
    Kadnikov, DV
    Larock, RC
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24): : 9423 - 9432
  • [34] Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes
    Satoh, T
    Ogino, S
    Miura, M
    Aromitra, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) : 5063 - 5065
  • [35] Applications of the palladium-catalyzed carbonylative annulation of internal alkynes to the synthesis of medium-sized rings
    Kadnikov, Dmitry V.
    Larock, Richard C.
    MENDELEEV COMMUNICATIONS, 2007, 17 (02) : 74 - 76
  • [36] Palladium-Catalyzed anti-Selective Fluoroalkylboration of Internal and Terminal Alkynes
    Wang, Shuaifeng
    Zhang, Jian
    Kong, Lichun
    Tan, Ze
    Bai, Yihui
    Zhu, Gangguo
    ORGANIC LETTERS, 2018, 20 (18) : 5631 - 5635
  • [37] Palladium-Catalyzed Annulation of Internal Alkynes: Direct Access to π-Conjugated Ullazines
    Wan, Danyang
    Li, Xiaoyu
    Jiang, Ruyong
    Feng, Boya
    Lan, Jingbo
    Wang, Ruilin
    You, Jingsong
    ORGANIC LETTERS, 2016, 18 (12) : 2876 - 2879
  • [38] Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds
    Yang, Xi
    Wang, Gang
    Ye, Zhi-Shi
    CHEMICAL SCIENCE, 2022, 13 (34) : 10095 - 10102
  • [39] Palladium-Catalyzed Oxidative Synthesis of -Acetoxylated Enones from Alkynes
    Jiang, Tuo
    Quan, Xu
    Zhu, Can
    Andersson, Pher G.
    Backvall, Jan-E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (19) : 5824 - 5828
  • [40] Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions
    Ibrahim, Mansur B.
    El Ali, Bassam
    Malik, Imran
    Fettouhi, Mohammed
    TETRAHEDRON LETTERS, 2016, 57 (05) : 554 - 558