Synthesis of α-carbolines by copper-catalyzed radical cyclization β-(3-indolyl) ketone O-pentafluorobenzoyloximes

被引：33
|
作者：
Tanaka, K [1 ]
Kitamura, M [1 ]
Narasaka, K [1 ]
机构：
[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2005年 / 78卷 / 09期
关键词：
D O I：
10.1246/bcsj.78.1659
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Radical cyclization of beta-(3-indolyl) ketone O-pentafluorobenzoyloximes proceeds by the treatment with a catalytic amount of copper powder in 1,2-dichloroethane to generate 3,4-dihydro-alpha-carbolines, which are oxidized to alpha-carbolines with chloranil.
引用
收藏
页码：1659 / 1664
页数：6
相关论文
共 50 条
  • [1] Synthesis of pyrrole derivatives by palladium-catalyzed cyclization of γδ-unsaturated ketone O-pentafluorobenzoyloximes
    Tsutsui, H
    Kitamura, M
    Narasaka, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (07) : 1451 - 1460
  • [2] Synthesis of pyridine and isoquinoline derivatives by the palladium-catalyzed cyclization of olefinic ketone O-pentafluorobenzoyloximes
    Tsutsui, H
    Narasaka, K
    CHEMISTRY LETTERS, 2001, (06) : 526 - 527
  • [3] Synthesis of polycyclic Imines by palladium-catalyzed domino cyclization of Di- and trienyl ketone O-pentafluorobenzoyloximes
    Zaman, S
    Kitamura, M
    Narasaka, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (05) : 1055 - 1062
  • [4] Synthesis of 1-azaazulenes from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by palladium-catalyzed cyclization and oxidation
    Chiba, S
    Kitamura, M
    Saku, O
    Narasaka, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (04) : 785 - 796
  • [5] Synthesis of pyrrole derivatives by the Heck-type cyclization of γ,δ-unsaturated ketone O-pentafluorobenzoyloximes
    Tsutsui, H
    Narasaka, K
    CHEMISTRY LETTERS, 1999, (01) : 45 - 46
  • [6] Synthesis of α-carbolines from β-(3-Indolyl) ketone O-2,4-dinitrophenyloximes
    Ono, A
    Narasaka, K
    CHEMISTRY LETTERS, 2001, (02) : 146 - 147
  • [7] Radical Cyclization of O-pentafluorobenzoyloximes having a (cyclohexadiene)Fe(CO)3 moiety
    Tanaka, K
    Yukimura, N
    Narasaka, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (03) : 575 - 584
  • [8] Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes
    Zhang, HM
    Larock, RC
    TETRAHEDRON LETTERS, 2002, 43 (08) : 1359 - 1362
  • [9] Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes
    Zhang, HM
    Larock, RC
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7048 - 7056
  • [10] Copper-Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines
    Xu, Miao
    Jiang, Jia-Tian
    Dong, Hao-Xuan
    Wang, Guang-Hui
    Zhou, Bo
    Ye, Long-Wu
    ADVANCED SYNTHESIS & CATALYSIS, 2025, 367 (02)
12345