Radical cascade involving a 5-endo-trig cyclization of α-amidoyl radicals

被引：30
|
作者：
Ishibashi, H [1 ]
Ishita, A [1 ]
Tamura, O [1 ]
机构：
[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 03期
关键词：
aryl halides; enamides; cyclisation; radical and radical reactions;
D O I：
10.1016/S0040-4039(01)02200-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bu3SnH-mediated radical reactions of aryl bromides 4 gave pyrrolo[1,2-b]- and isoindolo[2, I -b]isoquinoline derivatives 11 through a radical cascade process involving a 6-endo-trig cyclization of an aryl radical and a 5-endo-trig cyclization of an alpha-amidoyl radical. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：473 / 475
页数：3
相关论文
共 50 条
  • [1] 5-Endo-trig radical cyclizations
    Ishibashi, H
    Sato, T
    Ikeda, M
    [J]. SYNTHESIS-STUTTGART, 2002, (06): : 695 - 713
  • [2] Recent advances of 5-endo-trig radical cyclization: promoting strategies and applications
    Zhou, Yulu
    Xu, Sangxuan
    Zhang, Xuemei
    Zhou, Lanxi
    Zheng, Hanliang
    Zhu, Gangguo
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (74) : 10098 - 10111
  • [3] Synthesis of pterocarpans by means of a "disfavored" 5-endo-trig radical cyclization reaction
    Santhosh, KC
    Gopalsamy, A
    Balasubramanian, KK
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (18) : 3461 - 3466
  • [4] Short Formal Syntheses of Lycorine and Congeners Using a 5-Endo-Trig/6-Endo-Trig Radical Cyclization Sequence
    Tan, Shen
    Zard, Samir Z.
    Pham, Le Nhan
    Coote, Michelle L.
    Banwell, Martin G.
    Lan, Ping
    White, Lorenzo V.
    [J]. ORGANIC LETTERS, 2024, 26 (20) : 4292 - 4296
  • [5] Recent Advances on 5-endo-Trig Radical Cyclization of All-Carbon Systems
    Zheng Hanliang
    Su Jingwen
    Zhou Yulu
    Zhu Gangguo
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 4060 - 4066
  • [6] Electrochemical catalysis of a 5-endo-trig cyclization in bicontinuous microemulsions
    Gao, JX
    Rusling, JF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02): : 218 - 219
  • [7] 5-endo-trig radical cyclizations:: Disfavored or favored processes?
    Chatgilialoglu, C
    Ferreri, C
    Guerra, M
    Timokhin, V
    Froudakis, G
    Gimisis, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (36) : 10765 - 10772
  • [8] Anionic 5-endo-trig cyclization of terminally difluorinated homoallylic alkoxides
    Yamazaki, T
    Hiraoka, S
    Sakamoto, J
    Kitazume, T
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (34): : 6820 - 6824
  • [9] Computational interpretations on 5-endo-trig cyclization of terminally difluorinated homoallylic alkoxides
    Yamazaki, T
    Hiraoka, S
    Sakamoto, J
    Kitazume, T
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2000, 101 (02) : 309 - 313
  • [10] Effect of propargylic substitution on the 5-endo-trig cyclization of bromomethyldimethylsilyl propargyl ethers
    Bogen, Stephane
    Goddard, Jean-Philippe
    Fensterbank, Louis
    Malacria, Max
    [J]. ARKIVOC, 2008, : 126 - 138
12345