[4+2]cycloaddition of indole derivatives with bismaleimides: A route to new biscarbazoles

被引:13
|
作者
Pindur, U
Gonzalez, E
Mehrabani, F
机构
[1] Institute of Pharmacy, Department of Chemistry and Pharmacy, University of Mainz
关键词
D O I
10.1039/a608580f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New results for the reaction of in situ generated N-acylindole-2,3-quinodimethanes and donor-/acceptor-substituted 3-vinylindoles with some bismaleimides are described. By a [4 + 2]cycloaddition process, a variety of biscarbazoles are formed endo-selectively. These conformationally flexible molecules constitute a new class of compounds believed to have potential as DNA minor groove binding ligands.
引用
收藏
页码:1861 / 1867
页数:7
相关论文
共 50 条
  • [21] [4+2]CYCLOADDITION OF MONOCYCLIC IMIDAZOLE DERIVATIVES WITH ELECTRON-DEFICIENT ACETYLENES
    YAMAZAKI, C
    KATAYAMA, K
    SUZUKI, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3085 - 3089
  • [22] Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives
    Song Chunlan
    Liu Kun
    Jiang Xu
    Dong Xin
    Weng Yue
    Chiang Chien-Wei
    Lei Aiwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (18) : 7193 - 7197
  • [23] [4+2] CYCLOADDITION REACTIONS OF TRIARYLPHOSPHAALKENES
    VANDERKNAAP, TA
    KLEBACH, TC
    VISSER, F
    LOURENS, R
    BICKELHAUPT, F
    TETRAHEDRON, 1984, 40 (06) : 991 - 997
  • [24] A new procedure for the preparation of 2-vinylindoles and their [4+2] cycloaddition reaction
    Mohamed, Yaseen Ali Mosa
    Inagaki, Fuyuhiko
    Takahashi, Ryohei
    Mukai, Chisato
    TETRAHEDRON, 2011, 67 (29) : 5133 - 5141
  • [25] SYNTHESIS OF SOME NEW POLYNUCLEAR COMPOUNDS BY [4+2] CYCLOADDITION REACTION
    SAMANTA, SR
    MUKHERJEE, AK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1987, 26 (01): : 26 - 29
  • [26] SYNTHESIS OF SOME NEW POLYNUCLEAR COMPOUNDS BY [4+2]-CYCLOADDITION REACTION
    SAMANTA, SR
    MUKHERJEE, AK
    BHATTACHARYYA, AJ
    CURRENT SCIENCE, 1988, 57 (17): : 926 - 931
  • [27] COMPETITIVE INTRAMOLECULAR [4+2] CYCLOADDITION AND [2+2] CYCLOADDITION OF SULFONYLALLENE
    KANEMATSU, K
    SUGIMOTO, N
    KAWAOKA, M
    YEO, S
    SHIRO, M
    TETRAHEDRON LETTERS, 1991, 32 (10) : 1351 - 1354
  • [28] Synthesis of isoindolinones: Intramolecular [4+2] cycloaddition/retro [4+2] of pyridone propiolamides
    Wilson, Jonathan E.
    Garvey, Joshua
    Taveras, Kennedy M.
    TETRAHEDRON LETTERS, 2019, 60 (41)
  • [29] Mechanistic Insights into the Stepwise (4+2) Cycloaddition toward Chiral Fused Uracil Derivatives
    Marcantonio, Enrico
    Zanardi, Franca
    Curti, Claudio
    Lombardo, Marco
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (09) : 1531 - 1539
  • [30] Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives
    Wang, Leifeng
    Wu, Fengjin
    Chen, Jiean
    Nicewicz, David A.
    Huang, Yong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (24) : 6896 - 6900