Reactions of 1,2-bis(1H-indol-2-yl)ethane:: Formation of indolo[2,3-c]carbazole and cyclohept[1,2-b:5,4-b′]bisindole derivatives

被引:18
作者
Bergman, J
Janosik, T
Yudina, L
Desarbre, E
Lidgren, G
Venemalm, L
机构
[1] Karolinska Inst, Novum, Dept Biosci, CNT,Unit Organ Chem, SE-14157 Huddinge, Sweden
[2] Sodertorn Univ Coll, SE-14104 Huddinge, Sweden
关键词
indolocarbazoles; bisindoles;
D O I
10.1016/S0040-4020(00)00100-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared and converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4-b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1911 / 1916
页数:6
相关论文
共 37 条
  • [1] [Anonymous], 1993, STUDIES NATURAL PROD
  • [2] REACTIVITY OF 2H-1,2,3-DIAZAPHOSPHOLE DERIVATIVES - UNEXPECTED FORMATION OF INDOLES AND A NEW INDOLIZATION REACTION
    BACCOLINI, G
    TODESCO, PE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (03): : 535 - 538
  • [3] REACTION OF SOME INDOLES AND INDOLINES WITH 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE
    BERGMAN, J
    CARLSSON, R
    MISZTAL, S
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (09): : 853 - 862
  • [4] Synthesis of indolo[3,2-a]pyrrolo[3,4-c]carbazole in one step from indole and maleimide
    Bergman, J
    Desarbre, E
    Koch, E
    [J]. TETRAHEDRON, 1999, 55 (08) : 2363 - 2370
  • [5] STRUCTURE ELUCIDATION OF SOME PRODUCTS OBTAINED BY ACID-CATALYZED CONDENSATION OF INDOLE WITH ACETONE
    BERGMAN, J
    NORRBY, PO
    TILSTAM, U
    VENEMALM, L
    [J]. TETRAHEDRON, 1989, 45 (17) : 5549 - 5564
  • [6] Bergman J, 1997, HETEROCYCL COMMUN, V3, P397
  • [7] CHEN YH, 1995, J BIOL CHEM, V270, P22584
  • [8] STERIC EFFECTS - INVERSION OF 4,5-DISUBSTITUTED 9,10-DIHYDROPHENANTHRENES
    COSMO, R
    STERNHELL, S
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (01) : 35 - 47
  • [9] Synthesis of symmetric and non-symmetric indolo[2,3-c]carlbazole derivatives:: preparation of indolo[2,3-c]pyrrolo[3,4-a]carbazoles
    Desarbre, E
    Bergman, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (13): : 2009 - 2016
  • [10] K252A IS A POTENT AND SELECTIVE INHIBITOR OF PHOSPHORYLASE-KINASE
    ELLIOTT, LH
    WILKINSON, SE
    SEDGWICK, AD
    HILL, CH
    LAWTON, G
    DAVIS, PD
    NIXON, JS
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 171 (01) : 148 - 154