Expedient, one-pot preparation of fused indoles via CAN-catalyzed three-component domino sequences and their transformation into polyheterocyclic compounds containing pyrrolo[1,2-a]azepine fragments

被引:50
作者
Suryavanshi, Padmakar A. [1 ]
Sridharan, Vellaisamy [1 ]
Carlos Menendez, J. [1 ]
机构
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
关键词
CERIUM(IV) AMMONIUM-NITRATE; RING-CLOSING METATHESIS; NONREARRANGED MONOTERPENOID UNIT; NENITZESCU REACTION; MULTICOMPONENT REACTIONS; PRIVILEGED STRUCTURES; HUMAN; 5-LIPOXYGENASE; MEDICINAL CHEMISTRY; NATURAL-PRODUCTS; DRUG DISCOVERY;
D O I
10.1039/c004703a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The CAN-catalyzed three-component between reaction between primary amines, beta-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g]indole systems through a gamma-alkylation/ring-closing metathesis sequence.
引用
收藏
页码:3426 / 3436
页数:11
相关论文
共 60 条
  • [1] Chemoenzymatic synthesis of deoxy analogues of the DNA topoisomerase II inhibitor eleutherin and the 3C-protease inhibitor thysanone
    Bachu, Prabhakar
    Sperry, Jonathan
    Brimble, Margaret A.
    [J]. TETRAHEDRON, 2008, 64 (21) : 4827 - 4834
  • [2] EXTENSION OF THE NENITZESCU REACTION TO A CYCLIC ENAMINO KETONE - ONE-STEP SYNTHESIS OF 6-HYDROXY-9H-PYRIMIDO[4,5-B]INDOLE-2,4-DIONE
    BERNIER, JL
    HENICHART, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (21) : 4197 - 4198
  • [3] Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones
    Bonanni, Marco
    Marradi, Marco
    Cardona, Francesca
    Cicchi, Stefano
    Goti, Andrea
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2007, 3
  • [4] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [5] More Sustainable Approaches for the Synthesis of N-Based Heterocycles
    Candeias, Nuno R.
    Branco, Luis C.
    Gois, Pedro M. P.
    Afonso, Carlos A. M.
    Trindade, Alexandre F.
    [J]. CHEMICAL REVIEWS, 2009, 109 (06) : 2703 - 2802
  • [6] Sol-gel chemistry in medicinal science
    Coradin, T
    Boissière, M
    Livage, J
    [J]. CURRENT MEDICINAL CHEMISTRY, 2006, 13 (01) : 99 - 108
  • [7] d'Ischia M., 2008, COMPREHENSIVE HETERO, V3
  • [8] From Nature to Drug Discovery: The Indole Scaffold as a 'Privileged Structure'
    de Sa Alves, Fernando Rodrigues
    Barreiro, Eliezer J.
    Manssour Fraga, Carlos Alberto
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2009, 9 (07) : 782 - 793
  • [9] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
    Deiters, A
    Martin, SF
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
  • [10] Privileged structures: Applications in drug discovery
    DeSimone, RW
    Currie, KS
    Mitchell, SA
    Darrow, JW
    Pippin, DA
    [J]. COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2004, 7 (05) : 473 - 493