A new and versatile one-pot synthesis of indol-2-ones by a novel Ugi-four-component-Heck reaction

被引:69
作者
Umkehrer, M [1 ]
Kalinski, C [1 ]
Kolb, E [1 ]
Burdack, C [1 ]
机构
[1] Priaton GmbH, Tutzing, Germany
关键词
D O I
10.1016/j.tetlet.2006.01.149
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel one-pot-synthesis of highly substituted indol-2-ones using a combination of Ugi and Fleck reaction (U-4CR-Heck) is described. The synthesized indol-2-ones represent an interesting pharmacological scaffold with Four potential points of diversity. Thus, this novel reaction-type is amenable to combinatorial high-throughput screening. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2391 / 2393
页数:3
相关论文
共 29 条
  • [1] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions
    Amatore, C
    Jutand, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) : 314 - 321
  • [2] Substituted E-3-(2-chloro-3-indolylmethylene)1, 3-dihydroindol-2-ones with antitumor activity
    Andreani, A
    Granaiola, M
    Leoni, A
    Locatelli, A
    Morigi, R
    Rambaldi, M
    Garaliene, V
    Farruggia, G
    Masotti, L
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (05) : 1121 - 1128
  • [3] Synthesis and antitumor activity of 1,5,6-substituted E-3-(2-chloro-3-indolylmethylene)-1,3-dihydroindol-2-ones
    Andreani, A
    Granaiola, M
    Leoni, A
    Locatelli, A
    Morigi, R
    Rambaldi, M
    Garaliene, V
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (12) : 2666 - 2669
  • [4] Short and diverse route toward complex natural product-like macrocycles
    Beck, B
    Larbig, G
    Mejat, B
    Magnin-Lachaux, M
    Picard, A
    Herdtweck, E
    Dömling, A
    [J]. ORGANIC LETTERS, 2003, 5 (07) : 1047 - 1050
  • [5] A novel three-component butenolide synthesis
    Beck, B
    Magnin-Lachaux, M
    Herdtweck, E
    Dömling, A
    [J]. ORGANIC LETTERS, 2001, 3 (18) : 2875 - 2878
  • [6] Recent developments in isocyanide based multicomponent reactions in applied chemistry
    Dömling, A
    [J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
  • [7] Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1
  • [8] Domling A., 2000, ANGEW CHEM, V112, P3300
  • [9] The asymmetric intramolecular Heck reaction in natural product total synthesis
    Dounay, AB
    Overman, LE
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2945 - 2963
  • [10] Sequential Ugi/Heck cyclization strategies for the facile construction of highly functionalized N-heterocyclic scaffolds
    Gracias, V
    Moore, JD
    Djuric, SW
    [J]. TETRAHEDRON LETTERS, 2004, 45 (02) : 417 - 420