Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones

被引：163
作者：
Alfonsi, M [1 ]
Arcadi, A [1 ]
Aschi, M [1 ]
Bianchi, G [1 ]
Marinelli, F [1 ]
机构：
[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, Fac Sci, I-67010 Capitol, AQ, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 06期
关键词：
D O I：
10.1021/jo047793i
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The gold-catalyzed reaction of 2-alkynyl-phenylamines with alpha,beta-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/alpha,beta-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140 degrees C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.
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收藏
页码：2265 / 2273
页数：9
相关论文
共 123 条
  • [1] Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines
    Abbiati, G
    Arcadi, A
    Bianchi, G
    Di Giuseppe, S
    Marinelli, F
    Rossi, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 6959 - 6966
  • [2] A simple, two-step synthesis of 3-iodoindoles
    Amjad, M
    Knight, DW
    [J]. TETRAHEDRON LETTERS, 2004, 45 (03) : 539 - 541
  • [3] Recent applications of gold catalysis in organic synthesis
    Arcadi, A
    Di Giuseppe, S
    [J]. CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) : 795 - 812
  • [4] Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles
    Arcadi, A
    Bianchi, G
    Di Giuseppe, S
    Marinelli, F
    [J]. GREEN CHEMISTRY, 2003, 5 (01) : 64 - 67
  • [5] Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO
  • [6] 2-R
  • [7] Conversion of homochiral amines and α-amino esters to their chiral 1,2,3,5-substituted pyrrole derivatives via gold-catalysed amination/annulation reactions of 2-propynyl-1,3-dicarbonyl compounds
    Arcadi, A
    Di Giuseppe, S
    Marinelli, F
    Rossi, E
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (19) : 2715 - 2720
  • [8] Sequential alkylation/transition metal catalysed annulation reactions of 1,3-dicarbonyl compounds with propargyl bromide
    Arcadi, A
    Cerichelli, G
    Chiarini, M
    Di Giuseppe, S
    Marinelli, F
    [J]. TETRAHEDRON LETTERS, 2000, 41 (47) : 9195 - 9198
  • [9] Gold-catalyzed conjugate addition type reaction of indoles with α,β-enones
    Arcadi, A
    Bianchi, G
    Chiarini, M
    D'anniballe, G
    Marinelli, F
    [J]. SYNLETT, 2004, (06) : 944 - 950
  • [10] Arcadi A, 2000, SYNLETT, P647
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