Stille couplings of 3-(trimethylstannyl)-5-bromo-2-pyrone for the syntheses of 3-aryl-5-bromo-2-pyrones and their ambident dienyl characters

被引:32
作者
Lee, JH
Kim, WS
Lee, YY
Cho, CG [1 ]
机构
[1] Hanyang Univ, Coll Nat Sci, Dept Chem, Seoul 133791, South Korea
[2] Hanyang Univ, Coll Nat Sci, Dept Internal Med, Seoul 133791, South Korea
关键词
D O I
10.1016/S0040-4039(02)01182-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-(Trimethylstannyl)-5-bromo-2-pyrone underwent facile Stille Coupling reactions with aryl halides to produce various 3-substituted 5-bromo-2-pyrones. The resulting 3-aryl-2-pyrone derivatives underwent both normal and inverse electron demand Diels Alder cycloadditions depending on the type of the dienophiles being reacted. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5779 / 5782
页数:4
相关论文
共 22 条
  • [1] Diels-Alder cycloaddition of 5-aryl-2-pyrones
    Afarinkia, K
    Berna-Canovas, J
    [J]. TETRAHEDRON LETTERS, 2000, 41 (25) : 4955 - 4958
  • [2] A novel route to 6-substituted and 5,6-disubstituted 2-pyrones
    Bellina, F
    Biagetti, M
    Carpita, A
    Rossi, R
    [J]. TETRAHEDRON LETTERS, 2001, 42 (15) : 2859 - 2863
  • [3] Bodwell GJ, 1999, SYNLETT, P477
  • [4] 3-aryl and 5-aryl-4-methoxy-6-methyl-2H-pyran-2-ones by Suzuki cross-coupling reactions of 3- and 5-halogeno-4-methoxy-6-methyl-2H-pyran-2-ones
    Cerezo, S
    Moreno-Mañas, M
    Pleixats, R
    [J]. TETRAHEDRON, 1998, 54 (27) : 7813 - 7818
  • [5] Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone with cycloalkenyl silyl ethers for the synthesis of bicarbocycles
    Cho, CG
    Kim, YW
    Kim, WK
    [J]. TETRAHEDRON LETTERS, 2001, 42 (46) : 8193 - 8195
  • [6] One step preparation of bromo-2-pyrones via bromo-decarboxylation of 2-pyrone-carboxylic acids
    Cho, CG
    Park, JS
    Jung, IH
    Lee, H
    [J]. TETRAHEDRON LETTERS, 2001, 42 (06) : 1065 - 1067
  • [7] An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling
    Cho, CS
    Kim, BT
    Kim, TJ
    Shim, SC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) : 9020 - 9022
  • [8] Application of the Pd-catalyzed heteroarylation to the synthesis of 5-(indol-2′-yl)pyridin-2-one and 5-(indol-2′-yl)pyran-2-one
    Danieli, B
    Lesma, G
    Martinelli, M
    Passarella, D
    Peretto, I
    Silvani, A
    [J]. TETRAHEDRON, 1998, 54 (46) : 14081 - 14088
  • [9] A convenient synthesis of 2H-pyran-2-ones and of 3-and 5-bromo-2H-pyran-2-ones
    Kotretsou, SI
    Georgiadis, MP
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2000, 32 (02) : 161 - 167
  • [10] Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes
    Larock, RC
    Doty, MJ
    Han, XJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) : 8770 - 8779