Indium-mediated allylation and propargylation of isatins: A facile synthesis of 3-substituted 3-hydroxyoxindoles

被引:29
作者
Nair, V [1 ]
Ros, S [1 ]
Jayan, CN [1 ]
Viji, S [1 ]
机构
[1] CSIR, Reg Res Lab, Div Organ Chem, Trivandrum 695019, Kerala, India
来源
SYNTHESIS-STUTTGART | 2003年 / 16期
关键词
indium; allylations; propargylation; isatins; oxindoles;
D O I
10.1055/s-2003-42428
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isatins undergo efficient allylation/propargylation when reacted with allyl/propargyl bromide in the presence of indium and sodium iodide to afford the corresponding 3-substituted 3-hydroxy-oxindoles.
引用
收藏
页码:2542 / 2546
页数:5
相关论文
共 18 条
  • [1] [Anonymous], 1994, CONTEMP ORG SYNTH
  • [2] PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS
    ARAKI, S
    SHIMIZU, T
    JOHAR, PS
    JIN, SJ
    BUTSUGAN, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) : 2538 - 2542
  • [3] ARAKI S, 1988, J ORG CHEM, V53, P1833
  • [4] Cinnolines. VII. The Neber-Bossel Synthesis
    Baumgarten, Henry E.
    Creger, Paul L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (17) : 4634 - 4638
  • [5] CINTAS P, 1995, SYNLETT, P1087
  • [6] The chemistry of isatins: a review from 1975 to 1999
    da Silva, JFM
    Garden, SJ
    Pinto, AC
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (03) : 273 - 324
  • [7] ELLIS GP, 1992, CHEM HETEROCYCLIC 2, V47
  • [8] A convenient methodology for the N-alkylation of isatin compounds
    Garden, SJ
    Torres, JC
    da Silva, LE
    Pinto, AC
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (09) : 1679 - 1689
  • [9] Organic syntheses using indium-mediated and catalyzed reactions in aqueous media
    Li, CJ
    Chan, TH
    [J]. TETRAHEDRON, 1999, 55 (37) : 11149 - 11176
  • [10] López-Alvarado P, 2002, SYNTHESIS-STUTTGART, P104