期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 8, 页码 3198-3204出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo050130w
关键词
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Reactions of 2,3-indolinediones (isatins) with stabilized organometallic reagents were investigated in aqueous media. Isatins and a variety of stabilized organic halides undergo coupling under Barbier-type conditions in the presence of different metals (indium, tin, zinc) and additives (ammonium chloride, hydrobromic acid, bismuth(III) chloride, hafnium(IV) chloride). The regiochemistry of the processes (carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions) were generally excellent. On this basis, simple and fast protocols for the Synthesis of the potentially bioactive 3-substituted 3-hydroxyoxindole moiety were developed.
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