Alcaide Benito, Almendros Pedro, Rodríguez-Acebes Raquel
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain.
J Org Chem. 2005 Apr 15;70(8):3198-204. doi: 10.1021/jo050130w.
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.
在水性介质中研究了2,3-吲哚二酮（异吲哚酮）与稳定化有机金属试剂的反应。异吲哚酮和多种稳定化有机卤化物在不同金属（铟、锡、锌）和添加剂（氯化铵、氢溴酸、氯化铋(III)、氯化铪(IV)）存在下，于巴比耶型条件下发生偶联反应。这些反应（羰基烯丙基化、溴代烯丙基化、1,3-丁二烯-2-基化、炔丙基化或联烯基化反应）的区域化学通常表现出色。在此基础上，开发了用于合成具有潜在生物活性的3-取代-3-羟基氧化吲哚部分的简单快速方法。
