有机催化靛红与4-苯基-3-丁炔-2-酮高效合成3-取代-3-羟基氧化吲哚类衍生物

Organocatalytic efficient synthesis of 3-substituted-3-hydroxy-indolin-2-one derivatives from isatins and 4-phenylbut-3-yn-2-one

发展了一种有机催化靛红与4-苯基-3-丁炔-2-酮的反应,提供了高效合成3-取代-3-羟基氧化吲哚类衍生物的方法.该方法所采用的有机催化剂廉价易得,靛红底物中氮原子无需保护,反应操作简单,条件温和,各种不同取代基的靛红以及4-芳基-3-丁炔-2-酮都能较好地参与反应且以较高的收率合成目标产物.另外,该体系也可用于催化靛红与3-己炔-2-酮的反应.

An organocatalytic Aldol reaction between isatins and 4-phenylbut-3-yn-2-one was developed, which offers an efficient access to 3-substituted-3-hydroxy indolin-2-one skeletons. The present methodology has the advantages of low-cost organocatalyst, mild reaction conditions, and simple operation. In the presence of Et3N, a series of substituted isatins reacted with 4-phenylbut-3-yn-2-one smoothly to furnish desired products in 83-99% yields. Hex-3-yn-2-one could also be employed in the reaction to afford 3-substituted-3-hydroxyindolin-2-one derivative in high yield.