Substituent-Controlled Selective Synthesis of Spirooxindoles and Oxazolyloxindoles via Two Tandem Reactions
Substituent-Controlled Selective Synthesis of Spirooxindoles and Oxazolyloxindoles via Two Tandem Reactions
复制标题
通过两个串联反应取代基控制选择性合成螺吲哚和恶唑吲哚
DOI：
10.1002/ajoc.201500290
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发表时间：
2016
影响因子：
2.7
通讯作者：
Li Ying
中科院分区：
文献类型：
--
作者：
Liu Yun;Xue Jijun;Sun Zhou;Liu Dongxue;Xing Yacheng;Li Ying
本文介绍了一种由相似原料在温和条件下通过两步串联反应制备各种氧化吲哚衍生物的方法。氧化吲哚衍生物是广泛存在于天然产物和药物中的重要生物活性核心。本文采用取代基控制的产物选择性策略，成功地从亚甲基吲哚啉酮和溴代酰胺合成了具有优良非对映选择性的螺羟吲哚和恶唑基羟吲哚。该合成具有明确的化学选择性，这依赖于不同的取代基的-溴酰胺的氮原子。从机理上分析，以N-苄氧基-溴代酰胺为原料，通过消除-Michael-Michael加成得到螺羟基吲哚，以N-苯甲酰基-溴代酰胺为原料，通过环化-Michael加成得到恶唑基羟基吲哚，这两种方法巧妙地将亲核组分的形成和亲核引发的级联反应一锅完成.
A common synthetic method involving two tandem processes to prepare varieties of oxindole derivatives, which are important bioactive cores that exist widely in natural products and drugs, from similar materials under mild conditions is described. Herein a substituent-controlled product-selective strategy succeeded in synthesizing spirooxindoles and oxazolyloxindoles with excellent diastereoselectivity from methyleneindolinones and -bromoamides. The synthesis has clear chemoselectivity, which relies on different substituent groups at the nitrogen atoms of -bromoamides. From mechanism analysis, the spirooxindoles were constructed via elimination-Michael-Michael addition from N-benzyloxy--bromoamides, while oxazolyloxindoles were achieved via cyclization-Michael addition from N-benzoyl--bromoamides, both of which cleverly combined the nucleophilic component formation and nucleophile-triggered cascade reactions in one pot.