Metal-free base-mediated oxidative annulation cascades to 3-substituted-3-hydroxyoxindole and its 3-spirocyclic derivative,Green Chemistry

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Metal-free base-mediated oxidative annulation cascades to 3-substituted-3-hydroxyoxindole and its 3-spirocyclic derivative
Green Chemistry ( IF 9.3 ) Pub Date : 2017-08-23 00:00:00 , DOI: 10.1039/c7gc01783a
Min Liu _{1,

2,

3,

4} , Chunxia Zhang _{1,

2,

3,

4} , Mingruo Ding _{1,

2,

3,

4} , Bencan Tang _{4,

5,

6,

7,

8} , Fengzhi Zhang _{1,

2,

3,

4}

Affiliation

A simple and efficient method was developed for the construction of the medicinally important 3-substituted-3-hydroxyoxindole and its 3-spirocyclic derivatives with readily available aniline derivatives as starting materials. This highly atom- and step-economical one-pot protocol was carried out under metal-free base-mediated conditions through a novel oxidative annulation strategy with oxygen as the oxidant. The key intermediates were isolated and confirmed. A reasonable reaction pathway was proposed and supported by the preliminary experiments, and the computational studies were carried out to understand the energetics of the key rearrangement reaction.

中文翻译：

无金属的碱介导的氧化环化反应级联成3-取代的3-羟基羟吲哚及其3-螺环衍生物

开发了一种简单有效的方法，以易于获得的苯胺衍生物为原料，构建具有医学上重要意义的3-取代-3-羟基羟吲哚及其3-螺环衍生物。通过使用氧作为氧化剂的新型氧化环化策略，在无金属碱介导的条件下进行了这种高度原子和步骤经济的一锅操作方案。分离并确认了关键中间体。初步的实验提出并支持了合理的反应途径，并进行了计算研究以了解关键重排反应的能量学。

更新日期：2017-09-04

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