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Issue 19, 2017
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Metal-free base-mediated oxidative annulation cascades to 3-substituted-3-hydroxyoxindole and its 3-spirocyclic derivative

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Abstract

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.

Graphical abstract: Metal-free base-mediated oxidative annulation cascades to 3-substituted-3-hydroxyoxindole and its 3-spirocyclic derivative

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Supplementary files

Article information


Submitted
16 Jun 2017
Accepted
21 Aug 2017
First published
23 Aug 2017

Green Chem., 2017,19, 4509-4514
Article type
Communication

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

M. Liu, C. Zhang, M. Ding, B. Tang and F. Zhang, Green Chem., 2017, 19, 4509
DOI: 10.1039/C7GC01783A

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