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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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Publication details

The article was received on 16 Jun 2017, accepted on 21 Aug 2017 and first published on 23 Aug 2017


Article type: Communication
DOI: 10.1039/C7GC01783A
Citation: Green Chem., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7GC01783A

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