TEMPO-catalyzed electrochemical dehydrogenative cyclocondensation of o -aminophenols: synthesis of aminophenoxazinones as antiproliferative agents

The aminophenoxazinone core is widely prevalent in natural products, dyes and pharmaceutical molecules. We report here a TEMPO-catalyzed electrosynthetic method allowing the dehydrogenative cyclocondensation of o -aminophenols. This mild and sustainable method proceeds in the absence of stoichiometr...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2021-11, Vol.23 (21), p.8566-8570
Main Authors: Zhou, Jianmin, Ma, Zhi-Yuan, Shonhe, Chantale, Ji, Su-Hui, Cai, Yun-Rui
Format: Article
Language:English
Subjects:
Aminophenol
Dehydrogenation
Dimerization
Electrocatalysts
Electrochemistry
Green chemistry
Natural products
Oxidants
Oxidizing agents
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Summary:The aminophenoxazinone core is widely prevalent in natural products, dyes and pharmaceutical molecules. We report here a TEMPO-catalyzed electrosynthetic method allowing the dehydrogenative cyclocondensation of o -aminophenols. This mild and sustainable method proceeds in the absence of stoichiometric oxidants and uses an easily available organo-electrocatalyst to access pharmaceutically valuable 2-aminophenoxazinones. Mechanistic studies indicate that the electrochemically generated TEMPO + enables the oxidative radical homo-dimerization of o -aminophenols. The application of electrosynthesis provides an approach for the synthesis of pseudo-aminophenoxazinone alkaloids with improved structural diversification and bioactivities.
ISSN:1463-9262
1463-9270
DOI:10.1039/D1GC02908H