Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones

A novel and practical synthesis of 3-benzoylquinoxalin-2(1H)-ones from benzodiazepin-2-ones in two steps from commercially available starting materials is reported. The reaction was achieved in the presence of N-bromosuccinimide in DMSO which served both as a solvent and an oxidant. Significantly, t...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (14), p.3060-3068
Main Authors: Mtiraoui, Hasan, Renault, Kevin, Sanselme, Morgane, Msaddek, Moncef, Renard, Pierre-Yves, Sabot, Cyrille
Format: Article
Language:English
Subjects:
Benzodiazepinones - chemistry
Chemical Sciences
Dimethyl Sulfoxide - chemistry
Organic chemistry
Oxidation-Reduction
Quinoxalines - chemistry
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Summary:A novel and practical synthesis of 3-benzoylquinoxalin-2(1H)-ones from benzodiazepin-2-ones in two steps from commercially available starting materials is reported. The reaction was achieved in the presence of N-bromosuccinimide in DMSO which served both as a solvent and an oxidant. Significantly, the yet unknown ketone to alcohol fluorescence turn-on of benzoylquinoxalinones was unveiled through the preparation of a fluorescently labelled cholesterol conjugate.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00205j