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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2017

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

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-02329806 , version 1 (23-10-2019)

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Citer

Hasan Mtiraoui, Kévin Renault, Morgane Sanselme, Moncef Msaddek, Pierre-Yves Renard, et al.. Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones. Organic & Biomolecular Chemistry, 2017, 15 (14), pp.3060-3068. ⟨10.1039/C7OB00205J⟩. ⟨hal-02329806⟩
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