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Issue 14, 2017
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Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones

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Abstract

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.

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

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Publication details

The article was received on 25 Jan 2017, accepted on 12 Mar 2017 and first published on 13 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00205J
Citation: Org. Biomol. Chem., 2017,15, 3060-3068
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    Metal-free oxidative ring contraction of benzodiazepinones: an entry to quinoxalinones

    H. Mtiraoui, K. Renault, M. Sanselme, M. Msaddek, P. Renard and C. Sabot, Org. Biomol. Chem., 2017, 15, 3060
    DOI: 10.1039/C7OB00205J

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