Issue 14, 2017
From the journal:

Organic & Biomolecular Chemistry

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

Hasan Mtiraoui,‡a   Kevin Renault,‡b   Morgane Sanselme,cd   Moncef Msaddek,*a   Pierre-Yves Renardb  and  Cyrille Sabot ORCID logo *b  

* Corresponding authors

a Université Monastir, Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/CHPNR, Department of Chemistry, Faculty of Science of Monastir, 5000 Monastir, Tunisia

b Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France
E-mail: cyrille.sabot@univ-rouen.fr

c Normandie Univ, France

d UNIROUEN, Laboratoire SMS EA3233, 1 rue Tesniere, France, F-76821 Mont Saint Aignan, France

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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DOI
https://doi.org/10.1039/C7OB00205J
Article type
Paper
Submitted
25 Jan 2017
Accepted
12 Mar 2017
First published
13 Mar 2017

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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