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, the yet unknown ketone to alcohol fluorescence turn-on of benzoylquinoxalinones was unveiled through the preparation of a fluorescently labelled cholesterol conjugate.
Université Monastir, Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/CHPNR, Department of Chemistry, Faculty of Science of Monastir, 5000 Monastir, Tunisia.
Hasan
H
Mtiraoui
Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France. cyrille.sabot@univ-rouen.fr.
Kevin
K
Renault
Normandie Univ, France and UNIROUEN, Laboratoire SMS EA3233, 1 rue Tesniere, France, F-76821 Mont Saint Aignan, France.
Morgane
M
Sanselme
Université Monastir, Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/CHPNR, Department of Chemistry, Faculty of Science of Monastir, 5000 Monastir, Tunisia.
Moncef
M
Msaddek
Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France. cyrille.sabot@univ-rouen.fr.
Pierre-Yves
PY
Renard
Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France. cyrille.sabot@univ-rouen.fr.
Cyrille
http://orcid.org/0000-0002-5014-7217
C
Sabot
D001570:Benzodiazepinones / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D010084:Oxidation-Reduction; D011810:Quinoxalines / Q000737:chemistry*
D001570:Benzodiazepinones; D011810:Quinoxalines; D004121:Dimethyl Sulfoxide