title: Regiospecific synthesis of neuroprotective 1,4-benzoxazine derivatives through a tandem oxidation-Diels-Alder reaction.
abstract: The tandem oxidation-inverse electron demand Diels-Alder reaction of o-aminophenol derivatives and enamines has been accomplished at room temperature using a stoichiometric amount of manganese dioxide as the oxidant to furnish highly substituted 1,4-benzoxazine cycloadducts with complete regiochemical control. Because of its efficiency in introducing diverse elements in both cycloaddition partners, this one-pot process should allow the assembly of libraries of biologically relevant 1,4-benzoxazine derivatives. In this respect, the 3,3-diphenyl-substituted-1,4-benzoxazine derivative 3n was found to be a potent neuroprotective agent in an animal model of excitotoxic lesions in newborn mice.
authors: UMR 8638 CNRS-Université Paris Descartes, Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 avenue de l'Observatoire, 75270 Paris cedex 06, France. martine.largeron@parisdescartes.fr.
authors: Khac Minh Huy
authors: KM
authors: Nguyen
authors: Leslie
authors: L
authors: Schwendimann
authors: Pierre
authors: P
authors: Gressens
authors: Martine
authors: M
authors: Largeron
mesh_terms: D000818:Animals; D000831:Animals, Newborn; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D061565:Cycloaddition Reaction; D051379:Mice; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D048588:Benzoxazines; D018696:Neuroprotective Agents