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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2015

Regiospecific synthesis of neuroprotective 1,4-benzoxazine derivatives through a tandem oxidation–Diels–Alder reaction

Résumé

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 for introducing diversity elements in both cycloadditions partners, this one-pot process should allow the assembly of libraries of biologically relevant 1,4- benzoxazine derivatives. In this respect, 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.
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hal-02384706 , version 1 (21-11-2020)

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Khac Minh Huy Nguyen, Leslie Schwendimann, Pierre Gressens, Martine Largeron. Regiospecific synthesis of neuroprotective 1,4-benzoxazine derivatives through a tandem oxidation–Diels–Alder reaction. Organic & Biomolecular Chemistry, 2015, 13 (12), pp.3749-3756. ⟨10.1039/c5ob00049a⟩. ⟨hal-02384706⟩
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