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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