Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 12, Pages 3749-3756Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob00049a
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- CNRS
- Inserm
- Paris Descartes University
- Paris Diderot University
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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.
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