Issue 12, 2015

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
09 Jan 2015
Accepted
03 Feb 2015
First published
03 Feb 2015

Org. Biomol. Chem., 2015,13, 3749-3756

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

K. M. H. Nguyen, L. Schwendimann, P. Gressens and M. Largeron, Org. Biomol. Chem., 2015, 13, 3749 DOI: 10.1039/C5OB00049A

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