666737-83-3Relevant academic research and scientific papers
Regiospecific synthesis of neuroprotective 1,4-benzoxazine derivatives through a tandem oxidation-Diels-Alder reaction
Nguyen, Khac Minh Huy,Schwendimann, Leslie,Gressens, Pierre,Largeron, Martine
, p. 3749 - 3756 (2015)
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.
Simultaneously Electrogenerated Cycloaddition Partners for Regiospecific Inverse-Electron-Demand Diels-Alder Reactions: A Route for Polyfunctionalized 1,4-Benzoxazine Derivatives
Blattes, Estelle,Fleury, Maurice-Bernard,Largeron, Martine
, p. 882 - 890 (2007/10/03)
A multistep one-pot electrochemical synthesis of a variety of complex 2-alkylamino-1,4-benzoxazine derivatives is described. The reactions are regiospecific and diastereospecific in the case of heterocyclic annulation. This cascade sequence, wherein both cycloaddition partners are generated in situ, at room temperature, under metal-free conditions, allows the inverse-electron-demand Diels-Alder reaction of an o-iminoquinone diene and a secondary alkylenamine dienophile, two chemically nonaccessible unstable entities. To increase the molecular diversity, a variant in which the enamine is separately prepared completes the aforementioned procedure. The extension of this reaction should be useful to generate libraries of heterocycles.
