Preparation of selenyl 1,3-oxazines via PhICl2/Cu2O-promoted aminoselenation of O-homoallyl benzimidates with diselenides.

A practical electrophilic aminoselenation of O-homoallyl benzimidate with diselenides promoted by PhICl2/Cu2O has been developed. The easily available and stable diselenides were used as selenium sources. Various selenyl 1,3-oxazines, which are important frameworks in medicinal and biological chemistry, were easily obtained in moderate to good yields for the first time. Easy scaleup and scalability make this method attractive for the preparation of other valuable organoselenides.

Copper-Catalyzed Aminosulfonylation of O-Homoallyl Benzimidates with Sodium Sulfinates to Access Sulfonylated 1,3-Oxazines.

A facile copper-catalyzed aminosulfonylation of O-homoallyl benzimidates with sodium sulfinates in the presence of tert-butyl peroxybenzoate (TBPB) and XPhos ligand has been developed. By using this protocol, a variety of potentially bioactive 1,3-oxazines were directly synthesized. This method has the merits of a cheap catalyst, easily available and stable sulfone reagents, and simple operation.