Sequential ring-opening of trans-1,4-cyclohexadiene dioxide for an expedient modular approach to 6,7-disubstituted (±)-hexahydro-benzo[1,4]oxazin-3-ones

Abstract

A modular approach to novel 6-amino-7-hydroxysubstituted hexahydro-benzo[1,4]oxazin-3-ones has been developed. The method involves a sequential ring-opening of trans-1,4-cyclohexadiene dioxide with amino nucleophiles. The resultant mono-epoxide from benzylamine was converted to a general electrophilic precursor, which enables the parallel treatment with amino nucleophiles to obtain a series of cyclohexane-fused morpholin-3-ones.