Synthesis, Reactions and Stereochemistry of 3-Hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and Some Perhydrogenated Derivatives

Article abstract of DOI:10.1016/S0040-4020(01)81589-1

3-Hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and a number of its perhydrogenated derivatives were prepared from the corresponding 2-hydroxycarboxamides by treatment with a formaldehyde/formic acid mixture.Thermal decomposition of the 3-hydroxymethyl derivatives led to the previously unknown parent compounds.With one exception (14), both in the N-unsubstituted (16-18) and in the N-substituted (7-15) cyclopentane- and cyclohexane-fused derivatives the oxazinone ring predominantly attains a single half-chair conformation.