This work represents the first example of a gold-catalyzed
formation
of 1,3-thiazine/1,3-thiazinane by means of a catalytic approach and
further uncommon isolation of the two tautomers. The developed protocol
gives rise to a broad scope of 1,3-thiazine derivatives with excellent
yields in short reaction times. Interestingly, different isomers could
be obtained depending on the state of the compound, and in the crystal
state the 1,3-thiazinane isomer is obtained, while in solution the
1,3-thiazine is the unique isomer. This work represents an interesting
approach for the synthesis of potential biologically relevant molecules
and a crucial precedent in tautomerism isolation and characterization.