S→N type Smiles rearrangement of the aminoethanethiol moiety attached to heterocyclic compounds

Base catalysed S→N type Smiles rearrangement of aminoethanethiol-substituted pyridine and triazine compounds led to formation of the corresponding thiol or disulfide compounds. Prior to rearrangement, the heteroaryl sulfanylethylamines could be prepared in high yields as the hydrochloride or trifluoroacetate salts from the corresponding tert-BOC protected amine.