Rearrangements of the aminoalkylation products of tetrahydro-2H-1,3-oxazine-2-thione

The nature of the compounds afforded by the rearrangement of the aminopropylation and aminoethylation products of tetrahydro-2H-1,3-oxazine-2-thione (I) has been investigated. In both instances compounds that can be considered to result from ring opening at either the C-O or C-S bond of a hypothetical bicyclic intermediate of structure IV were obtained. The compounds required for identification of the rearrangement products have been prepared by the reaction of the 2-methylthio derivatives of 2-thiazoline, 5,6-dihydro-4H-1,3-thiazine, and 5,6-dihydro-4H-1,3-oxazine with the appropriate hydroxyalkylamine or mercaptoalkylamine.