Abstract
Substitution by H 2O in the presence of HCl and by NH(CH 3) 2 occurs at position 2 of 5-acetyl-2-benzylthio-6H-1,3-thiazine without ring opening (in the first step for the amine). Substitution by the softer anion derived from diethylmalonate (and most likely HS −) occurs at position 6 with ring-opening. Subsequent cyclisations give the corresponding thiocarbonyl compounds. All these reactions are accompanied by elimination of the labile benzylthio group.
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