An unambiguous synthesis of the published structure for the natural product sinharine (1) showed that the assignment was incorrect. (E)-3-( Methylthio )-N-(2-phenylethyl) propenamide (4) was proposed as an alternative structure and this was confirmed by synthesis. Similarly the literature proposal for the structure of methylsinharine was reviewed and the natural product tentatively reassigned as (E)-N-methyl-3-( methylthio )-N-(2-phenylethyl) propenamide.
Several derivatives of the novel 1,4,2-oxathiazin-6(5H)-one system were prepared by reaction of mercapto carboxylic acids with substituted carbohydroximoyl chlorides and subsequent cyclization of the resulting oxime acid with dicyclohexylcarbodiimide . The stability of the 1,4,2-oxathiazin-6(5H)-one system to acid and base conditions as well as to various nucleophiles was investigated.
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