Conversion of methylthiomethyleniminium salts into thioesters, esters, and amides

In this article, we report the unexpected formation of thioesters when methylthiomethyleniminium salts are treated with moist pyridine at room temperature (RT). While treatment of methylthiomethyleniminium salts with moist DMF at RT gave amides. Finally, they are refluxed in ethanol, esters are formed selectively in most of the cases and formation of a mixture of ester and amide is observed in few cases. The plausible mechanisms of formation of these unexpected products are also presented.