Abstract
The Michael addition of 3-imino-1,4,2-dithiazoles to 4-arylidene-1,3-oxathiolan-5-one afforded isolable adducts regio- and diastereoselectively, which underwent mercaptoacetylative annulation of the mercaptopyrimidine ring onto the dithiazole under solvent-free microwave irradiation conditions. Alternatively, similar conjugate addition of [(methylsulfinyl)methyl]isothioureas to 4-arylidene-1,3-oxathiolan-5-one diastereoselectively afforded Michael adducts that underwent mercaptoacetylative ring transformation followed by heterocyclization via deoxygenative demethyl-ation with thionyl chloride to yield the same products, 7-aryl- or 2,7-diaryl-6,7-dihydro-6-mercapto-5 H-[1,4,2]dithiazolo[2,3- A]pyrimidin-5-ones, regio- and diastereoselectively.
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