Abstract
Thiobenzoyl isocyanate adds to 2-thiazoline and its 2-methyl derivative to afford the corresponding (4 + 2) cycloadducts. Reaction of benzoyl isocyanate with 2-methylthiazoline gives 2,3-dihydro-5-phenyl-8-benzoylcarbamoylthiazolo[3,2-c]pyrimidin-7-one. Thiobenzoyl isocyanate reacts with 2-methyl-2-thiazoline and -2-oxazoline at 90° to form the corresponding 8-thiobenzoylcarbamoylthiazolo- and -oxazolo[3,2-c]pyrimidin-7-ones, while reaction of benzoyl isocyanate with 2-methyloxazoline affords a 2:1 adduct, which with acetic acid gives the corresponding oxazolo[3,2-c]pyrimidine. Benzoyl isocyanate reacts with 2-ethyl-2-thiazoline to afford 2,3-dihydro-6-benzoyl-8-methylthiazolo[3,2-c]pyrimidine-5,7-dione and 2,3-dihydro-5-phenyl-8-methylthiazolo[3,2-c]pyrimidin-7-one; their acid and alkaline hydrolyses are described. Formation of these products is shown to proceed via attack of both isocyanates on the β-carbon of the tautomeric enamines of 2-alkyl-2-thiazoline and -2-oxazoline.
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