Reaction of unsaturated azlactones with sulfur nucleophiles: some observations

Abstract
Unsaturated azlactones undergo thiolysis with toluene-α-thiol, but 2-substituted (Z)-4-o-acetoxybenzylidene-4,5-dihydrooxazol-5-ones form 3-acylaminocoumarins in the presence of triethylamine. Sodium sulfide in ethanol brings about ethanolysis of the 1,5 bond and deacetylation of an acetoxy group. (Z)-4-Benzylidene-4,5-dihydrooxazol-5-one reacts with potassium thiocyanate to give (E)-4(5)-benzylidene-2-thiohydantoin.

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