Umsetzung von 3-(Dimethylamino)-2H-azirinen mit 1,3-Oxazolidin-2-thion zu 3-(2-Hydroxyethyl)-2-thiohydantoinen

Reaction of 3-(Dimethylamino)-2H-azirines with 1,3-Oxazolidine-2-thione to 3-(2-Hydroxyethyl)-2- thiohydantoins The reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-oxazolidine-2-thione (6), in MeCN at room temperature, yields, after hydrolytic workup, 3-(2-hydroxyethyl)-2-thiohydantoins 7 (Scheme 2). In the case of the spirocyclic 1c, crystallization of the crude reaction mixture leads to spiro [cyclopentane-1, 7′(7′aH)-imidazo [4, 3-b] oxazole] -5′-thione 8c. The mechanism is discussed.