Reaktion von 3‐(Dimethylamino)‐2H‐azirinen mit 1,3‐Thiazolidin‐2‐thion

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Abstract
Reaction of 3‐(Dimethylamino)‐2H‐azirines with 1,3‐Thiazolidine‐2‐thioneReaction of 3‐(dimethylamino)‐2H‐azirines 1 and 1,3‐thiazolidine‐2‐thione (6) in MeCN at room temperature leads to a mixture of perhydroimidazo[4,3‐b]thiazole‐5‐thiones 7 and N‐[1‐(4,5‐dihydro‐1,3‐thiazol‐2‐yl)alkyl]‐N′,N′‐dimethylthioureas 8 (Scheme 2), whereas, in i‐PrOH at ca. 60°, 8 is the only product (Scheme 4). It has been shown that, in polar solvents or under Me2NH catalysis, the primarily formed 7 isomerizes to 8 (Scheme 4). The hydrolysis of 7 and 8 leads to the same 2‐thiohydantoine 9 (Scheme 3 and 5). The structure of 7a, 8c, and 9b has been established by X‐ray crystallography (Chapt. 4). Reaction mechanisms for the formation and the hydrolysis of 7 and 8 are suggested.

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