Umsetzung von 3‐(Dimethylamino)‐2H‐azirinen mit 1,3‐Oxazolidin‐2‐thion zu 3‐(2‐Hydroxyethyl)‐2‐thiohydantoinen
- 2 May 1990
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 73 (3) , 594-598
- https://doi.org/10.1002/hlca.19900730307
Abstract
Reaction of 3‐(Dimethylamino)‐2H‐azirines with 1,3‐Oxazolidine‐2‐thione to 3‐(2‐Hydroxyethyl)‐2‐ thiohydantoinsThe 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.Keywords
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