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

Ametamey Simon M. | Zendy; Heimgartner Heinz | Zendy

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

Author(s) -

Ametamey Simon M.,

Heimgartner Heinz

Publication year - 1990

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19900730307

Subject(s) - chemistry , cyclopentane , oxazole , oxazolidine , medicinal chemistry , hydrolysis , sulfur , organic chemistry , polymer chemistry

Reaction of 3‐(Dimethylamino)‐2 H ‐azirines with 1,3‐Oxazolidine‐2‐thione to 3‐(2‐Hydroxyethyl)‐2‐ thiohydantoins The reaction of 3‐(dimethylamino)‐2 H ‐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′a H )‐imidazo [4, 3‐ b ] oxazole] ‐5′‐thione 8c . The mechanism is discussed.

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