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Reaktion von 3‐(Dimethylamino)‐2 H ‐azirinen mit 1,3‐Thiazolidin‐2‐thion
Author(s) -
Ametamey Simon M.,
Prewo Roland,
Bieri Jost H.,
Heimgartner Heinz,
Obrecht Jean Pierre
Publication year - 1986
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.19860690825
Subject(s) - chemistry , thiazolidine , thiazole , medicinal chemistry , hydrolysis , alkyl , catalysis , stereochemistry , organic chemistry
Reaction of 3‐(Dimethylamino)‐2 H ‐azirines with 1,3‐Thiazolidine‐2‐thione Reaction of 3‐(dimethylamino)‐2 H ‐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 Me 2 NH 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.