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Ringöffnung von Nitrothiazolen
Author(s) -
Ilvespää Atso O.
Publication year - 1968
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.19680510729
Subject(s) - chemistry , thiazole , ring (chemistry) , steric effects , dimethyl sulfoxide , nitro , solvent , sulfoxide , medicinal chemistry , stereochemistry , organic chemistry , alkyl
The reaction between 2‐halogeno‐5‐nitro‐thiazoles and amines has been studied. Especially the sterically hindered strongly basic secondary aliphatic amines tend to cause opening of the thiazole ring system, resulting in the formation of the heretofore unknown (1‐nitro‐2‐amino‐vinyl)‐thiocyanates. The ring opening is favored by a highly polar solvent, such as dimethyl sulfoxide. A simple reaction mechanism is proposed and some properties of these new compounds are discussed.