Some 2-nitrothiazoles

Abstract
2-Nitrothiazole-5-carbaldehyde oxime (1) is dehydrated by trifluoroacetic anhydride or by phosgene and propene oxide to give the nitrile (2), which has been converted into 3-(2-nitrothiazol-5-yl)-1,2,4-oxadiazole (4). The oxime (1) is converted by acetic anhydride into 2-acetoxythiazole-5-carbonitrile (5) and by thionyl chloride into 2-chlorothiazole-5-carbonitrile (6). 3-(2-Aminothiazol-5-yl)-1,2,4-oxadiazole (7) reacts with nitrous acid in the presence of copper to give the nitro-compound (4), together with the deaminated compound 3-(thiazol-5-yl)-1,2,4-oxadiazole (8). Some similar deaminations have been observed.

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