Dérivés de l'imidazo[2,l-b]thiazole. IX. Comportement du phénacyl-3 dihydro-5,6 imidazo[2,1-b]thiazole et du phénacylidène-3 tétrahydro-2,3,5,6 imidazo[2,1-b]thiazole vis-à-vis du chlorhydrate d'hydroxylamine

The reaction of hydoxylamine hydrochloride with two imidazothiazoles, having a ketonic carbonnyl group, leads to two types of compounds according to the quantity of the sodium acetate used. 3-Phenacyl-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride gives logically the corresponding oxime, isolated in salt form or as a base depending upon the quantity of sodium acetate added. Furbase depending upon the quantity of sodium acetate added. Furthermore, a systematic allylic rearrangement was observed with migration of thiazole double bond to the adjacent nuclear position. 3-Phenacylidene-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole gave directly in the absence of sodium acetate, a rearranged oxime salt. On the other hand, in the presence of sodium acetate, we obtained a hgydroxylamine which was characterized by a double bond in the 2,3-position of the thiazole ring. It is noteworthy that no transformation of the hydroxylamine into the oxime or vice-versa occurs whatever the pH of the solution. These different compounds have no fungistatic activity in contrast to the corresponding ketones.