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Reactions of acetylthioacetanilide with arylamines in acetic acid in the presence of sodium acetate give 3-arylaminothiocrotonanilides in good yields. When treated with ω-bromoacetophenone in acetone, these products are converted to substituted 4-hydroxy-Δ2-thiazolinium bromides, one of which was dehydrated to obtain the corresponding thiazolium bromide. The structure of the heterocyclization products was confirmed by single crystal X-ray diffraction and NMR study of 2-acetonylidene-3,4-diphenyl-2,3-dihydrothiazole formed by dehydration of the corresponding Δ2-thiazolinium salt with simultaneous hydrolysis. |
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