Synthesis and mass spectral fragmentation patterns of some thiazole and 2-thioxo-imidazolidin-4-one derivatives

ABSTRACT

2-[[5-ARYL-THIAZOL-2-YL]-hydrazonomethyl-phenols [2a, b] and 3-[[2-hydroxybenzylidiene]-amino]-2-thioxo-imidazolidin-4-one [3] were prepared via cyclization of salicylaldehydethiosemicarbazone [1] with omega [small latter]-bromomethyl aryl ketones and ethyl chloroacetate in presence of fused sodium acetate. Reaction of 3 with hydrazine hydrate, acetic anhydride, benzaldehyde, ethyl iodide, methyl acrylate and diazonium chloride yielded the corresponding salicylaldazine [4], 1-acetyl-3-[[2-acetoxybenzylidene]-amino]-2-thioxoimidazolidin-4-one [5], 3-[[2-hydroxybenzylidene]-amino]-5-benzylidene-2-thioxo-imidazolidin-4-one [6], 1-substituted-3-[[2-hydroxybenzylidene]-amino]-2-thioxo-imidazolidin-4-ones [8 and 9] and 3-[[5-phenylazo-2-hydroxybenzylidene]-amino]-2-thioxo-imidazolidin-l-one [10]. The mass spectral fragmentation patterns of the compounds are described