Synthesis and structure confirmation of 2,4-disubstituted thiazole and 2,3,4-trisubstituted thiazole as thiazolium bromide salts

Abstract

Abstract: The synthesis of 4-substituted 2-(2-arylhydrazinyl)thiazol-3-ium bromides and 4-aryl-2-(substituted amino)-3-(phenylamino)thiazol-3-ium bromide derivatives in high yields from the interaction of mono- and di-substituted thiosemicarbazides with phenacyl bromide derivatives is reported. The synthesized products have been elucidated using various spectroscopic tools such as IR, NMR, and mass spectrometry. Also the structure of three of the obtained compounds have been confirmed using X-ray crystallographic analyses, which showed that compounds 2-[2-(2,4-dinitrophenyl)hydrazinyl]-4-phenylthiazol-3-ium bromide and 4-phenyl-2,3-bis(phenylamino)thiazol-3-ium bromide crystals have a monoclinic shape and belonged to space group P21/c, whereas the crystals of 4-phenyl-2-(2-tosylhydrazinyl)thiazol-3-ium bromide show an orthorhombic shape with the space group Pbca Graphic abstract: [Figure not available: see fulltext.]