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Paper | Regular issue | Vol 89, No. 8, 2014, pp.1827-1843
Published online, 3rd July, 2014
DOI: 10.3987/COM-14-13020
Synthesis of Novel Thiazole and 1,3,4-Thiadiazole Derivatives Incorporating Phenylsulfonyl Moiety

Ahmed E. M. Mekky, Ahmed F. Darweesh, Amani A. Salman, and Ahmad M. Farag*

*Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Abstract

Reaction of 1-(benzothiazol-2-yl)-2-phenylsulfonyl-1-ethanone (1) and 1-(1-methyl-1H-benzimidazol-2-yl)-2-(phenylsulfonyl)-1-ethanone (2) with phenyl isothiocyanate afforded the corresponding potassium salts 3 and 4, respectively. The potassium salts 3 and 4 were converted into the corresponding (Z)-1-(benzothiazol-2-yl)-3-mercapto-3-(phenylamino)-2-(phenylsulfonyl) propenone (5) and (Z)-1-(1-methylbenzimidazole-2-yl)-3-mercapto-3-(phenylamino)-2-(phenylsulfonyl)propenone (6), respectively upon acidification with HCl. The latter products were used as versatile building blocks for novel 1,3,4-thiadiazole derivatives via their reactions with the appropriate hydrazonyl halides. They have been also utilized for the synthesis of thiazole ring systems incorporating phenylsulfonyl moiety.