SYNTHESIS OF NOVEL THIAZOLE AND 1,3,4-THIADIAZOLE DERIVATIVES INCORPORATING PHENYLSULFONYL MOIETY

摘要

Reaction of l-(benzothiazol-2-yl)-2-phenylsulfonyl-l-ethanone (1) and l-(l-methyl-li/-benzimidazol-2-yl)-2-(phenylsulfonyl)-l-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)-l-(benzothiazol-2-yl)-3-mercapto-3-(phenylamino)-2-(phenylsulfonyl) propenone (5) and (Z)-l-(l-methylbenzimidazole-2-yl)-3-mercapto-3-(phenylamino)-2-(phenylsulfonyl)propenone (6), respectively upon acidification with HC1. 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.