Synthesis and antimicrobial activity of new 1,2,4-triazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, thiopyrane, thiazolidinone, and azepine derivatives

4-oxo-4-phenylbutanehydrazide3was reacted with aryl or alkyl isothiocyanates to give the correspondingN-substituted-2-(4-oxo-4-phenylbutanoyl) hydrazine-1-carbothioamide4a-c. Cyclization of thiosemicarbazides4a-cwith sodium hydroxide led to the formation of 3-(4-sub-5-thioxo-1,2,4-triazol-3-yl)-propanone5a-c. Desulfurization of thiosemicarbazides4a-cby mercuric oxide afforded 3-(5-(sub-amino)-1,3,4-oxadiazol-2-yl)-propanone6a-c. The reaction of4a-cwith phosphorus oxychloride gave 3-(5-(sub-amino)-1,3,4-thiadiazol-2-yl)-propanone7a-c. Treatment of4a-cwith ethyl-bromoacetate or alpha-bromopropionic acid gaveN '-(3-sub-thiazolidin-2-ylidene)-butanehydrazide8a-cand (N '-(3-sub-oxothiazolidin-2-ylidene)-butanehydrazide9a-c. Chlorination of oxothiazolidine-hydrazide9a-cby phosphorus oxychloride affordedN-(3-sub-4-oxothiazolidine)-butane-hydrazonoyl-chloride10a-c. The reaction of10a-cwith mercaptoacetyl-chloride yielded 2-((4-benzoyl-thiopyrane) hydrazono)-3-sub-thiazolidinone11a-c. Also, reacted of10a-cwith hydrazine hydrate affordedN ''-(3-sub-oxothiazolidine)-butane-hydrazon-hydrazide12a-c. The 3-sub-2-((pyridazine) hydrazono) thiazolidinone13a-cwas obtained by cyclization of12a-cvia refluxing in DMF. The reaction and cyclized of9a-cwith chloroacetyl-chloride in ethanolic KOH afforded 1-((3-sub-4-oxothiazolidine) amino)-azepine-dione14a-c. The chemical structures of the new compounds have been confirmed by diverse spectroscopy analyses such as IR, NMR, MS, and elemental analysis. The synthesized compounds were tested for their antimicrobial activity and these compounds were considered (Pyridazin-hydrazono-thiazolidinone13a-c, oxothiazolidin-azepinedione14a-c,N-thiazolidin-hydrazon-hydrazide12a-c, and thiopyran-hydrazono-thiazolidinone11a-c) the most effective as antimicrobial activity.

Automated summary

The paragraph describes the synthesis of various compounds by reacting 4-oxo-4-phenylbutanehydrazide with different aryl or alkyl isothiocyanates, followed by cyclization and desulfurization steps. The antimicrobial activity of the synthesized compounds was tested, and some of them showed promising activity, including Pyridazin-hydrazono-thiazolidinone, oxothiazolidin-azepinedione, N-thiazolidin-hydrazon-hydrazide, and thiopyran-hydrazono-thiazolidinone.