Abstract
New series of 1,3,4-thiadiazoles have been prepared via reaction of 1,3,4-thiadiazolenaminones 1 with N-phenyl 2-oxopropanehydrazonoyl chloride (2) in dioxane in the presence of triethylamine. Also, some new heterocycles incorporating 1,3,4-thiadiazole ring were obtained by reaction of 1,3,4-thiadiazolenaminones 1 with nitrogen-nucleophiles like hydrazine hydrate, 3-amino-1,2,4-triazole and 2-aminobenzimidazole. The structure of the new products was established based on elemental and spectral analysis. The relation between the structure of the products and their activity towards some microorganisms was studied and promising results were obtained.
Highlights
The chemistry of enaminones has received considerable attention due to their utility as building blocks in heterocyclic synthesis [1,2,3,4,5]
In continuation of our interest in synthesis of bioactive compounds [12,13,14,15,16], we have prepared a new series of 1,3,4-thiadiazoles via reaction of N-[3-aryl-5-(3-dimethylaminoacryloyl)-3H-[1,3,4]-thiadiazol-2-ylidene]-benzamides with 1,3-dipoles and some nitrogen
Molecules 2012, 17 nucleophiles to investigate the antimicrobial activity of the products and study their structure activity relationship (SAR) towards some microorganisms
Summary
The chemistry of enaminones has received considerable attention due to their utility as building blocks in heterocyclic synthesis [1,2,3,4,5]. We published the antimicrobial activity results of a series of N-[3-aryl-5-(3-dimethylaminoacryloyl)-3H-[1,3,4]-thiadiazol-2-ylidene]-benzamides, which showed promising activity [11]. Based on these findings, and in continuation of our interest in synthesis of bioactive compounds [12,13,14,15,16], we have prepared a new series of 1,3,4-thiadiazoles via reaction of N-[3-aryl-5-(3-dimethylaminoacryloyl)-3H-[1,3,4]-thiadiazol-2-ylidene]-benzamides with 1,3-dipoles and some nitrogen. Molecules 2012, 17 nucleophiles to investigate the antimicrobial activity of the products and study their structure activity relationship (SAR) towards some microorganisms
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