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

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Summary

Introduction

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

Results and Discussion
Antimicrobial Activity
Antimicrobial Activity Screening and Structure Activity Relationship
General
Reaction of Enaminones 1a–d with Hydrazonoyl Chloride 2
Reaction of Enaminones 1a–d with Heterocyclic Amines
Reaction of Enaminones 1a–d with Hydrazine Hydrate
Agar Diffusion Well Method to Determine the Antimicrobial Activity
Conclusions

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