Heterocyclic systems containing S/N regioselective nucleophilic competition: facile synthesis, antitubercular and antimicrobial activity of thiohydantoins and iminothiazolidinones containing the benzo[b]thiophene moiety

Abstract

The required compounds N-aryl-N'-(3-chloro-2-benzo[b]thenoyl)–thioureas 1a–k were prepared by condensing 3-chloro-2-benzo[b]thenoyl chloride with different arylamines using ammonium thiocyanate, which in turn when treated with chloroacetic acid, yielded 1-aryl-3-(3-chloro-2-benzo[b]thenoyl)thiohydantoins 2a–k, while in the presence of sodium acetate treated with chloroacetic acid, yielded 2-arylimino-3-(3-chloro-2-benzo[b]thenoyl)-4-thiazolidinones 3a–k. All the synthesized compounds were screened for their antitubercular and antimicrobial activities. Some selected compounds were selected for their further antitubercular screening

Keywords

• iminothiazolidinone
• thiohydantoin
• antitubercular activity
• antimicrobial activity