Facile synthesis of some new azetidinones and acetyl oxadiazoles bearing benzo[b]thiophene nucleus as a potent biological active agent

摘要

2-Hydrazinocarbonyl-3-chloro-5-phenoxybenzo[b]thiophene 1 has been prepared by the condensation of 3-chloro-5-phenoxybenzo[b]thiophenoyl chloride with hydrazine hydrate.Compound 1 on condensation with aromatic aldehyde furnishes 2-substituted benzalhydrazinocarbonyl-3-chloro-5-phenoxybenzo[b]thiophenes 2a-l,which on further cyclo-condensation with chloroacetyl chloride in the presence of triethyl amine afford 4-aryl-3-chloro-l-(3'-chloro-5'-phenoxy-2'-benzo[b]thiophenoylamino)-2-azetidinones 3a-l.Compounds 2a-l on reaction with acetic anhydride yield 2-(3'-chloro-5'-phenoxybenzo[b]thiophene-2'-yl)-4-acetyl-5-aryl-4,5-dihydro-l,3,4-oxadiazoles 4a-l.The structures of the compounds 2a-l,3a-l and 4a-l have been confirmed by elemental analysis and IR,~1H NMR and mass spectral data.All the compounds have been screened for their antitubercular activity towards Mycobacterium tuberculosis H_(37)Rv and antimicrobial activity against different microbes.