SYNTHESIS AND ANTIMICROBIAL EVALUATION OF OXAZOLE-2(3H)-THIONE AND 2-ALKYLSULFANYL-1,3-OXAZOLE DERIVATIVES

摘要

The preparation of oxazole-2(3H)-thiones (OXTs) by condensation of thiocyanic acid on a-hydroxycarbonyl substrates has been revisited. Extension to more complex scaffolds afforded chiral OXTs, whereas carbohydrate-fused 2-alkylsulfanyl-1,3-oxazolines led to original hemiaminal structures. A survey of the reactivity of OXTs with various electrophiles showed S- or N-chemoselectivity based on HSAB parameters. Antimicrobial evaluation of selected synthesized compounds was carried out, from which the hemiaminal 15 emerged as a promising antifungal agent.