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Paper | Special issue | Vol 88, No. 2, 2014, pp.1013-1028
Published online, 11th October, 2013
DOI: 10.3987/COM-13-S(S)56
Synthesis and Antimicrobial Evaluation of Oxazole-2(3H)-thione and 2-Alkylsulfanyl-1,3-oxazole Derivatives

Sandrina Silva,* Filipa V. M. Silva, Jorge Justino, Amélia Pilar Rauter, Patrick Rollin, and Arnaud Tatibouët

*Department of Chemistry, University of Orléans, rue de Chartres- BP 6759, F-45067 Orléans Cedex 2, France

Abstract

The preparation of oxazole-2(3H)-thiones (OXTs) by condensation of thiocyanic acid on α-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.