Novel oxazolidin-2-one-linked 1,2,3-triazole derivatives (<b>4a-k</b>) were synthesized by straightforward and versatile azide-enolate (3 + 2) cycloaddition. The series of compounds was screened for antifungal activity against four filamentous fungi as well as six yeast species of <i>Candida</i> spp. According to their efficiency and breadth of scope, they can be ordered as <b>4k</b> > <b>4d</b> > <b>4h</b> > <b>4a</b>, especially in relation to the activity displayed against <i>Candida glabrata</i> ATCC-34138, <i>Trichosporon cutaneum</i> ATCC-28592 and <i>Mucor hiemalis</i> ATCC-8690, <i>i.e.</i> compounds <b>4d</b>, <b>4h</b> and <b>4k</b> showed excellent activity against <i>C. glabrata</i> (MIC 0.12, 0.25 and 0.12 μg mL<sup>-1</sup>, respectively), better than that of itraconazole (MIC 1 μg ml<sup>-1</sup>). The activity of compound <b>4d</b> (MIC = 2 μg mL<sup>-1</sup>) was higher than that observed for the standard antifungal drug (MIC = 8 μg mL<sup>-1</sup>) against <i>Trichosporon cutaneum</i>, while compound <b>4k</b> displayed an excellent antimycotic activity against <i>Mucor hiemalis</i> (MIC = 2 μg mL<sup>-1</sup><i>vs.</i> 4 μg mL<sup>-1</sup> for itraconazole). In addition, we describe herein a novel mild and eco-friendly synthetic protocol for obtaining β-ketosulfones (adducts to afford compounds <b>4a-k</b>) from α-brominated carbonyls in an aqueous nanomicellar medium at room temperature.