A series of carbamate-containing derivatives of 1,2-and 1,4-oxazine, isoxazoline, isoxazole, benzimidazole-3-oxide, and indole were obtained by [3 + 2]-cycloaddition and ring-closure reactions. The antifungal activity of the synthesized compounds was studied in vitro against Microsporum canis, Trichophyton rubrum, and Candida albicans. Among the tested compounds, the maximum antifungal activity was observed for tautomeric 5(6)-alkoxycarboxamido derivatives of 2-aryl-1-hydroxybenzimidazole-3-oxide sodium salts and 1,2-oxazines.