SYNTHESIS OF UTED-5,6-DIMETHYLPYRROLO-[2,3-D]-1,3-OXAZIN-4-ONES AS ANTIFUNGAL AGENTS

A series of novel 5,6-dimethylpyrrolo[2,3-a]-1,3-oxazin-4-ones were sy nthesized from -amino-3-tert-butoxycarbonyl-4,5-dimethylpyrroles. Two methods were used, cyclodehydration of 2-acylamino-3-carboxypyrroles w ith acetic anhydride and direct conversion of the 5,6-dimethylpyrrolo[ 2,3-d]-1,3-oxazin-2,4-diones to the title compounds with an anhydride directly providing the 2 substituent. Molecular modeling techniques re vealed that these pyrrolo[2,3-a]oxazinones were rigid analogues of the allylamine antifungals. The compounds were tested for in vitro activi ty against Tricophyton and Scopulariopsis sp.