SYNTHESIS OF 2,7-DISUBSTITUTED-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 synthesized from 2-amino-3-tert-butoxycarbonyl-4,5-dimethylpyrroles. Two methods were used, cyclodehydration of 2-acylamino-3-carboxypyrroles with 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 revealed that these pyrrolo[2,3-a]oxazinones were rigid analogues of the allylamine antifungals. The compounds were tested for in vitro activity against Tricophyton and Scopulariopsis sp.