Reaction of some antiinflammatory 17 beta-(2-aminooxazol-4-yl) steroids with hydrogen peroxide. Synthesis of steroid-17-spiro-5'-oxazolidine-2',4'-diones.
The heterocyclic moiety of 17 beta-(2-aminooxazol-4-yl) steroids is sensitive to the oxidizing action of hydrogen peroxide and yields products mainly from the opening of the amino-oxazole ring. Unlike simple 2-aminooxazoles, it does not rearrange to 2-imidazolone and the expected steroidal hydroperoxyimidazolidinones were not detected. Among the substances we isolated, N-(aminocarbonyl)-17 alpha-hydroxy-17-carboxamides (2a) and (3a) undergo spontaneous cyclization, in the reaction conditions, giving steroid-17-spirooxazolidinediones (2d) and (3d). Spirane (2d) was synthesized in high yields from (2a) in strongly alkaline medium.
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D006861:Hydrogen Peroxide; D010080:Oxazoles / Q000138:chemical synthesis; D013141:Spiro Compounds / Q000138:chemical synthesis; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis
D000893:Anti-Inflammatory Agents; D010080:Oxazoles; D013141:Spiro Compounds; D013260:Steroids, Heterocyclic; D006861:Hydrogen Peroxide