Synthesis of 6-Nitroderivatives of Oxazolo[3,2-a]-pyridines and Their Reactions with Nucleophiles

Abstract

5-Nitro-2-pyridone can be selectively N-phenacylated, and the resulting phenacylpyridones I undergo cyclization to 6-nitrooxazolo[3,2-a]pyridinium salts II. These salts II readily react with ammonia and aliphatic amines leading to the products of pyridine ring opening - previously unknown 1-amino-2-nitro-4-(oxazole-2-yl)butadienes-1,3. Reaction of salts II with water lead to hydrolytic cleavage of the oxazole fragment.

Keywords

• 5-Nitro-2-pyridone
• oxazolo[3
• 2-a]pyridine
• butadiene
• nitrodiene
• aminodiene
• oxazolyldiene