C-C Bond Cleavage of -Pyridinium Amides: A Synthetic Approach to Hydantoin Structures

This study reports a mild reaction-condition approach for the direct C-C bond cleavage of amides to form hydantoin structures in the presence of 4-methylpyridine and a base. This approach presents an amide C-C bond cleavage strategy enabling nucleophilic addition to the amide carbonyl involving a reactive spiro intermediate. A broad spectrum of pseudo peptide Ugi adducts as bifunctional starting materials was synthesized and used in this transformation. The mechanistic pathway of this reaction was investigated using experimental and theoretical studies.