Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

The oxidative addition of N ‐aminophthalimide to substituted 2‐vinylfurans provides monophthaloylhydrazones of (2 Z )‐hexa‐2,5‐diene‐1,4‐dione derivatives instead of 2‐furylaziridines by proceeding through an aziridination of the endocyclic furan C=C bond followed by a regio‐ and stereoselective rearrangement of the bicyclic intermediate. The formation of stable aziridines can then occur through the aziridination of the ( E )‐C=C bond of these phthaloylhydrazones. Detailed structure elucidations and mechanistic considerations are provided.