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

Abstract

AbstractThe oxidative addition of N‐aminophthalimide to substituted 2‐vinylfurans provides monophthaloylhydrazones of (2Z)‐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.