Expeditious synthesis of 3-arylidenelactams and 3-arylidenelactones from N-tosylaziridine derivatives

An expeditious synthetic method of 3-arylidenelactams was developed starting from N-tosylaziridines, which were made from the reaction of N-tosylimines and cinnamyl bromides by using the sulfur ylide chemistry. The regioselective ring-opening reaction of N-tosylaziridines with anilines, as external nucleophiles, and the following lactamization afforded 3-arylidenelactams. In the absence of external nucleophiles, intramolecular lactonization occurred to afford 3-arylidenelactones.