Sc(OTf)3-Catalyzed Formal [3 + 3] Cycloaddition Reaction of Diaziridines and Quinones for the Synthesis of Benzo[e][1,3,4]oxadiazines

A formal [3 + 3] cyclization reaction of diaziridines and quinones has been developed offering 1,3,4-oxadiazinanes in generally high yields (up to 96%). The reaction was catalyzed by Sc(OTf)3 with a large substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and the dipolar quinones was found to be essential to enable this reaction.