A Role for Isatin Azomethine Imines as a Dipolarophile in Cycloaddition Reactions.

An unusual [2 + 3] cycloaddition of isatin azomethine imines (AIs) and in situ generated azaoxyallyl cations has been developed. It is the first example where AIs serve as the [C,O] 2-atom synthon in organic synthesis. This work not only reveals a new role of isatin AIs in cycloaddition reaction but also provides an efficient access to unprecedented spiroheterocycle compounds.