A critically important strategy for synthetic chemistry is the development of “domino” processes: those capable of concatenating multiple transformations into a single step. Such transformationsnot only provide an increase in synthetic efficiency, but also imply the development of a significantdegree of mechanistic understanding. We report herein a new domino reaction, in which achromium−manganese redox couple is employed both to catalytically reduce an o-hydroxy nitroareneand to oxidatively cyclize a subsequently formed imine. We find that the reaction is most effectivefor starting o-hydroxy nitroarenes with a strongly electron-withdrawing group at the para position.