Novel Alternative for the N−N Bond Formation through a PIFA-Mediated Oxidative Cyclization and Its Application to the Synthesis of Indazol-3-ones

The synthesis of a series of N,N'-disubstituted indazolone derivatives starting from methyl anthranilates is presented. This general approach features a novel and easy way for access to the target N-heterocycles by formation of a new N-N single bond. The key cyclization step embraces the formation of an N-acylnitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its succeeding intramolecular trapping by the amine moiety under rather mild experimental conditions.