Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 9, Pages 3501-3505Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060070+
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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.
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