Novel alternative for the N-N bond formation through a PIFA-mediated oxidative cyclization and its application to the synthesis of indazol-3-ones |
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Authors: | Correa Arkaitz Tellitu Imanol Domínguez Esther Sanmartin Raul |
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Institution: | Departamento de Química Organica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain. |
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Abstract: | 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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