In the search for novel approaches to the preparation of different heterocyclic derivatives, our group has recently focussed on the enormous potentiality that some hypervalent iodine reagents can provide in organic synthesis. Thus, the clean transformations achieved, the mild conditions employed, and the low toxicity associated to it, prompted us to include PIFA[phenyliodine(III)bis(trifluoroacetate)] in our synthetic plans. In this context, when treated with PIFA, N-methoxyamides are transformed into electrophilic N-acylnitrenium ions, which can be trapped intramolecularly by aromatic rings acting as the nucleophilic partner. Our efforts to apply this strategy to the synthesis of quinolinones and benzodiazepin-2-ones will be disclosed in this paper.
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