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A series of N-methoxy- and N-para-methoxyphenylacetamides simultaneously substituted at the α position by a benzyl and an allyl group have been treated with phenyliodine(III)bis(trifluoroacetate) to generate stabilized N-acylnitrenium intermediates. It has been observed that, when starting from N-methoxy substituted amides, such intermediates are intramolecularly trapped by nucleophilic arene rings...
A new application of the hypervalent iodine reagent phenyliodine(III)bis(trifluoroacetate) (PIFA) has been developed for the construction of a series of N, O, S-containing heterocycle-fused quinolinone derivatives in a general and efficient way. An alternative approach to the formation of these novel tricyclic heterocycles by a PIFA mediated aryl-heteroaryl coupling reaction is also presented.
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