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Unusual Reactivity of Isoquinolinones Generated by Silver Catalyzed Cycloisomerizations of Imines Derived from ortho-Alkynylsalicylaldehydes.

8-Isoquinolinones derived from a silver-catalyzed cycloisomerization of in situ formed ortho-alkynylsalicylaldimines react with one equivalent of acetylenedicarboxylate derivatives to give pyrano[2,3,4-ij]isoquinolines through a [4+2]-cycloaddition reaction. When two equivalents of the alkyne are used, structurally complex benzo[de]chromenes are obtained through an intricate cascade process comprising unusual formal [4+2]- and [2+2]-cycloadditions followed by several ring-opening and ring-closing processes.

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