A regio- and chemoselective silver-catalyzed one-pot synthesis of benzo[b][1,7]- and benzo[c][2,7]-naphthyridines has been developed via a sequential Michael addition and silver-mediated cyclization strategy. The protocol exhibits excellent selectivity, high yields, and broad functional group tolerance. The resulting polyfunctionalized benzo[c][2,7]-naphthyridine scaffolds were further investigated as key intermediates toward the synthesis of Perlolidine analogues, highlighting their potential for the discovery of novel bioactive compounds and alkaloid framework.

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