One‐Pot Three‐Step Synthesis of Naphtho[2,3‐a]carbazole‐ 5,13‐diones using a Tandem Radical Alkylation–Cyclization– Aromatization Reaction Sequence

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Abstract
A three‐step, one‐pot tandem reaction including radical nucleophilic alkylation/cyclization/aromatization was developed using 0.3 equivalents of silver(I) acetate (AgOAc) as the catalyst and 2 equivalents of ammonium persulfate [(NH4)2S2O8] as the oxidant. This strategy is highly efficient for the assembly of pentacyclic complex carbazoles from aryl‐fused bromobenzoquinones and indol‐3‐ylpropanoic acid acids in 52–72% overall yields (three steps). This new approach provides a significant improvement over the previously reported methods and would greatly facilitate analog library construction of pentacyclic complex carbazoles and benefit further biological evaluation of these compounds.

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