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•N-Propargyl 2-(imidazole-2-yl)indoles were investigated in cyclization reactions.•Zn(OTf)2-catalyzed reaction gave cyclization product at C-3 of the indole nucleus.•Base-promoted reaction led to cyclization at N-1 of indole.•The use of 3-aryl propargylamines gave a cascade cyclization.
The cyclization reactions of 2-(N-propargyl)imidazole-2-yl)indoles (synthesized via the hydroamination reaction between N-propargyl indole-2-carboxamides and propargylamine) have been investigated under Lewis acid- and base-promoted conditions. The polyheterocyclic compounds thus obtained were shown to possess promising photophysical properties.