An efficient synthesis of 1,2,3,4-tetrahydrobenzo[]quinoline derivatives through PdCl-catalyzed, TBHP-promoted, and toluene-mediated dehydrogenation/[4+2] cycloaddition of saturated cyclic amines with 2-alkynylbenzaldehydes was developed. On the contrary, when the reaction medium was changed from toluene to DMSO/HO, another class of important compounds, naphthyl chain amines, formed via a dehydrogenation-intermolecular condensation-C-N bond cleavage-intramolecular condensation pathway, was obtained with good selectivity.
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