Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights

Abstract

Experimental results and computational insights explain the key role of transition-metal catalysis/Brønsted acid synergism in the achievement of the sequential regioselective direct heteroarylation/ cyclocondensation reactions of β-(2-aminophenyl)-α,β-ynones with a variety of electron-rich aromatic heterocyclic/arenes to afford quinoline-(hetero)aromatic hybrids. The first approach to the synthesis of 4-(1Hpyrrol-2-yl)quinolines is described. The effectiveness of various transition metals is compared.

Advances in gold catalyzed synthesis of quinoid heteroaryls

“…Synthesis of 4-(1H-pyrrol-2-yl)quinoline (2x) C-H functionalization site were temperature, reaction medium, and catalyst characteristics. 115…”

“…In 2w, the most important factors influencing the selectivity of the C–H functionalization site were temperature, reaction medium, and catalyst characteristics. 115 …”