Catalyst-free nucleophilic substitution of hydrogen in quinoline rings by acylethynylpyrroles: stereoselective synthesis of 2-(E-2-acylethenylpyrrolyl)quinolines

Abstract

A new type of SNHAr reaction in the quinoline core under the action of available acylethynylpyrroles proceeds without halogenated reagents and any catalysts to stereoselectively afford 2-(E-2-acylethenylpyrrolyl)quinolines with a yield up to 78%.

Catalyst- and solvent-free regiospecific SNHAr phosphinylation of pyridines with H-phosphinates mediated by benzoylphenylacetylene

“…One of the promising routes to address this challenge is the nucleophilic substitution of hydrogen in a heteroaromatic ring, which is actively developing now. 29–33 An advantageous feature of this reaction is that it does not require preliminary functionalization, including halogenation, of the heterocyclic substrate that leads to environmentally dangerous waste.…”