Ohmic Heating-Assisted Synthesis of 3‑Arylquinolin-4(1<i>H</i>)‑ones by a Reusable and Ligand-Free Suzuki–Miyaura Reaction in Water

Abstract

Potential bioactive 3-arylquinolin-4­(1<i>H</i>)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki–Miyaura coupling of 1-substituted-3-iodoquinolin-4­(1<i>H</i>)-ones with several boronic acids in water using Pd­(OAc)₂ as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4­(1<i>H</i>)-ones. After a simple workup, the Pd/catalyst-H₂O-TBAB system could be reused for at least seven cycles without significant loss of activity