Synthesis of novel 3-(quinazol-2-yl)-quinolines via SNAr and aluminum chloride-induced (hetero) arylation reactions and biological evaluation as proteasome inhibitors
Abstract
A new series of 3-(quinazol-2-yl)-quinolines was synthesized by SNAr reaction from easily prepared 4-chloro-2-(2-chloroquinolin-3-yl)quinazolines and a range of phenols and thiophenol as nucleophiles. The AlCl3-mediated CC bond formation was also successfully exploited to introduce aryl and hereroaryl substituents on one or both heterocyclic units. These procedures afford efficient syntheses of polysubstituted 3-(quinazol-2-yl)-quinolines in few steps and high yields. Some of these polysubstituted 3-(quinazol-2-yl)-quinolines inhibit the human 20S proteasome.
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Boualia et al-2020-Synthesis of novel 3-(quinazol-2-yl)-quinolines via SNAr and aluminum.pdf (332.81 Ko)
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