Copper Catalyst-Supported Modified Magnetic Chitosan for the Synthesis of Novel 2-Arylthio-2,3-dihydroquinazolin-4(1<i>H</i>)-one Derivatives via Chan–Lam Coupling

Abstract

In this paper, magnetic chitosan is used as a support for the immobilization of copper catalyst (Cu@MChit). The fabricated catalyst is successfully synthesized and characterized by several techniques. The activity of Cu@MChit catalyst is evaluated in the synthesis of novel derivatives of 3-alkyl-2-arylthio-2,3-dihydroquinazolin-4(1H)-ones. The products are synthesized in three simple steps via Chan–Lam coupling reaction. The synthetic route is based on the reaction of isatoic anhydride and an amine, followed by the reaction with carbon disulfide. Cu@MChit-catalyzed reaction of the obtained intermediate with phenylboronic acid leads to the desired products. The scope of the reaction is confirmed by using various amine and phenylboronic acid derivatives and the products are obtained in high isolated yields.

Keywords

• magnetic chitosan
• 2-arylthio-2,3-dihydroquinazolin-4(1<i>H</i>)-one
• Chan–Lam coupling
• quinazolinone
• copper catalyst
• chitosan