The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru‐clusters/Ceria Catalyst

Abstract

Quinazolinones, an important class of heterocyclic compounds, have been widely used in pharmaceuticals because of their biological activity. However, the efficient and economical synthesis of quinazolinones has remained a challenge. A novel synthetic approach has now been developed to produce quinazolinones from olefins, CO, and amines over heterogeneous Ru-clusters/ceria catalyst in the absence of acids, bases, and oxidants. Furthermore, H O is generated as the only by-product. A series of quinazolinones with aromatic or non-aromatic substituents can be obtained in yields of up to 99 %. The Ru-clusters/ceria can be reused at least four times. The analysis of the E-factor (environmental impact factor) for the synthesis of 2-ethyl quinazolinone suggests that this system is more environmentally friendly than other processes reported previously.

Metal‐ and Catalyst‐Free Electrochemical Synthesis of Quinazolinones from Alkenes and 2‐Aminobenzamides

“…The oxidative cyclization of isatins with amidines can manufacture quinazolin‐4(3 H )‐ones (Scheme , e) . Recently, Wu's group and Wang's group have discovered that the reaction of alkenes with 2‐aminobenzamides can furnish quinazolinones in the presence of palladium and Ru‐clusters/Ceria, respectively (Scheme , f). Despite their contributions to the synthesis of quinazolinones, most of these synthesis methods rely on the stoichiometric amounts of oxidants, expensive noble metals, ligands/additives, elevated temperature, etc.…”

Surface properties of Ca, Ti‐doped CeO2 and their influence on the reverse water‐gas shift reaction

“…CeO 2 is used in a variety of catalytic processes, 1‐5 including the reverse water‐gas shift (RWGS) reaction 6‐8 . CeO 2 has a dual role in these processes, both as a mechanical support for a metallic species, such as Ni, Cu, or Co, 6,7,9 as well as an oxygen exchange material 10 .…”

Framework Copper Catalyzed Oxidative Synthesis of Quinazolinones: A Benign Approach Using Cu3(BTC)2 MOF as an Efficient and Reusable Catalyst

“…[6][7][8] Over the past decades, quinazolinones have been synthesized using various homogeneous transition metal-based catalysts such as vanadium, [9] irridium, [10] ironand cobalt catalysed redox condensation of ortho-substituted nitrobenzenes with amines, [11] palladium-catalyzed cyclocarbonylation with aryl halides [12] CÀ H amidation with benzyl alcohols [13] and copper-catalyzed condensation of 2-aminobenzamides with methylhetarene and2halobenzamide with arylnitrile. [14] Similarly, some of the heterogeneous catalytic systems such as carbon nanodots-iron oxide, [15] MCM-41 immobilized palladium, [16] ceria supported ruthenium, [17] vanillin-Schiff base-MCM-41 immobilized nickel [18] and by electrochemical process [19] were also reported for the synthesis of quinazolinones. Though several methodologies have been developed to achieve quinazolinone and its derivatives, most of them are suffering from its own limitations such as multistep procedure, corrosive or non-benign catalyst, stoichiometric amount of catalyst, arduous work-up, poor atom economy and relatively harsher reaction conditions.…”