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

Abstract

A benign and straightforward method to access quinazolinones have been developed using easily preparable Cu3(BTC)2 MOF as a sustainable solid‐Lewis acid catalyst under mild condition. Cu3(BTC)2 MOF was prepared and characterized using various analytical tools such as PXRD, FT‐IR, SEM, TGA, and ICP‐OES. Synthesis of the quinazolinone is catalyzed by the presence of coordinatively unsaturated open CuII sites in Cu3(BTC)2 MOF using renewable ethanol as a solvent with minimum copper loading (0.07 mmol) without any harsh reaction condition. A series of substituted quinazolinones were synthesized with good to excellent yields. The efficiency of the present framework copper catalysts was rationalized by comparing with other MOFs and homogeneous catalytic systems. The stability of the catalyst was demonstrated by six consecutive runs and heterogeneity test, which was also evidenced from the technical supports such as PXRD, FT‐IR and SEM analyses of the recovered catalyst.

α,β-Enone Borylation by Bis(Pinacolato)Diboron Catalyzed by Cu3(BTC)2 Using Cesium Carbonate as a Base

“…Therefore, Cu 3 (BTC) 2 has been widely used as a catalyst to promote a variety of Lewis acidcatalyzed organic reactions including condensation [28], the ring opening of epoxide [29], and cyclizations [30][31][32], among others [33][34][35]. Furthermore, Cu 2+ ions in Cu 3 (BTC) 2 MOF with unsaturated positions have also been reported in many organic transformations like the oxidation of styrene [36], aerobic epoxidation of olefin [37], CO oxidation [38], oxidative synthesis of quinazolinones [39], synthesis of tetrazoles [40], arene borylation [41], Friedel-Crafts alkylation of indoles with nitroalkenes [42], dehydrogenative coupling of dimethylphenylsilane with phenol [43], acetalization of benzaldehyde [44], aldol synthesis of pyrimidine-chalcone hybrids [45], and hydrogenation of acetophenone by silanes [46].…”

A base-free Chan–Lam reaction catalyzed by an easily assembled Cu(II)-carboxylate metal-organic framework

“…However, the Chan-Lam cross-coupling reaction, the oxidative coupling of amines and arylboronic acids catalyzed by Cu salts, represents one of the most powerful and straightforward tools to construct C-N bonds. [8][9][10][11][12][13] This process is mild, convenient, and cheap, offering an alternative to complementary methods using noble metals. So far, various homogeneous Cu catalysts have been used for the Chan-Lam reaction to access N-arylamine subunits.…”

Selective Synthesis of 2-(1,2,3-Triazoyl) Quinazolinones through Copper-Catalyzed Multicomponent Reaction

“…An example was reported by Akhlaghinia et al [17], who described an efficient protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones using Cu(I) functionalized with aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide [SBA-16/GPTMS-TSC-Cu(I)] as a catalyst in the condensation of 2-aminobenzamide and an aldehyde under solvent-free conditions (Figure 2A). In 2020, Suresh et al [18] reported the copper-catalyzed oxidative synthesis of quinazolinones in the presence of the reusable catalyst based in Cu3(BTC)2 (BTC = 1,3,5-benzene tricarboxylate) under mild condition, as shown in Figure 2B. There remains, however, a need for in-depth research on the synthesis of highly functionalized quinazolinones from various substrate combinations.…”