Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 as a novel and recoverable hybrid catalyst for expeditious and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones via one-pot three-component reaction

• Published in: Research on chemical intermediates 2020-08, Vol.46 (8), p.3891-3909
• Main Authors: Nikooei, Niusha, Dekamin, Mohammad G., Valiey, Ehsan
• Format: Article
• Language: English
• Subjects: Aldehydes; Amines; Aqueous solutions; Catalysis; Catalysts; Catalytic activity; Chemical synthesis; Chemistry; Chemistry and Materials Science; Electron microscopy; Field emission microscopy; Field emission spectroscopy; Fourier transforms; Functional groups; Gravimetric analysis; Hydrocarbons; Inorganic Chemistry; Microscopy; Morphology; Particle size distribution; Physical Chemistry; Propylene; Silanes; Spectrum analysis; Stress concentration; Trimesic acid
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-020-04179-8

Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 (MCM-41-Pr-BTA), as a novel hybrid organosilica, was prepared and properly characterized by the Fourier-transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, Brunauer–Emmett–Teller, thermal gravimetric analysis and energy-dispersive X-ray spectroscopy to evaluate the functional groups, crystallinity, surface area, morphology, particle size distribution and loading of functional groups. Interestingly, the 1,3-propylene linker used in this study incorporates appropriate catalytic activity into the MCM-41 framework compared to the more known trialkoxypropyl silanes. This new organosilica can be used as a hybrid nanocatalyst for the expeditious and efficient synthesis of 2,3-dihydroquinazolin-4(1 H )-one derivatives, as an important pharmaceutical scaffold, in aqueous media via a three-component one-pot condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium salts. This method has several advantages such as low catalyst loading, high to excellent yields, short reaction times, working under green conditions and simple workup.