Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 as a novel and recoverable hybrid catalyst for expeditious and ef
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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 Niusha Nikooei1 · Mohammad G. Dekamin1 · Ehsan Valiey1 Received: 30 March 2020 / Accepted: 11 May 2020 © Springer Nature B.V. 2020
Abstract 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-dihydroquinazolin4(1H)-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. Keywords MCM-41 organosilica · Grafting · Mesoporous materials · Hybrid materials · Acid catalysis · Nanoreactor · Heterogeneous catalysis · Green chemistry · Quinazoline derivatives · Ring closure
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04179-8) contains supplementary material, which is available to authorized users. * Mohammad G. Dekamin [email protected] 1
Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846‑13114, Iran
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Introduction Heterogeneous catalysis has fascinated greater attention because of easy separation and recyclability. The unique properties of heterogeneous catalysts such as high thermal stability, structural diversity, easy modifications, strong absorption and low toxicity have made them attractive in some industrial applications such as chemical, pharmaceutical, automobile and petrochemical industries [1–6]. One of the best-known support materials having silica structure is mesoporous MCM-41, which has a hexagonal array of one-dimensional pore structures. This mesoporous silica can be obtained by a simple procedure and shows outstanding structural properties with the high specific surface area (up to 2000 m2 g−1) and pore diameter in the range 15–100 Å [7–11]. The acidity of MCM-41 is low. Hence, to overcome this limitation, different methods have been improved to increase their a
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