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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(1 H )-ones via one-pot three-component reaction
Research on Chemical Intermediates ( IF 2.8 ) Pub Date : 2020-05-26 , DOI: 10.1007/s11164-020-04179-8
Niusha Nikooei , Mohammad G. Dekamin , Ehsan Valiey

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(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.



中文翻译:

苯-1,3,5-三羧酸官能化的MCM-41是一种新颖且可回收的杂化催化剂,可通过一锅三组分反应快速高效地合成2,3-二氢喹唑啉-4(1 H)-一

制备了新型的杂化有机硅苯1,3,5-三羧酸官能化MCM-41(MCM-41-Pr-BTA),并通过傅里叶变换红外光谱,场发射扫描电子显微镜,透射电子显微镜,Brunauer-Emmett-Teller,热重分析和能量色散X射线光谱法来评估官能团,结晶度,表面积,形态,粒径分布和官能团的负载。有趣的是,与更知名的三烷氧基丙基硅烷相比,本研究中使用的1,3-丙烯连接基将适当的催化活性纳入MCM-41骨架中。这种新的有机硅可以用作杂化纳米催化剂,以快速有效地合成2,3-二氢喹唑啉-4(1 H-一种衍生物,作为重要的药物支架,可通过水溶介质通过等角酸酐和芳族醛与伯胺或铵盐的三组分一锅缩合在水性介质中使用。该方法具有许多优点,例如催化剂用量低,产率高至优异,反应时间短,在绿色条件下操作和后处理简单。

更新日期:2020-07-06
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