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A New Multicomponent Reaction for the Synthesis of Amides

机译:一种用于合成酰胺的新型多组分反应

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摘要

In furtherance of our research on the green and environmentally benign synthesis of heterocyclic and pharmaceutical compounds, we now report a novel multicompo-nent route to amides via the condensation of arenes, 2-aminobenzimidazole, and cyclic anhydrides in the presence of crystalline nanoparticle nickel-ferrite silica-propyl supported glucosamine (NiFe2O4@SiO2-propyl@glucosamine, Figure 1) as an efficient, reusable and heterogeneous catalyst in water as green solvent. The NiFe2O4@SiO2-pro-pyl@glucosamine magnetic nanoparticles (MNPs) were synthesized in three steps from commercially available materials. MNPs were coated by silica using a sol-gel process which we have previously described. To check the efficiency of our new catalyst in organic reactions, the condensation of toluene (1.0 mmol), phthalic anhydride (1.0 mmol), and 2-aminobenzimidazole (1 mmol) was attempted with different catalysts in various solvents. None of the desired N-(l-hydro-benzodimidazole-2-yl)-2-(4-methylbenzoyl) benzoamide (6b) was obtained after stirring the reaction mixture for 24 h at room temperature in the absence of catalyst (Table 1, entry 1). The reactions were carried out in the presence of HCl, K-10, HY-zeolite, NiFe2O4, SiO2 and NiFe2O4@SiO2 and showed low yields of product 6b even after 5h (Table 2, entries 2-7). The yield of the product improved remarkably to 96 after stirring the components at room temperature for 1h in the presence of NiFe2O4@SiO2-propyl@glucosamine (Table I, entry 8). Entries 8-11 show that this mul-ticomponent reaction did not lead to the product 6b in weak polar solvents such as chloroform and dioxane, but the efficiency and the yield of the reaction in water were high.
机译:为了进一步研究杂环化合物和药物化合物的绿色和环境友好合成,我们现在报道了一种新的多组分途径,通过芳烃、2-氨基苯并咪唑和环酐在结晶纳米颗粒镍铁氧体二氧化硅丙基负载氨基葡萄糖(NiFe2O4@SiO2-propyl@glucosamine,图1)的存在下缩合酰胺,作为一种高效、可重复使用和非均相催化剂在水中作为绿色溶剂。NiFe2O4@SiO2-pro-pyl@glucosamine磁性纳米颗粒(MNPs)由市售材料分三步合成。MNP使用我们之前描述的溶胶-凝胶工艺用二氧化硅包被。为了验证我们的新催化剂在有机反应中的效率,尝试在各种溶剂中用不同的催化剂缩合甲苯(1.0 mmol)、邻苯二甲酸酐(1.0 mmol)和2-氨基苯并咪唑(1 mmol)。在没有催化剂的情况下,在室温下搅拌反应混合物24小时后,没有获得所需的N-(l-氢苯并[d]咪唑-2-基)-2-(4-甲基苯甲酰基)苯甲酰胺(6b)(表1,条目1)。反应在HCl、K-10、HY沸石、NiFe2O4、SiO2和NiFe2O4@SiO2存在下进行,即使在5h后,产物6b的收率也很低(表2,条目2-7)。在室温下,在NiFe2O4@SiO2-propyl@glucosamine存在下搅拌组分1小时后,产物的收率显着提高到96%(表I,条目8)。条目8-11表明,在氯仿和二恶烷等弱极性溶剂中,这种多组分反应没有导致产物6b,但在水中反应的效率和收率较高。

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