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Highly Effective Synthesis of 1-thioamidoalkyl-2-naphthols and Tetrahydropyridines Using a Nanostructured Silica-based Catalyst Under Mild Conditions
Combinatorial Chemistry & High Throughput Screening ( IF 1.6 ) Pub Date : 2021-08-31 , DOI: 10.2174/1386207323666200914092345
Navid Irannejad-Gheshlaghchaei 1 , Seyed Sajad Sajadikhah 1
Affiliation  

Aim and Objective: Nano-2-[N',N'-dimethyl-N'-(silica-n-propyl)ethanaminium chloride]- N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4]) was used as a highly effective and heterogeneous silica-based nanostructured catalyst for the synthesis of 1-thioamidoalkyl-2-- naphthols and substituted tetrahydropyridines.

Material and Methods: The expected products were prepared in mild conditions. In this work, three novel 1-thioamidoalkyl-2-naphthols and two new tetrahydropyridine derivatives were synthesized and characterized by IR, 1H and 13C NMR and Mass spectroscopy.

Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano-[DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes and ethylacetoacetate under solvent-free and mild conditions.

Conclusion: The reaction results were found to be better compared to the literature in terms of one or more of these factors: yield, time, and the reaction media. All the products were purified by recrystallization from EtOH, and without column chromatography, being in good agreement with the green chemistry protocols.



中文翻译:

在温和条件下使用纳米结构二氧化硅基催化剂高效合成 1-硫代氨基烷基-2-萘酚和四氢吡啶

目的和目的:Nano-2-[N',N'-dimethyl-N'-(silica-n-丙基)ethanaminium chloride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4])用作一种高效的非均相二氧化硅基纳米结构催化剂,用于合成 1-硫代氨基烷基-2-萘酚和取代的四氢吡啶。

材料与方法:预期产品在温和条件下制备。在这项工作中,合成了三种新型 1-硫代酰胺烷基-2-萘酚和两种新型四氢吡啶衍生物,并通过 IR、1 H 和13 C NMR 和质谱进行了表征。

结果:纳米-[DSPECDA][HSO 4 ] 催化2-萘酚与芳醛和硫代乙酰胺在绿色、温和、无溶剂条件下的一锅多组分缩合反应得到高收率的1-硫代氨基烷基-2-萘酚。该纳米催化剂还用于在无溶剂和温和条件下通过苯胺、芳基醛和乙酰乙酸乙酯的一锅多组分反应制备官能化四氢吡啶。

结论:发现反应结果在以下一项或多项因素方面优于文献:产率、时间和反应介质。所有产物均经乙醇重结晶纯化,无需柱层析,符合绿色化学方案。

更新日期:2021-06-29
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