KCC-1-NH2-DPA: an efficient heterogeneous recyclable nanocomposite for the catalytic synthesis of tetrahydrodipyrazolopyridines as a well-known organic scaffold in various bioactive derivatives

IF 4.2 3区材料科学 Q2 MATERIALS SCIENCE, COMPOSITES

Nanocomposites Pub Date : 2019-10-02 DOI:10.1080/20550324.2019.1681623

Sajjad Azizi, N. Shadjou, M. Hasanzadeh

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引用次数: 17

Abstract

Abstract In this study, a novel approach has been used for the efficient synthesis of tetrahydrodipyrazolopyridine derivatives (5a–m) via a four-component one-pot condensation reaction of aromatic aldehydes, hydrazinehydrate, ethyl acetoacetate, and ammonium acetate in the presence of KCC-1-npr-NH2-DPA as an advanced nano-catalyst in ethanol under reflux conditions at 30 min. For this purpose, mesoporous fibrous nano-silica functionalized by dipenicillamine as a novel nanocatalyst (KCC-1-npr-NH2-DPA) was synthesized using a hydrothermal protocol. KCC-1-npr-NH2-DPA nano-catalyst is easily recyclable eight times without the considerable loss of catalytic activity. Other remarkable features include the short reaction time, simple work-up procedure and providing excellent yields (89–98%) of the products under mild reaction conditions. Furthermore, the effects of solvent, concentration of catalyst, time and temperature for the synthesis of tetrahydrodipyrazolopyridine (5a) were studied. Graphical Abstract

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KCC-1-NH2-DPA:一种高效的非均相可回收纳米复合材料，用于催化合成四氢二吡唑吡啶，是各种生物活性衍生物中众所周知的有机支架

摘要本研究以KCC-1-npr-NH2-DPA为高级纳米催化剂，在回流条件下30 min，通过芳香醛、水合肼、乙酰乙酸乙酯和乙酸铵的四组分一锅缩合反应，高效合成了四氢二吡唑吡啶衍生物(5a-m)。为此，采用水热法合成了二青霉胺功能化的介孔纤维纳米二氧化硅作为新型纳米催化剂(KCC-1-npr-NH2-DPA)。KCC-1-npr-NH2-DPA纳米催化剂易于回收八次，且催化活性损失不大。其他显著的特点包括反应时间短，处理程序简单，在温和的反应条件下提供优异的产品收率(89-98%)。进一步研究了溶剂、催化剂浓度、时间和温度对四氢二吡唑吡啶(5a)合成的影响。图形抽象

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