Knoevenagel Condensation Catalyzed by Sodium Silicate Under Solvent-Free Conditions

Abstract

Sodium silicate pentahydrate has been utilized as an efficient catalyst for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds to afford substituted olefins in yields of 80.6%～98.9% under solvent-free conditions at room temperature within a short time. The advantages of this procedure are mild reaction conditions, excellent yields, cleaner reaction profiles, and operational simplicity.

GRAPHICAL ABSTRACT      

微波辐射和加热条件下的无催化剂无溶剂Knoevenagel缩合反应

芳香醛和丙二腈在无催化剂无溶剂存在下在微波辐射或加热条件下可以发生Knoevenagel缩合反应,反应产率良好.     

L-Proline Catalyzed Solvent-Free Knoevenagel Condensation for the Synthesis of 3-Substituted Coumarins

L-Proline was utilized as an efficient organo-catalyst for the environmentally benign synthesis of 3-substituted coumarins by the Knoevenagel condensation of substituted 2-hydroxybenzaldehydes with reactive methylene compounds under solvent free conditions.     

Simple,Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate Under Solvent-Free Conditions

A simple, efficient, and green procedure for Knoevenagel condensation of aromatic aldehydes with malononitrile and ethyl cyanoacetate catalyzed by ethylenediammonium diacetate under solvent-free conditions at room temperature is reported. This method gives remarkable advantages such as a simple procedure, mild conditions, fast (1–45 min) reactions, and excellent yields. Additionally, the catalyst can be reused for at least five runs without significant decrease of the yields.      

酸性沸石分子筛催化Knoevenagel缩合反应

 在高硅／铝比的酸性沸石分子筛HY上实现了Knoevenagel缩合反应．Bronsted酸和Lewis酸均可催化Knoevenagel缩合反应．考察了羰基化合物和活泼亚甲基化合物的反应活性顺序．结果表明，羰基化合物的羰基极化程度越高，反应越容易进行；不同于碱催化时的Knoevenagel缩合反应，活泼亚甲基化合物的活泼氢的酸性并不是影响其反应活性的重要因素．     

Solvent-free Knoevenagel Condensations over TiO2

A study involving the scope of substrates in the Knoevenagel reaction under SFC has been conducted. Reactivity trends favored formation of the condensation product using both electron deficient and rich aryl aldehydes. A recycling study confirmed that the reaction medium could be used multiple times affording, with each run, the desired condensation product in excess of 95% conversion.     

Leucoemeraldine-Base-Catalyzed Knoevenagel Condensation

A facile method for Knoevenagel condensation has been developed by using Leucoemeraldine base as catalyst to give substituted alkenes in excellent yields. The recycling of the solid catalyst was investigated.     

无溶剂研磨条件下芳基亚甲基麦氏酸的合成

将芳香醛、麦氏酸与NaHCO₃置于研钵中, 在无溶剂存在下通过研磨可以发生缩合反应, 反应产率良好.     

碱性氧化铝催化芳醛与丙二腈的Knoevenagel缩合反应

无溶剂下,以碱性氧化铝为催化剂催化芳醛和丙二腈的Knoevenagel缩合反应,合成了一系列的芳基亚甲基丙二腈化合物。实验结果表明,该法具有操作和后处理简单、产率高、催化剂能够循环使用、对环境友好等优点,符合绿色化学的要求。     

环境友好催化剂壳聚糖催化Knoevenagel反应

用壳聚糖作为固相催化剂催化Knoevenagel反应,产率高,产品纯度好.壳聚糖无毒无害且能被微生物降解,对环境友好,是绿色催化剂.     

Melamine as a Green and Reusable Catalyst for Knoevenagel Condensation at Room Temperature Under Solvent-Free Conditions

A rapid, efficient, and ecofriendly protocol has been developed for the Knoevenagel condensation of active methylene compounds such as malononitrile or ethyl cyanoacetate with aldehydes in the presence of melamine with good to excellent yields at room temperature without solvent.     

Knoevenagel缩合反应研究的新进展

综述了近年来Knoevenagel缩合反应研究的新进展, 包括微波、超声波、固相合成、离子液体等新技术新试剂在该反应中的应用.     

脯氨酸离子液体催化Knoevenagel缩合反应

改进了1-丁基-3-甲基咪唑L-脯氨酸([bmim][Pro])功能化离子液体的合成路线,并将该离子液体用于催化含活泼亚甲基化合物与醛或酮的Knoevenagel缩合反应.在水介质中,室温下,该离子液体可快速催化上述Knoevenagel缩合反应,并选择性生成α,β-不饱和羰基化合物且分离收率可达到88％～97％.该脯氨酸离子液体循环重复使用6次后,催化活性没有明显的下降.此外,初步探讨了其催化过程机理.     

Knoevenagel Condensation Catalysed by Alumina

在Ａｌ２Ｏ３催化下活泼亚甲基化合物和羰基化合物进行克脑文格尔缩合反应，在温和的反应条件下得到较高收率的产物。将超声波辐射应用于该缩合反应使反应速度明显提高。     

Aqueous Knoevenagel Condensation Catalyzed by Aminopropyl-functionalized MCM-41

Since much more attention has been paid to the sustainable development, many researchers try to improve conventional chemical process and find new and more, environmentally friendly routes1. Aqueous-phase reactions are of interest as environ- mentally ben…     

Knoevenagel Condensation between Benzaldehyde and Malononitrile Over Magnesium Phosphates

The Knoevenagel condensation between benzaldehyde and malonitrile over different magnesium phosphates was studied. The structure and chemical surface properties of each solid, which determine their catalytic activity, were found to depend on the synthetic procedure used. The results obtained were compared with their basicity measured by phenol adsorption and their dehydrogenation selectivity in the conversion of 2-hexanol.     

Green Approach for Knoevenagel Condensation of Aromatic Aldehydes with Active Methylene Group

An ecofriendly and economical method of Knoevenagel condensation of aromatic aldehydes with malononitrile catalyzed by lemon juice, a natural catalyst, in the absence of any solvent is described.     

离子液体中微波促进的Knoevenagel缩合反应

以离子液体1-丁基3-甲基咪唑四氟硼酸盐为反应溶剂，氨基乙酸为催化剂，在微波辐射下，醛和活泼亚甲基类化合物发生的Knoevenagel缩合反应速度能被极大地提高，8种缩合产物被快速高收率地合成。     

A Simple,Efficient and Green Procedure for the Knoevenagel Condensation of Aldehydes with N-Methylpiperazine at Room Temperature under Solvent-Free Conditions

Knoevenagel condensation of aromatic, aliphatic, and heteroaromatic aldehydes with active methylene compounds such as ethylcyanoacetate, malononitrile, and cyanoacetamide proceed very smoothly at room temperature by simply mixing the ingredients together under solvent-free conditions in the presence of N-methylpiperazine in excellent yields of the E-configured products.     

离子液体功能化二氧化硅催化Knoevenagel反应

在100 ℃, 无外加溶剂条件下, 离子液体功能化二氧化硅催化一系列芳醛和活泼亚甲基化合物进行Knoevenagel 缩合反应, 以高产率生成相应产物. 当反应底物为水杨醛与氰基乙酸乙酯的时候, 产物为3-乙氧基羰基香豆素, 这是水杨醛和氰基乙酸乙酯缩合关环, 再发生氰基醇解的产物. 采用离子液体功能化二氧化硅作为反应催化剂, 反应后催化剂可回收再利用.