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One-pot Pseudo-Domino Three-Component Knoevenagel Condensation Reaction in Water Enabled by Micellar Catalyst: Mechanism and Reactivity
Letters in Organic Chemistry ( IF 0.8 ) Pub Date : 2020-10-31 , DOI: 10.2174/1570178616666190701102542
Dini Ahanthem 1 , Devi Prasan Ojha 2 , Francis A.S. Chipem 1 , Warjeet S. Laitonjam 1
Affiliation  

The micellar catalysis is well-known for its hydrophobic effect that is the tendency of nonpolar groups to cluster within the lipophilic core so as to shield them from contact with an aqueous environment formed upon the dissolution of a surfactant in water. This provides a unique opportunity to establish organic transformations in greener solvents, such as water leading to organic waste control and easy product isolation protocols. Considering the significant interaction of thiobarbituric acid moieties in a biological macromolecule core, herein, a highly efficient procedure for the synthesis of biological and medicinal important 5-(arylmethylene)dihydro-2-thioxo-4,6(1H,5H)-pyrimidinediones via Knoevenagel condensation of thiobarbituric acids and aldehydes catalyzed by a surfactant, sodium dodecyl sulfate, is developed. The synthetic procedure shows the excellent activity of the micellar catalysts towards the aldehyde activation leading to a facile condensation. The application of the method is demonstrated by further synthesis of 5,5'-(4-arylmethylene)bis[dihydro-2-thioxo-4,6(1H,5H)- pyrimidinediones]. Theoretical studies of the reaction were also carried out to investigate the effect of electron releasing and electron-withdrawing group in benzaldehyde on the reaction.



中文翻译:

胶束催化剂在水中的一锅式伪多米诺三组分Knoevenagel缩合反应:机理和反应性

胶束催化以其疏水作用而众所周知,该疏水作用是非极性基团趋向于在亲脂性核内聚集的趋势,从而使它们不与表面活性剂溶解于水中形成的水​​性环境接触。这为在绿色溶剂(例如水)中建立有机转化提供了独特的机会,从而可以控制有机废物并简化产品分离流程。考虑到在生物大分子核心中硫代巴比妥酸部分的显着相互作用,本文提出了一种高效的方法,可通过以下步骤合成生物和医学重要的5-(芳基亚甲基)二氢-2-硫代氧杂4,6(1H,5H)-嘧啶二酮开发了表面活性剂十二烷基硫酸钠催化的硫代巴比妥酸和醛的Knoevenagel缩合反应。合成方法显示了胶束催化剂对醛活化的优异活性,从而导致容易的缩合。通过进一步合成5,5'-(4-芳基亚甲基)双[二氢-2-硫代-4,6(1H,5H)-嘧啶二酮]证明了该方法的应用。还对该反应进行了理论研究,以研究苯甲醛中电子释放和吸电子基团对反应的影响。

更新日期:2020-12-01
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