Microwave-Accelerated Eco-friendly Performance of the Knoevenagel Condensation Reaction with Various Active Methylene Derivatives-Evaluation of Electrochemical Properties

IF 0.9 Q4 CHEMISTRY, PHYSICAL
Kantharaju Kamanna, Krishnappa B Badiger
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引用次数: 0

Abstract

The present work describes sustainable Knoevenagel condensation reaction of aryl/ heterocyclic aldehyde with various active methylene derivatives such as malononitrile, dimedone, ethyl cyanoacetate, ethyl acetoacetate, barbituric acid, and thiobarbituric acid is reported. The protocol was developed using water extract of mango peel ash (WEMPA), an agro-waste that emerged as a greener solvent media and in combination with microwave irradiation gave high-yield product isolation. The method noticed added advantages for the reaction faster reaction rate, inexpensive extract media, simple work-up, and not required chromatographic purification. The present method synthesized various Knoevenagel condensation derivatives benzylidinemalononitrile, ethyl benzylidenecyanoacetate, ethyl benzylideneacetoacetate, benzalbarbituric acid, benzylidene-2-thiobarbituric acid, and 5,5-dimethylcyclohexane-1,3-diones were characterized by FT-IR, 1H- & 13C-NMR, and mass spectrometry. Further, selected derivatives were investigated for their electrochemical studies using cyclic voltammetry, and showed comparable oxidation and reduction potential properties. The objective of this work is to develop a green methodology synthesis of various active methylene derivatives via Knoevenagel condensation to give the product of benzylidinemalononitrile, ethyl benzylidenecyanoacetate, ethyl benzylideneacetoacetate, benzalbarbituric acid, benzylidene-2-thiobarbituric acid and 5,5-dimethylcyclohexane-1,3-diones. We have demonstrated WEMPA as a greener homogenous agro-waste catalytic medium for the economic synthesis of Knoevenagel condensation products. The developed method was found robust, non-toxic and solvent-free with a simple work-up to give the target product. The selected derivatives were investigated for their electrochemical studies using the cyclic voltammetry method. The agro-waste-based catalyst developed avoids the use of the external organic or inorganic base for the Knoevenagel condensation reaction under microwave irradiation. The described method found faster, eco-friendly, simple filtration and recrystallization excellent yield, and purity of the Knoevenagel product. Further, the selected compounds (8a-8d, 9a- 9d, 10a-10d, 11a,-11c, 12a, 12b, and 13a-13c) were subjected to electrochemical behavior studies and showed good oxidation and reduction properties. In summary, we have established an efficient, simple, inexpensive agro-waste based catalytic approach for the synthesis of benzylidinemalononitrile, ethyl benzylidenecyanoacetate, ethyl benzylideneacetoacetate, benzalbarbituric acid, benzylidene-2-thiobarbituric acid and 5,5-dimethylcyclohexane-1,3-diones derivatives under microwave irradiation described. The catalyst is agro-waste derived, which is abundant in nature and recyclable without loss of activity after the four-run of the reaction, thus making the present approach a greener one. The advantages of the approach are inexpensive, chemical base free, requiring no external metal catalyst, short reaction time, and simple work-up isolated excellent yields of the product. For the first time, herein, we reported the electrochemical behavior of the products prepared, and showed good oxidation and reduction properties, and these molecules will emerge as good antioxidant agents. NA
微波加速与各种活性亚甲基衍生物的Knoevenagel缩合反应的环保性能——电化学性能评价
本文报道了芳基/杂环醛与各种活性亚甲基衍生物如丙二腈、二美酮、氰乙酸乙酯、乙酰乙酸乙酯、巴比妥酸和硫巴比妥酸的持续Knoevenagel缩合反应。该方案是利用芒果皮灰水提取物(WEMPA)开发的,这是一种农业废弃物,作为一种更环保的溶剂介质出现,并与微波辐射相结合,可实现高产量的产品分离。该方法具有反应速度快、提取介质便宜、处理简单、不需要色谱纯化等优点。本方法合成了多种Knoevenagel缩合衍生物苄基二乙烯腈、乙酸乙酯、乙酸乙酯、苯扎巴比妥酸、苄基-2-硫代巴比妥酸、5,5-二甲基环己烷-1,3-二酮,并用FT-IR、1H-和13C-NMR及质谱进行了表征。此外,选择的衍生物用循环伏安法进行了电化学研究,并显示出相当的氧化和还原电位性质。本研究的目的是建立一种绿色的方法,通过Knoevenagel缩合合成各种活性亚甲基衍生物,得到苯并二甲基乙二腈、苯并二甲基乙酯乙酸乙酯、苯并二甲基乙酯乙酸乙酯、苯并巴比妥酸、苯并二甲基-2-硫代巴比妥酸和5,5-二甲基环己烷-1,3-二酮的产物。我们已经证明了WEMPA是一种更环保的均质农业废物催化介质,用于经济合成Knoevenagel缩合产物。所开发的方法被发现是稳健的,无毒的,无溶剂与一个简单的工作,以获得目标产品。用循环伏安法对所选衍生物进行了电化学研究。所研制的农用废弃物基催化剂避免了微波照射下Knoevenagel缩合反应的外部有机或无机碱的使用。该方法快速、环保、过滤和再结晶简单,产品收率高,纯度高。此外,所选化合物(8a-8d, 9a- 9d, 10a-10d, 11a,-11c, 12a, 12b和13a-13c)进行了电化学行为研究,显示出良好的氧化和还原性能。综上所述,我们建立了一种高效、简单、廉价的基于农业废弃物的微波辐射催化合成苄基二甲基戊二腈、苄基二甲基乙酸乙酯、苄基二甲基乙酸乙酯、苯扎巴比妥酸、苄基-2-硫代巴比妥酸和5,5-二甲基环己烷-1,3-二酮衍生物的方法。催化剂来源于农业废弃物,在自然界中含量丰富且可回收,经过四次反应后不会失去活性,因此使本方法更加环保。该方法的优点是价格低廉,无化学碱,不需要外部金属催化剂,反应时间短,加工简单,产品收率高。本文首次报道了所制备产物的电化学行为,并显示出良好的氧化和还原性能,这些分子将成为良好的抗氧化剂。NA
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来源期刊
Current Organocatalysis
Current Organocatalysis CHEMISTRY, PHYSICAL-
CiteScore
2.00
自引率
0.00%
发文量
28
期刊介绍: Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.
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