Microwave-Accelerated Eco-friendly Performance of the Knoevenagel Condensation Reaction with Various Active Methylene Derivatives-Evaluation of Electrochemical Properties
{"title":"Microwave-Accelerated Eco-friendly Performance of the Knoevenagel Condensation Reaction with Various Active Methylene Derivatives-Evaluation of Electrochemical Properties","authors":"Kantharaju Kamanna, Krishnappa B Badiger","doi":"10.2174/2213337210666230228103824","DOIUrl":null,"url":null,"abstract":"\n\nThe 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.\n\n\n\nThe 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.\n\n\n\nWe 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.\n\n\n\nThe 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.\n\n\n\nIn 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.\n\n\n\nNA\n","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":null,"pages":null},"PeriodicalIF":0.9000,"publicationDate":"2023-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Organocatalysis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/2213337210666230228103824","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
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.
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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.