Electrode instead of catalyst and enzyme. A greener protocol for the synthesis of new 2-hydroxyacetamide derivatives containing a γ-lactone ring

Maleki, Abbas; Nematollahi, Davood; Rasouli, Fereshteh; Zeinodini-Meimand, Azam

doi:10.1039/c5gc01863c

Cited by 12 publications

(9 citation statements)

References 42 publications

(12 reference statements)

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“…674 Catechols and related derivatives constitute another class of compounds that can undergo two-electron anodic oxidation to afford, for example, 1,2-benzoquinones. [675][676][677][678][679][680][681] Considering their relatively low oxidation potentials, it is perhaps unsurprising that an assortment of nucleophiles are compatible with these processes without being subjected to oxidation. Here, amines, [682][683][684][685][686][687][688][689] azide, 690,691 enolates and other carbon nucleophiles, [692][693][694][695][696][697][698][699][700][701][702][703][704][705][706][707][708][709][710][711] nitrate, 712 sulfinates [713][714][715][716][717][718][719][720]…”

Section: Electrochemical Oxidative Cross-couplingsmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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Section: Electrochemical Oxidative Cross-couplingsmentioning

confidence: 99%

Electrochemical strategies for C–H functionalization and C–N bond formation

2018

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“…32 In addition, the proven efficacy of AgSD in the treatment of Pseudomonas infection in burns has been documented. 33 In line with our research program in replacing traditional synthetic methods by electrochemical methods [1][2][3][4][5][6][7]17 herein, we would like to report an efficient electrochemical method for the synthesis of AgSD microcrystals through oxidation of a silver rod in the presence of sulfadiazine in aqueous solution and in a simple quasi-two-compartment cell.…”

Section: Introductionmentioning

confidence: 99%

Green electrochemical synthesis of silver sulfadiazine microcrystals

2019

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Electrochemical synthesis of silver sulfadiazine (AgSD) microcrystals was carried out galvanostatically in a special two-electrode cell equipped with a sacrificial silver rod anode and a stainless steel plate cathode. The cell used in this work consists of a small cylindrical chamber containing aqueous sulfadiazine/sodium nitrate as the anode compartment inside a larger cylindrical chamber containing nitric acid solution as the cathode compartment.The ionic connection of two chambers is carried out through a solvent surface layer. In this study, the effect of the experimental parameters such as applied current density and sodium nitrate concentration as well as nitric acid concentration on the yield and energy consumption of AgSD is discussed. The proposed method is fast and green and has unique features including synthesis in a single step, and no need for a metal salt.

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“…We have been able to develop this feature and use it in some syntheses. [18][19][20][21] Electrochemical methods are also the best option for the synthesis of metal complexes. 22 Using these methods, inorganic and organic metal complexes can be directly synthesized.…”

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confidence: 99%

Green Electrochemical Complexation of Fluconazole, Itraconazole, Voriconazole, Ketoconazole and Clotrimazole with Silver, Copper and Zinc Cations

Godini,

Nematollahi,

Zivari-Moshfegh

2023

J. Electrochem. Soc.

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Electrochemical complexation of azole antifungal drugs fluconazole, itraconazole, ketoconazole, voriconazole, and clotrimazole with silver, copper, and zinc cations was carried out galvanostatically in an undivided electrolytic cell equipped with a sacrificial anode under green conditions. In this work, we synthesized 20 different complexes of these drugs by a simple method in water (containing a strong acid)/ethanol mixtures with high yield (average 67%) and purity. The effective synthetic parameters, including the applied current, electricity consumption, acid concentration, cell voltage, energy consumption, and cell design were optimized. Our results indicate that the applied current and acid concentration have no significant effects on the yield and purity of azole complexes. But these factors have a significant effect on cell voltage and energy consumption in such a way that by increasing the applied current or decreasing the acid concentration, the cell voltage and energy consumption increase. Fourier transform infrared spectroscopy, field-emission scanning electron microscopy and energy-dispersive X-ray techniques have been used for the characterization of synthesized complexes. In addition, cyclic voltammetry analysis has been used to investigate the reaction mechanism. This method provides an efficient and green strategy for the complexation of azole drugs in one step without the need for metal salts.

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Electrode instead of catalyst and enzyme. A greener protocol for the synthesis of new 2-hydroxyacetamide derivatives containing a γ-lactone ring

Abstract: Electrochemical synthesis of novel 2-hydroxyacetamides was performed in a one-pot protocol including the oxygen activation, extradiol cleavage, lactonization and amide bond formation sequence without any catalyst and enzyme.

Cited by 12 publications

References 42 publications

Electrochemical strategies for C–H functionalization and C–N bond formation

Electrochemical strategies for C–H functionalization and C–N bond formation

Green electrochemical synthesis of silver sulfadiazine microcrystals

Green Electrochemical Complexation of Fluconazole, Itraconazole, Voriconazole, Ketoconazole and Clotrimazole with Silver, Copper and Zinc Cations

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