Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

Singh, Sushma; Sharma, Laxmi Kant; Saraswat, Apoorv; Siddiqui, I. R.; Singh, R. K. P.

doi:10.1007/s11164-012-1013-z

Cited by 14 publications

(7 citation statements)

References 47 publications

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“…Tabakovic and Gunic later reported on the indirect electrosynthesis of 2-amino-5-(3-methoxy-4-benzyloxy)phenyl-1,3,4-oxadiazole using an organic mediator . Similar work has been reported within the past decade by Singh et al on a variety of substituted semicarbazones. , These electrolysis reactions were performed in acetonitrile using a Pt anode, a Pt cathode, and a 0.1 M LiClO 4 electrolyte.…”

Section: Nitrogen-rich Heterocycle Formationmentioning

confidence: 65%

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Electrochemical Synthesis of High-Nitrogen Materials and Energetic Materials

Yount

Piercey

2022

Chem. Rev.

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Electrochemical synthesis is a valuable method for the preparation of molecules. It is innately eco-friendly, as potentially hazardous oxidation and reduction agents are replaced with electrochemical potentials. Electrochemistry is commonly applied globally in the synthesis of numerous chemicals, but the energetic materials field lags in this regard. In this review, we endeavor to cover the entire history of synthetic electrochemistry for the preparation of energetic materials and detail the electrochemical transformations of high-nitrogen materials that are relevant for the preparation of new energetic molecules. We hope this review serves as a starting point to inform those involved in synthetic energetic materials chemistry, and those interested in other applications of high-nitrogen molecules, about the environmentally friendly electrochemical methods available for such compounds.

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Section: Nitrogen-rich Heterocycle Formationmentioning

confidence: 65%

“…172 Similar work has been reported within the past decade by Singh et al on a variety of substituted semicarbazones. 173,174 These electrolysis reactions were performed in acetonitrile using a Pt anode, a Pt cathode, and a 0.1 M LiClO 4 electrolyte.…”

Section: N Heterocyclesmentioning

confidence: 94%

Electrochemical Synthesis of High-Nitrogen Materials and Energetic Materials

Yount

Piercey

2022

Chem. Rev.

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“…Compared with classical organic transformations, electrosynthesis normally can be run under mild reaction conditions and electrons can be deemed as a traceless reagent which results in the advantage that no stoichiometric oxidant or reductant is needed. Singh and co‐workers reported the synthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles based on the electrochemical oxidation of aldehyde‐ N ‐arylhydrazones under ambient conditions . Considering the rich reactivity of α‐keto acids, they have been employed extensively under electrochemical conditions in recent years .…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Synthesis of 2,5‐Disubstituted 1,3,4‐Oxadiazoles from α‐Keto Acids and Acylhydrazines Under Mild Conditions

Gong

et al. 2020

Eur J Org Chem

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1,3,4‐Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α‐keto acids and acylhydrazines has been developed for the synthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5‐disubstituted 1,3,4‐oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.

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“…This molecule is a derivative of nitrofuran, which has strong antibacterial activity [20]. , Raltegravir [98], Nesapidil [99], Zibotentan [95], Thiodazosin [97].…”

Section: 34-oxadiazoles Used Commercially In Agriculture and Medicinementioning

confidence: 99%

Synthesis and Biological Activity of 1,3,4-Oxadiazoles Used in Medicine and Agriculture

Łuczyński

Kudelko

2022

Applied Sciences

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Biologically active compounds play a key role in the fight against diseases affecting both human and animal living organisms, as well as plants. Finding out about new molecules with a potential biological effect, not yet described in the literature, is one of the most important aspects in the development of medicine and agriculture. Compounds showing desirable biological activity include heterocyclic moieties such as 1,3,4-oxadiazoles. The oxadiazole molecule is composed of two nitrogen atoms and one oxygen atom, forming a five-membered heterocyclic ring. Structures of this type have been successfully used in the treatment of various diseases in humans and animals, and play an important role in modern agriculture. It has been proven that many oxadiazole derivatives exhibit antibacterial, antiviral, blood pressure lowering, antifungal, antineoplastic, anticancer, antioxidant, anti-inflammatory and analgesic properties. In addition, compounds based on 1,3,4-oxadiazole can act as plant protection agents due to their herbicidal, insecticidal and fungicidal activity. Due to the constantly growing interest in heterocyclic systems of this nature, new methods of obtaining complex structures containing oxadiazole rings are sought. This article discusses various methods of synthesis of 1,3,4-oxadiazole derivatives exhibiting biological activity. Based on these techniques, these compounds could be used in the future in medicine and agriculture.

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Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

Cited by 14 publications

References 47 publications

Electrochemical Synthesis of High-Nitrogen Materials and Energetic Materials

Electrochemical Synthesis of High-Nitrogen Materials and Energetic Materials

Electrochemical Synthesis of 2,5‐Disubstituted 1,3,4‐Oxadiazoles from α‐Keto Acids and Acylhydrazines Under Mild Conditions

Synthesis and Biological Activity of 1,3,4-Oxadiazoles Used in Medicine and Agriculture

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