The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S8

Liu, Hongyan; Chen, Yu; Hao, Liqiang; Wang, Guodong; Li, Hongshuang; Xia, Chengcai

doi:10.1039/d0ra08441g

RSC Adv.

2020

DOI: 10.1039/d0ra08441g

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The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S₈

Hongyan Liu

Yu Chen

Liqiang Hao

et al.

Abstract: Herein we report an oxidative coupling reaction for N–S/S–S bond formation substituted N,N′-disulfanediyl bis(N′-((E)-benzylidene)acetohydrazide). It provides a direct approach for the synthesis of disulfides with good yields.

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Cited by 4 publications

References 60 publications

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Benzylic C(sp³)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Yavari

Shaabanzadeh

2022

J. Org. Chem.

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The electrooxidation of benzylic C(sp 3 )−H bonds to produce hydrazones as an alternate for conventional pathways has an enormous dignity. Under the aegis of electricity, instead of hazardous metal catalysts and external oxidants, we unveil an electrochemical process for electrooxidation of various benzylic C(sp 3 )−H bonds in aqueous media in all pH ranges that subsequently produce hydrazones with further reactions. This electrooxidative reaction strategy provides an acceptable condition for synthesizing hydrazones with various functional groups in good efficiency and amenable to gram-scale synthesis. The electrochemical oxidation condition proves an excellent level of compatibility with super cheap electrolyte NaCl for the oxidation of benzylic C(sp 3 )−H position despite the highly oxidizable hydrazide group remaining intact in the reaction.

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Benzylic C(sp³)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Yavari

Shaabanzadeh

2022

J. Org. Chem.

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Amination of N-(Organodithio)phthalimides for the Modular Synthesis of Aminodisulfides

Asanuma,

Kanemoto

2023

Org. Lett.

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Synthetic methods for unsymmetrical aminodisulfides are greatly needed due to their applications in drug discovery, linker chemistry, and materials sciences. In this study, an amination reaction of N-dithiophthalimides has been developed for the divergent synthesis of unsymmetrical aminodisulfides. The reaction proceeds under mild conditions and provides the aminodisulfides in excellent yields without cleavage of the disulfide bond. The Ndithiophthalimides are readily available from several bilateral disulfurating reagents, and the broad substrate scope of this reaction allows for the modular synthesis of a variety of unsymmetrical aminodisulfides in two-step operations.

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Access to (E)-N′-benzylidene-N-(2-(phenylsulfonyl)ethyl)acetohydrazide via C(sp²)−H activation and reduction of (E)-N′-benzylideneacetohydrazide with (vinylsulfonyl)benzene

Wang,

Liu

2024

Journal of Chemical Research

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A novel route for C(sp3)-N bond formation via C(sp2)−H activation/reduction by metal-free which uses ( E)- N′-benzylideneacetohydrazide and (vinylsulfonyl)benzene to synthesize derivatives of ( E)- N′-benzylidene- N-(2-(phenylsulfonyl)ethyl)acetohydrazide has been reported. This methodology features good functional group tolerance and convenient operation. In addition, it uses inexpensive and insensitive chemical reagents as raw materials and provides an atom- and efficient method for the preparation of ( E)- N′-benzylidene- N-(2-(phenylsulfonyl)ethyl)acetohydrazides.

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The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S₈

Abstract: Herein we report an oxidative coupling reaction for N–S/S–S bond formation substituted N,N′-disulfanediyl bis(N′-((E)-benzylidene)acetohydrazide). It provides a direct approach for the synthesis of disulfides with good yields.

Cited by 4 publications

References 60 publications

Benzylic C(sp³)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Benzylic C(sp³)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Amination of N-(Organodithio)phthalimides for the Modular Synthesis of Aminodisulfides

Access to (E)-N′-benzylidene-N-(2-(phenylsulfonyl)ethyl)acetohydrazide via C(sp²)−H activation and reduction of (E)-N′-benzylideneacetohydrazide with (vinylsulfonyl)benzene

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The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S8

Abstract: Herein we report an oxidative coupling reaction for N–S/S–S bond formation substituted N,N′-disulfanediyl bis(N′-((E)-benzylidene)acetohydrazide). It provides a direct approach for the synthesis of disulfides with good yields.

Cited by 4 publications

References 60 publications

Benzylic C(sp3)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Benzylic C(sp3)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Amination of N-(Organodithio)phthalimides for the Modular Synthesis of Aminodisulfides

Access to (E)-N′-benzylidene-N-(2-(phenylsulfonyl)ethyl)acetohydrazide via C(sp2)−H activation and reduction of (E)-N′-benzylideneacetohydrazide with (vinylsulfonyl)benzene

Contact Info

Product

Resources

About

The synthesis of N,N′-disulfanediyl-bis(N′-((E)-benzylidene)acetohydrazide) from (E)-N′-benzylideneacetohydrazide and S₈

Benzylic C(sp³)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Benzylic C(sp³)–H Bonds Play the Dual Role of Starting Material and Oxidation Inhibitor for Hydrazides in the Electrochemical Synthesis of Hydrazones

Access to (E)-N′-benzylidene-N-(2-(phenylsulfonyl)ethyl)acetohydrazide via C(sp²)−H activation and reduction of (E)-N′-benzylideneacetohydrazide with (vinylsulfonyl)benzene