An Efficient Synthesis of Symmetrical Bisamides Catalysed by Molecular iodine under Neutral Conditions

Wang, Hongshe; Zeng, June

doi:10.3184/174751912x13383107316656

Cited by 6 publications

(4 citation statements)

References 21 publications

(21 reference statements)

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“…The quantity of I 2 in the mixture and the synthesis time were varied in the experiments. The use of I 2 as the catalyst for the reaction between carboxamides and aldehydes was described earlier …”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Diaminoacetic Acid Derivatives as a Promising Scaffold for the Synthesis of Polyheterocyclic Cage Compounds

Paromov

Sysolyatin

2021

ACS Omega

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Here, we explored in detail an acid-catalyzed condensation of glyoxylic acid or its ethyl ester with several carboxamides of different basicity, or with mesyl amide, to furnish diaminoacetic acid derivatives. The most suitable synthesis conditions and the reaction catalysts were identified. Properties such as structure and basicity of the starting amides were demonstrated to influence the condensation process. Elemental iodine was used for the first time herein as an acid catalyst for the condensation of glyoxylic acid or its ester, which gave access to diaminoacetic acid derivatives in higher yields in most cases, as opposed to p-toluenesulfonic acid (PTSA). An abnormally high activity of mesyl amide when condensed with ethyl glyoxylate was noticed, which may evidence a special impact of the sulfonyl moiety in the amide molecule on the condensation.

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Section: Resultsmentioning

confidence: 99%

“…The use of I 2 as the catalyst for the reaction between carboxamides and aldehydes was described earlier. 27 Table 3 lists data on the most favorable conditions for the formation of compounds 2a−i from the I 2 -catalyzed condensation between the selected amides and glyoxylic acid or ethyl glyoxylate in toluene under reflux.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of Diaminoacetic Acid Derivatives as a Promising Scaffold for the Synthesis of Polyheterocyclic Cage Compounds

Paromov

Sysolyatin

2021

ACS Omega

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“…The innovation in our approach lies in adopting a condensation reaction between aryl amide and aryl aldehyde to form a novel bifurcated linkage termed dibenzamide (DBA) . This method not only introduces a non-nucleophilic amide as a nucleophile, resulting in dibenzamide (DBA)-based molecules but also overcomes the limitations of amide not being directly used as a building unit in designing amide-functionalized POPs. , This anticipation led to the design and synthesis of a series of porous polybenzamides through the condensation reaction between terephthalamide (TAm) and terephthalaldehyde (TA).…”

Section: Introductionmentioning

confidence: 99%

Lithiophilic Dibenzamide Linkages to Impart Lithium Storage Capacity in Porous Polybenzamides

Karak,

Singh,

Biswas

et al. 2024

J. Am. Chem. Soc.

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Polymer-based organic cathode materials have shown immense promise for lithium storage, owing to their structural diversity and functional group tunability. However, designing appropriate high-performance cathode materials with a high-rate capability and long cycle life remains a significant challenge. It is quintessential to design polymer-based electrodes with lithiophilic linkages. Herein, we design a bifurcated dibenzamide (DBA) linkage having lithiophilic functionalities. 1 H NMR has been used as an experimental tool to understand the lithiophilic nature of the DBAs. Considering the strong Li + affinity of DBAs, a series of polybenzamides have been designed as lithium storage systems. The design of porous polybenzamides consists of amides as only redox-active functionalities, and the rest are inactive phenyl units. Porous polybenzamides, when tested as cathodes against a Li-metal anode, displayed high capacity and rate performance, demonstrating their redox activity. The most efficient polybenzamide (TAm-TA) delivered a specific capacity of 248 mA h g −1 at 1C. TAm-TA retained 63% of its specific capacity at a very high rate of 10C (157 mA h g −1 ). Notably, polybenzamides displayed a capacity enhancement during long cycling, tending to achieve their theoretical capacity. Long cycling stability tests over 3000 cycles at a rate of 1.3C and over 6000 cycles at elevated rates (5C to 40C) demonstrate the electrochemical robustness of dibenzamide linkages. Finally, two full-cell experiments using TAm-TA as both cathode and anode were conducted, which delivered high capacity, demonstrating that TAm-TA is a promising candidate for Li + -ion batteries (LIBs). Furthermore, the ex situ Fourier transform infrared (FT-IR), X-ray photoemission spectroscopy (XPS), and density functional theory (DFT) studies revealed the stepwise lithiation/delithiation mechanism for polybenzamides.

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“…[21][22][23][24][25] Therefore, considering a vast variety of applications of bisamides in diverse areas of science and technology, in recent years, numerous synthetic methods have been developed either with the usage of catalyst or an activator. [26][27][28][29][30][31] Despite many advantages, these conventional methodologies suffer with one or more drawbacks, like involvement of hazardous volatile organic solvents, harsh reaction conditions, corrosive as well as expensive acid catalysts, longer reaction time and lower yields in some of the cases. Not surprisingly, the insolubility issue of bisamides in common organic solvents makes the separation of desired products from the reaction mixture a daunting task and hence leads to tedious work-up procedure.…”

Section: Introductionmentioning

confidence: 99%

Investigating the Role of Natural Deep Eutectic Low Melting Mixtures for the Synthesis of Symmetrical Bisamides

Rather

Ali

2021

ChemistrySelect

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Keeping in view the fundamental significance of bisamides in nature, medicine, and biological systems in addition to their utility in chemistry of synthons, there is a tremendous need to develop environmentally benign synthetic methodologies for the construction of bisamides and their congeners. Herein, for the first time, we report a green and highly efficient method for the synthesis of diverse symmetrical bisamides in good to excellent yields through the condensation of diverse aromatic aldehydes with amides under operationally simple reaction conditions. The present strategy involves a renewable, biode-gradable, and reusable, natural deep eutectic mixture of choline chloride and L-(+)-tartaric acid in the ratio of 2 : 1 at 100 °C for the generation of a range of bisamides. Moreover, we have fruitfully assembled diverse urea-based symmetrical bisamides with the usage of a low melting mixture of L-(+)-tartaric and urea (1 : 4) in decent yields. On large scale synthesis, both the methods were also found to be quite effective which leads to the formation of desired bisamides without significant decrease in the yields, thereby revealing their significance from industrial as well as academic viewpoint.

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An Efficient Synthesis of Symmetrical Bisamides Catalysed by Molecular iodine under Neutral Conditions

Abstract: An efficient synthesis of symmetrical bisamides is described in which aldehydes are reacted with amides in the presence of 5 mol% of iodine to give the corresponding bisamides in high yields under neutral conditions.

Cited by 6 publications

References 21 publications

Synthesis of Diaminoacetic Acid Derivatives as a Promising Scaffold for the Synthesis of Polyheterocyclic Cage Compounds

Synthesis of Diaminoacetic Acid Derivatives as a Promising Scaffold for the Synthesis of Polyheterocyclic Cage Compounds

Lithiophilic Dibenzamide Linkages to Impart Lithium Storage Capacity in Porous Polybenzamides

Investigating the Role of Natural Deep Eutectic Low Melting Mixtures for the Synthesis of Symmetrical Bisamides

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