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  • 72 Reads
Ternary mixtures of N-butyl-pyrrolidinium bis(trifluoromethanesulfonyl)imide, lithium bis(trifluoromethanesulfonyl)imide and carbonate as advanced electrolytes for lithium-ion batteries

The electrochemical energy storage plays a crucial role towards the decarbonisation of the electricity sector by improving the integration and exploitation of renewable energy sources.

Commercially available electrolytes for lithium-ion batteries are based on organic carbonates with lithium salts, offering good electrical conductivities although, as organic solvents are volatile and highly flammable, limiting the safety of these devices. During the last years smart new electrolytes based on mixtures of ionic liquids (ILs) with inorganic salts have been proposed with regards to their good electrical properties, good thermal and chemical stabilities and low toxicity.

In this work, thermophysical properties of the ternary liquid mixtures IL + lithium salt + carbonate were studied in terms of thermal transition temperatures, thermal stability and electrical conductivity of mixtures against pure compounds. The selected ionic liquid is the N-butyl-pyrrolidinium bis(trifluoromethanesulfonyl)imide; the lithium salt with common anion, lithium bis(trifluoromethanesulfonyl)imide salt and two different carbonates (dimethyl carbonate or diethyl carbonate) were used to prepare the ternary mixtures.

The main results observed were the cryoscopic decrease in IL with the salt addition, a reduction of crystallinity of ternary mixtures with regards to pure IL and IL+salt samples and the electric conductivity of mixtures, which increase with increasing temperature, presented a maximum for xcarbonate=0.6 and decrease with the increasing chain length of carbonate.

  • Open access
  • 48 Reads
Synthesis of N-(hydroxymethylene)thioamides by N- hydroxymethylation of 2-cyanothioacrylamides

The condensation products of cyanothioacetamide with aldehydes – (E)-arylmethylenyanothioacetamides – have proven to be readily available and multifunctional starting reagents in the chemistry of S,N-containing compounds. We decided to study the interaction of formaldehyde with thioamides as a possible way to obtain N-(hydroxymethylene)thioamides are promising thioamidoalkylating agents and new ligands for complexation. It was found that the reaction of thioamides and formaldehyde proceeds easily when the reagents are heated in the absence of catalysts in an aqueous-alcohol medium, and leads with good yields to the expected N-(hydroxymethylene)thioamides. Structure of N-(hydroxymethylene)thioamides 2 was confirmed by IR and NMR spectroscopy data.

  • Open access
  • 69 Reads
Synthesis of new highly functionalized nicotinic acids
, , ,

2,2-Dimethyl-5-((phenylamino)methylene)-1,3-dioxane-4,6-dione, prepared by ternary condensation of Meldrum’s acid with triethyl orthoformate and aniline, reacts with cyanoacetic acid hydrazide in the presence of KOH to give 1-amino-5-cyano-2-oxo-1,2-dihydropyridine-3-carboxylic acid, which is useful as drug precursors or perspective ligands.

  • Open access
  • 41 Reads
Synthesis of kinase inhibitors utilizing thiophile-free Eschenmoser reaction of bromoindol-2-ones and thioamides
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In the past two decades, compounds with 3-[phenylamino(phenyl)methylidene]indol-2-one pharmacophore have been estabilished in the treatment of several autoimmune diseases and diverse malignancies.

Despite extraordinary medicinal interest, synthetic accesibility of compounds with this structure moiety is somewhat limited. Most of commercial synthetic routes use condensation of protected 3-[alkoxy(phenyl)methylidene]indol-2-ones with anilines as key reaction step.

Recently, we found that the chemical transformation of thioiminium salts derived from 3-bromoindol-2-ones and thioamides can involve Eschenmoser reaction under specific conditions. Our recent findings have confirmed that this reaction could serve as a powerfull tool in synthesis of 3-[amino(phenyl)methylidene]indol-2-ones.

In this work, we would like to further demonstrate the usefulness of our novel synthetic approach for the preparation of some well-known molecules, especially Nintedanib and Hesperadin, which act as potent tyrosine or Aurora A/B kinase inhibitors.

The Eschenmoser sulfide contraction of subst. 3-bromoindol-2-ones with thiobenzanilide derivatives proceeded smoothly in highly polar aprotic solvents and provided the desired indol-2-ones in good to excellent yields.

  • Open access
  • 54 Reads
Quantitative Analysis of total phenolic and flavonoid contents from Stachys mouretii leaves extracts

Stachys mouretii leaves extracts were analyzed for total phenolic and flavonoid contents. These components are responsible for antioxidant activity. The plant material was collected in April 2018 at the forest of Talasemtane in the region of Ouazzane, Morocco. Dried and crushed leaves were subjected to sequential extraction with hexane, ethyl acetate, and methanol in order of increasing polarity. The amount of total phenolic and flavonoids were determined with the Folin-Ciocalteu and aluminum chloride (AlCl3) reagents respectively. For the total phenolic, gallic acid was used as a standard compound and the results were expressed as µg/mL gallic acid equivalent (GAE). While for the total flavonoids, quercetin was used as a standard compound and the results were expressed as mg/mL quercetin equivalent (QE). The total phenolic content of Stachys mouretii leaves extracts varied from 14.13 to 26.91 µg/mL GAE and the total flavonoids content ranges from 0.04 to 0.08 mg/mL QE. The maximum phenolic and flavonoids contents were found in the ethyl acetate extract. The findings suggested that phytochemicals present in Stachys mouretii are potentially beneficial as therapeutic and antioxidative agents in pharmaceuticals, food, and other related industries.

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