In Situ Generated Cetyltrimethylammonium Bisulphate in Choline Chloride–Urea Deep Eutectic Solvent: A Novel Catalytic System for One Pot Synthesis of 1,3,4-Oxadiazole

More, Priyanka A.; Gadilohar, Balu L.; Shankarling, Ganapati S.

doi:10.1007/s10562-014-1288-3

Cited by 17 publications

(6 citation statements)

References 30 publications

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“…The recyclability of the reaction media was also studied and, although the yields still remained high, appreciable erosion of the results were observed after four consecutive reaction cycles. [107] . N-arylphthalimides were also straightforwardly synthesized in high yields by the condensation between phthalic anhydride and anilines in a ChCl-urea mixture (1:2 molar ratio) at 80 ºC.…”

Section: Condensation Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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This microreview summarizes the use of deep eutectic solvents (DES) and related melts in Organic Synthesis. This type of solvents combine the great advantages of other proposed environmentally benign alternative solvents, such as low toxicity, high availability, low inflammability, high recyclability, low volatility and low price, avoiding many disadvantages of these neoteric media. The fact that many of the components of the mixture come directly from Nature assures their biodegradability and renewability. The classification and distribution of the reactions in different sections along this microreview, as well as the emphasis paid to their scope, easily allows a general reader to understand the actual state of art, and the great opportunities opened, not only for academic proposes but also for industry.

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Section: Condensation Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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“…[ 3 , 4 , 5 ]. Their application in organic synthesis includes synthesis of different heterocycles [ 6 , 7 , 8 , 9 , 10 ], esterification [ 11 ], aldol reactions [ 12 ], halogenation [ 13 ] as well as N -acetylation of amines [ 14 ], synthesis of mercapto quinazolinones [ 15 ], and Schiff bases [ 16 ], all performed by our group. Knoevenagel condensation in deep eutectic solvents has been studied by Keshavarzipour and Tavakol [ 17 ], indicating that DESs could be a very useful tool in this type of condensation.…”

Section: Introductionmentioning

confidence: 99%

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

et al. 2018

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A series of rhodanine derivatives was synthesized in the Knoevenagel condensation of rhodanine and different aldehydes using choline chloride:urea (1:2) deep eutectic solvent. This environmentally friendly and catalyst free approach was very effective in the condensation of rhodanine with commercially available aldehydes, as well as the ones synthesized in our laboratory. All rhodanine derivatives were subjected to 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging activity investigation and quantitative structure-activity relationship (QSAR) studies were performed to elucidate their structure-activity relationship. The best multiple linear QSAR model demonstrate a stability in the internal validation and Y-randomization (R2 = 0.81; F = 24.225; Q2loo = 0.72; R2Yscr = 0.148). Sphericity of the molecule, ratio of symmetric atoms enhanced atomic mass along the principle axes in regard to total number of atoms in molecule, and 3D distribution of the atoms higher electronegativity (O, N, and S) in molecules are important characteristic for antioxidant ability of rhodanine derivatives. Molecular docking studies were carried out in order to explain in silico antioxidant studies, a specific protein tyrosine kinase (2HCK). The binding interactions of the most active compound have shown strong hydrogen bonding and van der Waals interactions with the target protein.

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“…Generally peroxydisulfate decomposes to bisulphate (Eq.1-3) in presence of water via sulphate anion radical formation 48,49 Table 3, ChPS appears to encourage the reaction more effectively than a number of other catalysts, even ILs mostly in terms of use of the starting material i.e. In our TSIL system, the peroxydisulfate anion and choline cation may be a possible participant in the reaction.…”

Section: Thio-betti Basesmentioning

confidence: 88%

“…The co-existence of peroxydisulfate and the hydrogen bonding donors of choline are perhaps the main reason for the high oxidising activity of the TSIL. In general, peroxydisulfate decomposes to bisulphate (eqn (1)-( 3)) in the presence of water via sulphate anion radical formation 48,49 (eqn (1)). Similarly, 1 decomposes in the presence of water to give 2 ([Ch] + HSO 4 À ) by evolving oxygen.…”

Section: Plausible Mechanism For the Oxidant And Catalytic Activity O...mentioning

confidence: 99%

Choline peroxydisulfate oxidizing Bio-TSIL: triple role player in the one-pot synthesis of Betti bases and gem-bisamides from aryl alcohols under solvent-free conditions

2015

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ARTICLE This journal isOne pot, multicomponent solvent free synthesis of Betti bases (amidoalkyl naphthols) and gem-bisamides directly from alcohol is proposed by an eco-friendly approach using new environmentally benign biodegradable oxidizing task specific ionic liquid (bio-TSIL), Choline peroxydisulfate monohydrate (ChPS) 1. Choline bisulphate (ChBS) 2 reduced species is generated in situ from 1, which catalyses formation of desired products in shorter reaction time, with good to excellent yields. This bio-TSIL 1 plays triple role as oxidant, catalyst and solvent. It was easily recycled and reused for five times.

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In Situ Generated Cetyltrimethylammonium Bisulphate in Choline Chloride–Urea Deep Eutectic Solvent: A Novel Catalytic System for One Pot Synthesis of 1,3,4-Oxadiazole

Cited by 17 publications

References 30 publications

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

Choline peroxydisulfate oxidizing Bio-TSIL: triple role player in the one-pot synthesis of Betti bases and gem-bisamides from aryl alcohols under solvent-free conditions

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