scholarly journals Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

2020 ◽  
Vol 16 ◽  
pp. 1915-1923 ◽  
Author(s):  
Paola Vitale ◽  
Luciana Cicco ◽  
Ilaria Cellamare ◽  
Filippo M Perna ◽  
Antonio Salomone ◽  
...  
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Environmentally Benign ◽  
Pyrimidine Derivatives ◽  
Reaction Media

We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).

scholarly journals Deep Eutectic Solvents as Smart Cosubstrate in Alcohol Dehydrogenase-Catalyzed Reductions

Catalysts ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1013
Author(s):  
Santiago Nahuel Chanquia ◽  
Lei Huang ◽  
Guadalupe García Liñares ◽  
Pablo Domínguez de María ◽  
Selin Kara
Keyword(s):  
Alcohol Dehydrogenase ◽  
Thermodynamic Equilibrium ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Cofactor Regeneration ◽  
The Novel ◽  
Cinnamyl Alcohol ◽  
Maximum Productivity ◽  
Reaction Media ◽  
Reduction Of Ketones

Alcohol dehydrogenase (ADH) catalyzed reductions in deep eutectic solvents (DESs) may become efficient and sustainable alternatives to afford alcohols. This paper successfully explores the ADH-catalyzed reduction of ketones and aldehydes in a DES composed of choline chloride and 1,4-butanediol, in combination with buffer (Tris-HCl, 20% v/v). 1,4-butanediol (a DES component), acts as a smart cosubstrate for the enzymatic cofactor regeneration, shifting the thermodynamic equilibrium to the product side. By means of the novel DES media, cyclohexanone reduction was optimized to yield maximum productivity with low enzyme amounts (in the range of 10 g L−1 d−1). Notably, with the herein developed reaction media, cinnamaldehyde was reduced to cinnamyl alcohol, an important compound for the fragrance industry, with promising high productivities of ~75 g L−1 d−1.

scholarly journals Reactive Deep Eutectic Solvents (RDESs): A New Tool for Phospholipase D-Catalyzed Preparation of Phospholipids

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 655
Author(s):  
Chiara Allegretti ◽  
Francesco G. Gatti ◽  
Stefano Marzorati ◽  
Letizia Anna Maria Rossato ◽  
Stefano Serra ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Ethylene Glycol ◽  
Phospholipase D ◽  
Choline Chloride ◽  
Reaction Medium ◽  
Deep Eutectic Solvents ◽  
Polar Head ◽  
Process Implementation ◽  
Reaction Media ◽  
Hydrogen Bond Donors

The use of Reactive Deep Eutectic Solvents (RDESs) in the preparation of polar head modified phospholipids (PLs) with phospholipase D (PLD)-catalyzed biotransformations has been investigated. Natural phosphatidylcholine (PC) has been submitted to PLD-catalyzed transphosphatidylations using a new reaction medium composed by a mixture of RDES/buffer. Instead of exploiting deep eutectic solvents conventionally, just as the reaction media, these solvents have been designed here in order to contribute actively to the synthetic processes by participating as reagents. RDESs were prepared using choline chloride or trimethyl glycine as hydrogen-bond acceptors and glycerol or ethylene glycol, as hydrogen-bond donors as well as nucleophiles for choline substitution. Specifically designed RDES/buffer reaction media allowed the obtainment of PLs with optimized yields in the perspective of a sustainable process implementation.

scholarly journals Metal- and solvent-free preparation of benzo[4,5]imidazo[1,2-a]pyrimidine derivatives catalysed by deep eutectic solvents

2021 ◽  
Vol 63 (3) ◽  
pp. 15-17
Author(s):  
Thuy-Duy Thi Nguyen ◽  
◽  
Anh Vy Truong ◽  
Hoang Phuong Tran ◽  
◽  
...  
Keyword(s):  
Ethyl Acetoacetate ◽  
Good Yield ◽  
Choline Chloride ◽  
Biginelli Reaction ◽  
Deep Eutectic Solvent ◽  
Environmentally Friendly ◽  
Deep Eutectic Solvents ◽  
Solvent Free ◽  
Pyrimidine Derivatives ◽  
Solvent Free Conditions

by an acidic deep eutectic solvent from choline chloride (ChCl) and phenol via the Biginelli reaction of 2-aminobenzimidazole, ethyl acetoacetate, and aldehydes has been developed under metal- and solvent-free conditions. The desired products were obtained in moderate to good yield (49-79%) and the DESs were known as an economical and environmentally friendly catalyst.

scholarly journals Lactic Acid Permeation through Deep Eutectic Solvents-Based Polymer Inclusion Membranes

Membranes ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 244
Author(s):  
Michiaki Matsumoto ◽  
Sae Takemori ◽  
Yoshiro Tahara
Keyword(s):  
Lactic Acid ◽  
Transport Mechanism ◽  
Liquid Membrane ◽  
Simple Technique ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Environmentally Benign ◽  
Membrane Process ◽  
Poly Vinyl Chloride ◽  
Simple Preparation

Lactic acid that is prepared by fermentation is a compound in food, cosmetic pharmaceutical, and chemical industries. Since a simple technique is desired that separates lactic acid from the cultures, we propose lactic acid permeation through a poly(vinyl chloride)(PVC)-based membrane that contains deep eutectic solvents (DESs) as a carrier. Lactic acid was successfully permeated through polymer inclusion membranes (PIMs) containing hydrophilic DESs, urea-choline chloride and glucose-choline chloride. The permeation behavior was explained by the facilitated transport mechanism based on the solution-diffusion model. Simple preparation of thinner membranes in the PIM process and higher permeation rates are advantages over the supported liquid membrane process. The PVC-based membrane process containing environmentally benign hydrophilic DESs is promising for lactic acid separation on an industrial scale.

Environmentally Benign Large-Scale Synthesis of a Precursor to Vortioxetine

Synthesis ◽  
2020 ◽  
Vol 52 (18) ◽  
pp. 2662-2666
Author(s):  
John K. Gallos ◽  
Stavroula A. Zisopoulou ◽  
Anastasia E. Pafili ◽  
Petros Gkizis ◽  
Thanos Andreou ◽  
...  
Keyword(s):  
Major Depressive Disorder ◽  
Transition Metal ◽  
Depressive Disorder ◽  
Large Scale ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Environmentally Benign ◽  
Major Depressive ◽  
Metal Free ◽  
High Affinity

An eco-friendly, high-yielding, and transition-metal-free synthesis of 2-[(2,4-dimethylphenyl)thio]aniline precursor to vortioxetine is reported. Vortioxetine, a multi-modal acting drug with high affinity for a range of serotonergic targets, is used for the treatment of major depressive disorder (MDD). The synthesis – applicable in multi-gram scale – involves the reaction of bis(2,4-dimethyl)iodonium bromide with commercial 2-aminophenyl disulfide, whereas its reaction with 2-aminothiophenol afforded the same product but in low to moderate yields. This method works equally well in deep eutectic solvents (DESs), based on choline chloride (ChCl).

scholarly journals Lateral lithiation in deep eutectic solvents: regioselective functionalization of substituted toluene derivatives

2020 ◽  
Vol 56 (16) ◽  
pp. 2391-2394 ◽  
Author(s):  
Davide Arnodo ◽  
Simone Ghinato ◽  
Stefano Nejrotti ◽  
Marco Blangetti ◽  
Cristina Prandi
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Eutectic Mixtures ◽  
Regioselective Functionalization ◽  
Reaction Media

Ultrafast heteroatom-directed lateral lithiation of substituted toluene derivatives using choline chloride-based eutectic mixtures as bio-inspired sustainable reaction media.

scholarly journals Tunable and functional deep eutectic solvents for lignocellulose valorization

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yongzhuang Liu ◽  
Noemi Deak ◽  
Zhiwen Wang ◽  
Haipeng Yu ◽  
Lisanne Hameleers ◽  
...  
Keyword(s):  
Ethylene Glycol ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Enzymatic Digestion ◽  
High Yield ◽  
Good Efficiency ◽  
Biomass Processing ◽  
Lignin Condensation ◽  
Biomass Fractionation ◽  
Reaction Media

AbstractStabilization of reactive intermediates is an enabling concept in biomass fractionation and depolymerization. Deep eutectic solvents (DES) are intriguing green reaction media for biomass processing; however undesired lignin condensation is a typical drawback for most acid-based DES fractionation processes. Here we describe ternary DES systems composed of choline chloride and oxalic acid, additionally incorporating ethylene glycol (or other diols) that provide the desired ‘stabilization’ function for efficient lignocellulose fractionation, preserving the quality of all lignocellulose constituents. The obtained ethylene-glycol protected lignin displays high β-O-4 content (up to 53 per 100 aromatic units) and can be readily depolymerized to distinct monophenolic products. The cellulose residues, free from condensed lignin particles, deliver up to 95.9 ± 2.12% glucose yield upon enzymatic digestion. The DES can be recovered with high yield and purity and re-used with good efficiency. Notably, we have shown that the reactivity of the β-O-4 linkage in model compounds can be steered towards either cleavage or stabilization, depending on DES composition, demonstrating the advantage of the modular DES composition.

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

Self-assembled luminescent cholate gels induced by a europium ion in deep eutectic solvents

Soft Matter ◽  
2021 ◽  
Author(s):  
Meng Sun ◽  
Qintang Li ◽  
Xiao Chen
Keyword(s):  
Self Assembly ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Sodium Cholate ◽  
The Self ◽  
Europium Ion ◽  
Self Assembled

Luminescent gels have been successfully fabricated through the self-assembly of sodium cholate and a europium ion in choline chloride-based deep eutectic solvents.

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