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Search for "water" in Full Text gives 2191 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Electrochemical allylations in a deep eutectic solvent

  • Sophia Taylor and
  • Scott T. Handy

Beilstein J. Org. Chem. 2024, 20, 2217–2224, doi:10.3762/bjoc.20.189

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  • constant current conditions with sacrificial tin electrodes resulted in 50% conversion to the allylation product and starting material after passing 2.5 F/mol of current. This poor conversion could be significantly improved by adding 10 volume percent of water to the reaction mixture, which also visibly
  • decreased the viscosity. While complete conversion was still not achieved (67% conversion), it was a considerable improvement. Using glassy carbon electrodes with two equivalents of tin(II) chloride under a constant potential of 2 V, but still in CC/EG with 10 volume percent water, resulted in further
  • recycling (Table 8). As with TBAB/EG, the allylation of p-anisaldehyde with allyl bromide was conducted using 2 equivalents of tin(II) chloride in CC/EG with 10 volume percent water at a constant potential of 2 V until 2.5 F/mol of current had been passed through the reaction. The product and unreacted
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Published 02 Sep 2024

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

  • Shakeel Alvi and
  • Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

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  • to a mixture of 60 mL acetic acid and 30 mL concentrated HCl, then the reaction mixture was stirred for 16 h at 100 °C. The creamy precipitate (4.7 g, 80%) was obtained after pouring the reaction mixture into crushed ice, washed with water, acetone and dichloromethane (DCM), then dried under vacuum
  • atmosphere. The flask was cooled to 0 ºC, and stirred vigorously after that n-BuBr (11.30 mL, 105.12 mmol) was slowly added to the RB-flask, and the mixture was stirred for 24 h at room temperature (rt), until the reaction completed (TLC monitoring). Then the reaction mixture was quenched with water, and the
  • crude product was extracted with ethyl acetate. The combined organic layers were washed with water (2 × 100 mL), dried over anhydrous Na2SO4. After evaporation of the solvent the residue was passed through a silica gel (SiO2) to give the final product as a white powder (7.5 g, 95%). The 1H NMR spectrum
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Published 29 Aug 2024

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

  • Kateryna V. Dil and
  • Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

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  • , was found to be 67–129 Å2 for all compounds except products 4 and 2e. None of the compounds penetrate the BBB (blood–brain barrier) except for seleno-2p and desulfurized product 7. Regarding water solubility, we can conclude that all compounds are either soluble or moderately soluble. For more details
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Published 27 Aug 2024

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

  • Zsuzsanna Fehér,
  • Dóra Richter,
  • Gyula Dargó and
  • József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

Graphical Abstract
  • and changes in the reaction kinetics. The non-covalent immobilisation of chiral organocatalysts can also be carried out within deep eutectic solvents (DESs). Very recently, a cinchonidine-squaramide organocatalyst was immobilised in three types of natural DESs, namely betaine/sorbitol/water, betaine
  • /xylitol/water, and betaine/mannitol/water [74]. In these systems, the recyclability of the organocatalyst was investigated and several reaction cycles were performed using the same DESs and organocatalyst. For example, in the Michael addition of methyl 2-oxocyclopentane-1-carboxylate and trans-β
  • -nitrostyrene, the recyclability of the organocatalyst in the betaine/sorbitol/water DES system was demonstrated up to 10 cycles without any significant decrease in yield (up to 99%) or stereoselectivity (up to 96% ee). Encapsulation is an irreversible method and the only catalyst immobilisation process that
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Published 26 Aug 2024

Computational toolbox for the analysis of protein–glycan interactions

  • Ferran Nieto-Fabregat,
  • Maria Pia Lenza,
  • Angela Marseglia,
  • Cristina Di Carluccio,
  • Antonio Molinaro,
  • Alba Silipo and
  • Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

Graphical Abstract
  • interface, and a wide range of analysis tools for studying complex biomolecular systems. AMBER provides various force fields, specifically optimised for simulating biological molecules, as lipids (lipids21) [57], proteins (ff14SB) [58], water molecules (TIP3P) [59], general organic molecules (gaff2) [60
  • ) sample the glycan conformational space; ii) investigate how the glycan behaves in a solution (if the MD is performed in explicit solvent), describing carbohydrate–water interactions; iii) monitoring the intramolecular interactions. Usually, this information has to be further validated by performing
  • , water network prediction, and 3D-QSAR. GRID 2021 introduced a new interface aimed at structure-based design. It enables users to explore binding sites using classic GRID MIFs, encompassing 74 different chemical types. Additionally, it offers a new molecular probe for generating MIFs specific to
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Published 22 Aug 2024

Cage-like microstructures via sequential Ugi reactions in aqueous emulsions

  • Rita S. Alqubelat,
  • Yaroslava A. Menzorova and
  • Maxim A. Mironov

Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179

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  • redissolution in water resulted in colloidosomes with large holes on the surface. Varying the cross-link density during the Ugi reaction made it possible to obtain structures with different hole sizes. Keywords: carboxymethylcellulose; chitosan; colloidosomes; Pickering emulsions; Ugi reaction; Introduction
  • emulsions. The polystyrene particles were treated with sulfuric acid to form a surface layer of sulfonated polystyrene. These particles were then used to produce Pickering emulsions, which were transformed into large-pore structures when treated with an alcohol/water mixture [12]. Another method involves
  • polysaccharides [18]. Therefore, to stabilize such structures, the Ugi reaction in water was chosen, for which this particular pH value range is optimal [19]. The amino groups of chitosan and the carboxy groups of CMC reacted with each other and formed a stable structure that was no longer sensitive to changes in
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Published 22 Aug 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

Graphical Abstract
  • -hydroxypyrazoles 143 and not tautomeric 3-pyrazolones. Alternative access to alkynones can be achieved by nucleophilic addition of lithiated alkynes to N-substituted phthalimides 145, followed by ring opening to give, upon the addition of water, the corresponding 3-hydroxyindolines. These intermediates are in
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Published 16 Aug 2024

Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

  • Beatrice E. Jones,
  • Camille Blayo,
  • Jake L. Greenfield,
  • Matthew J. Fuchter,
  • Nathan Cowieson and
  • Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

Graphical Abstract
  • lipid tail length in the Z isomer [26]. Notably, these authors observed that the X-rays themselves also induced Z–E isomerisation in Azo-lipids, which they attributed to the X-ray radiolysis of water, which produces radicals and reactive species that can catalyse Z–E conversion [27]. This effect was
  • greater using low-energy X-rays (8 keV) due to their greater photoabsorption in water, thus leading the authors to conclude that higher energy (≈36 keV) should be used for future small-angle X-ray scattering (SAXS) experiments on photoswitchable systems. However, this may not always be achievable
  • . With comparison to the rate of Z–E isomerisation on addition of acid to the PS systems, we show that factors beyond the production of protons (H+) upon X-ray radiolysis of water may have an effect to produce the large, rapid structural changes observed using SAXS. To conclude, we create a set of
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Published 14 Aug 2024

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

  • Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

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  • prepared prior to the electrolysis through the condensation of 2-hydrazinopyridine 13 and various aromatic, aliphatic and α,β-unsaturated aldehydes 14. The electrooxidative transformation was performed under constant current at 7 mA in a mixture of acetonitrile and water under heating. From a mechanistic
  • the presence of iodide anion as electromediator. An important challenge is to avoid the competitive formation of the corresponding methoxy(phenylazo)alkane [46][47] or carbonyl compound [48] upon SET anodic oxidation of the hydrazone and subsequent reaction with methanol or water, respectively. In
  • thiocyanation of ketene dithioacetals, Wang and Yang et al. mentioned one example of thiocyanation of benzaldehyde-derived hydrazone 120 using potassium thiocyanate as a source of thiocyanate radical. The electrolysis was conducted in the presence of two equivalents of water in acetonitrile with lithium
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Published 14 Aug 2024

Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

  • Marwa Elsbaey,
  • Naoya Oku,
  • Mohamed S. A. Abdel-Mottaleb and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

Graphical Abstract
  • monitored by TLC. The solution was diluted with water and extracted with EtOAc three times. The organic layer was washed with brine and evaporated to dryness to afford bismethylated derivative of 1 (1a, 1.9 mg, 88% yield). DFT methodology Prior to the calculations of the molecular properties of compounds 2
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Published 13 Aug 2024

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

  • Pengcheng Lu,
  • Luis Juarez,
  • Paul A. Wiget,
  • Weihe Zhang,
  • Krishnan Raman and
  • Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

Graphical Abstract
  • cesium carbonate (766 mg, 2.352 mmol) followed by the necessary tosylate (1.5 equiv). The resulting mixture was stirred for 2 hours at 90 °C. The mixture was poured into EtOAc (500 mL) and washed with water (100 mL) and brine. The organic layer was dried and concentrated, the obtained residue was
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Published 09 Aug 2024

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

  • Vitor A. S. Almodovar and
  • Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

Graphical Abstract
  • and then it was diluted with CH2Cl2 and water. The organic layer was separated and washed with water and brine. The product was isolated by column chromatography on silica gel using CH2Cl2 as the eluent. Yield: 61%; mp: 278–280 °C; 1H NMR (300 MHz, CDCl3) δ (ppm) 7.62–7.66 (m, 4H), 7.47–7.52 (m, 4H
  • and water. The organic layer was then separated and washed with brine and water. The products were isolated by preparative TLC using CH2Cl2/hexane mixtures as the eluent. Compound 3a. Yield: 51%; mp 274–276 °C; 1H NMR (CDCl3, 300 MHz) δ (ppm) 8.43 (AA’XX’, J = 6 Hz, 4H), 7.68 (AA’BB’, J = 8.7 Hz, 4H
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Published 08 Aug 2024

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

  • Ze-Nan Hu,
  • Yan-Hui Wang,
  • Jia-Bing Wu,
  • Ze Chen,
  • Dou Hong and
  • Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

Graphical Abstract
  • zwitterionic water-soluble hypervalent iodine reagent (phenyliodonio)sulfamate (PISA). In water, PISA is strongly acidic, and the pH value can reach 2.05 in a saturated aqueous solution. With PISA, various indoles have been synthesized via C–H amination of 2-alkenylanilines involving an aryl migration
  • product in the reaction, with a yield of 86% in 20 minutes (Table 1, entry 1). Encouraged by this result, we added additives to the reaction with the aim of further increasing the chemical yield of 2a. When 1.5 equivalents of water were added to the reaction, the yield of 2a dropped to 79% (Table 1, entry
  • migration and reductive elimination, along with the release of iodobenzene and sulfamic acid. Cyclization of protonated G takes place to afford the intermediate H. Finally, release of water and β-proton elimination produces the rearranged product 3a (Scheme 8). Conclusion In summary, we reported the
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Published 07 Aug 2024

Electrochemical radical cation aza-Wacker cyclizations

  • Sota Adachi and
  • Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

Graphical Abstract
  • with stirring. The solution was diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Yields were determined by 1H NMR analysis using benzaldehyde as an internal standard (Table 1). Silica gel column
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Published 05 Aug 2024

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

  • Ivan Lyutin,
  • Vasilisa Krivovicheva,
  • Grigory Kantin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

Graphical Abstract
  • -methoxyethylamine. Attempts to obtain directly 2-oxoazetidine carboxylic acid (or its decarboxylation product) or its trifluoroethyl ester by running the synthesis with water or trifluoroethanol were also unsuccessful. Acylation of the π-excessive double bonds of N-alkylindole and dihydropyran by the in situ
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Published 05 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Graphical Abstract
  • catalyst was tested only with 5-aminopyrazole 4, and no comparison with a “classic” GBB reaction can be made, the authors compared HEDP with other catalysts on the same substrates, demonstrating that HEDP in MeOH/water was superior for yields, mildness, and less hazardous conditions (Scheme 3). Longo et al
  • . 1.3 Compartmented and enzyme-mediated reactions Compartmentation of reaction media has already found many applications in chemistry. Amphiphilic molecules can associate in water to nanometer-sized micelles, above a certain critical concentration. Such micelles are characterized by a lipophilic core
  • and a hydrophilic corona and can serve as heterogeneous systems for solubilizing hydrophobic chemicals in water. By concentrating reactants in nanometer-sized vessels, their reactivity is altered, and reaction rates are often accelerated. As a result, mild reaction conditions can be achieved
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Published 01 Aug 2024

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

  • Ivana Weisheitelová,
  • Radek Cibulka,
  • Marek Sikorski and
  • Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

Graphical Abstract
  • , water), which has become a common method for the synthesis of these derivatives [3][22][25][30][31][32][33]. In our previous studies [14][15][16][17][18][19] we have shown that the 5-aryl and 7,8-substitutients of the pyrimido[4,5-b]quinoline core have a significant effect on the photocatalytic activity
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Published 31 Jul 2024

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

  • Moisés Alejandro Alejo Hernandez,
  • Katia Pamela Villavicencio Sánchez,
  • Rosendo Sánchez Morales,
  • Karla Georgina Hernández-Magro Gil,
  • David Silverio Moreno-Gutiérrez,
  • Eddie Guillermo Sanchez-Rueda,
  • Yanet Teresa-Cruz,
  • Brian Choi,
  • Armando Hernández Garcia,
  • Alba Romero-Rodríguez,
  • Oscar Juárez,
  • Siseth Martínez-Caballero,
  • Mario Figueroa and
  • Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

Graphical Abstract
  • 0.1% w/v poly-ʟ-lysin solution in water (Sigma-Aldrich) and immediately deposited onto freshly cleaved mica to be incubated for 10 min at room temperature to allow adsorption. The surface was then rinsed using 600 µL of ultrapure 0.2 µm filtered water and slowly dried using compressed air. Imaging was
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Published 30 Jul 2024

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

  • Samuel M. G. Dearman,
  • Xiang Li,
  • Yang Li,
  • Kuldip Singh and
  • Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

Graphical Abstract
  • rate of decomposition was reduced significantly (green line in Figure 3). The hydrolysis of the four hypervalent iodine(V) fluorides was also investigated in acetonitrile-d3 by adding 5 equivalents of water. All four compounds decomposed to their corresponding iodosyl compounds and the order of
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Published 29 Jul 2024

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

  • Alexander V. Tsygankov,
  • Vladyslav O. Vereshchak,
  • Tetiana O. Savluk,
  • Serhiy M. Desenko,
  • Valeriia V. Ananieva,
  • Oleksandr V. Buravov,
  • Yana I. Sakhno,
  • Svitlana V. Shishkina and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

Graphical Abstract
  • chlorine atom in the chlorovinyl fragment to the hydroxy group, probably under the influence of water (Figure 4). It is worth noting that the synthesis of Ugi bisamides 5–8 (Table 1) yielded compounds 10 and ketobisamide 12 in some cases. For example, in the Ugi reaction involving benzyl isocyanide (4b
  • moiety under the influence of water. The appearance of HCl in these cases was identified by the specific odor and detected by pH measurements. It is likely that this catalytic amount of HCl is enough for the conversion and formation of the amides 10. To confirm the influence of HCl and its necessity to
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Published 26 Jul 2024

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

  • Hiwot M. Tiruye,
  • Solon Economopoulos and
  • Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

Graphical Abstract
  • control of the current [32][33][34]. Early studies on the electrochemical oxidation of phenols revealed that the oxidation passes through a phenoxonium ion and forms acetals in methanol but quinones in the presence of water [35][36][37]. However, the reaction is sometimes accompanied by the formation of
  • shown), where methanol further served as nucleophile. Some THF was needed to improve the solubility of some of the substrates. Acidic conditions (Table 1, entry 5) or methanol/water (Table 1, entry 6) gave a complex mixture with overoxidized products. Although the desired oxidation is a 4-electon
  • flowrate of 100 µL/min. The current was increased from 1 mA to 13 mA to increase the electron equivalents from 1 F/mol to 8 F/mol at a potential of 1.7–3.0 V. The crudes, after evaporation of the solvents, were further hydrolysed with a mixture of HCl, acetic acid, and water to release the quinones before
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Published 24 Jul 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • spirosteroids was underscored by the synthesis of spironolactone [3] (Figure 1), which plays a pivotal role in edema treatment. Aldosterone, implicated in water and salt retention in conditions such as congestive heart failure, hypertension, nephrosis, liver cirrhosis, and toxemia of pregnancy, prompted the
  • water–NaOAc mixture. Spiro heterocycle 99 was obtained in 52% overall yield as a single product (Scheme 29). The reaction mechanism was elucidated based on the hard and soft acid and base theory. Spiro-1,3,4-thiadiazoline steroids In 2006, Mazoir et al. [56] reported the synthesis of 4α,14α-dimethyl-5α
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Published 24 Jul 2024

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

  • Ryo Tanifuji and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

Graphical Abstract
  • approach, they used a chiral boron catalyst as a Lewis acid and achieved at best an endo/exo selectivity of 1.9:1 in a similar DA reaction. The use of Diels–Alderase in their recent work significantly improved the endo/exo selectivity under mild conditions in water, thereby highlighting the strengths of
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Published 23 Jul 2024

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

  • Weimao Zhong and
  • Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

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  • diverse marine holobionts such as sponges [3][4], sediments [5], algae [6], and corals [7] using media that mimic the native salt water habitat. Strains of this genus are detected together with Pseudovibrio and Ruegeria strains that grow in identical culture conditions, and hence obtaining axenic
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Published 17 Jul 2024

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

  • Fátima C. Teixeira,
  • António P. S. Teixeira and
  • C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

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  • . Romão Ramalho, 59, 7000-671 Évora, Portugal 10.3762/bjoc.20.145 Abstract A new paradigm for energy is underway demanding decarbonized energy systems. Some of them rely on emerging electrochemical devices, crucial in hydrogen technologies, including fuel cells, CO2 and water electrolysers, whose
  • applications and performances depend on key components such as their separators/ion-exchange membranes. The most studied and already commercialized Nafion membrane shows great chemical stability, but its water content limits its high proton conduction to a limited range of operating temperatures. Here, we
  • exchange membrane devices [5][6], such as proton exchange membrane fuel cells (PEMFCs) [3][7][8][9], due to their high-power density and high power-to-weight ratio, and CO2 electrolysers, which can reduce the polluting gas CO2 and produce syngas from the co-electrolysis of CO2 and water [10][11], or water
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Published 17 Jul 2024
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