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Search for "water" in Full Text gives 2187 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Copper-catalyzed yne-allylic substitutions: concept and recent developments

  • Shuang Yang and
  • Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

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  • , 6a–w). Interestingly, both Cu(I) and Cu(II) can promote the reaction and the reaction is not sensitive to water (Scheme 7, 6g). The intramolecular decarboxylative yne-allylic substitution can also be achieved (Scheme 8, 6a–u). O-Nucleophiles and C-nucleophiles are all suitable reactants, yielding
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Published 31 Oct 2024

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

  • Francesco Gambuti,
  • Jacopo Pizzorno,
  • Chiara Lambruschini,
  • Renata Riva and
  • Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

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  • optimized reaction conditions, we observed good conversion of the starting material, but the desired compound was isolated in very poor yield, as the α-aminoamide 4a resulted the main product (Table 1, entry 1). We were surprised about that, as, even if water is present as co-solvent in the reaction mixture
  • , we have never noted the formation of the α-aminoamide in our previous work. Repeating the reaction in the absence of water suppressed the 4a formation but with a concomitant drop of the conversion, resulting again in a poor yield of 2a (Table 1, entry 2). Thus, we demonstrated that GO was able to
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Published 29 Oct 2024

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

  • Ruben Manuel Figueira de Abreu,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

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  • stirred for 4 hours under argon atmosphere at 100 °C. The reaction was monitored by TLC until completion. The reaction was neutralised with a saturated NaHCO3 solution and diluted with water (40 mL). The phases were separated, and the aqueous layer was extracted with dichloromethane (3 × 30 mL). The
  • (PPh3)4 (10 mol %), NaOH (3 equiv), 1,4-dioxane/water 5:1, 100 °C, 1 h; iv) p-TsOH (20 equiv), toluene, 100 °C, 4 h. Synthesis and isolated yields of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 4a–i. Reaction conditions: 3 (1 equiv), boronic acid (1.2 equiv), Pd(PPh3)4 (5 mol %), NaOH (3 equiv), 1,4
  • -dioxane/water 5:1, 100 °C, 1 h. Scope and isolated yields of the synthesis of 5. Reaction conditions: 4 (1 equiv), p-TsOH·H2O (20 equiv), toluene, 100 °C, 4 h. Proposed reaction mechanism of the cyclisation with N,N-dimethylanilino functional groups. Optimization of the synthesis of 5a. Photophysical data
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Published 28 Oct 2024

Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

  • Yukiko Karuo,
  • Keita Hirata,
  • Atsushi Tarui,
  • Kazuyuki Sato,
  • Kentaro Kawai and
  • Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

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  • parent compounds. Furthermore, fluoroalkenes can be utilized as feedstock for fluoropolymers. Teflon, which is a well-known fluoropolymer with excellent water-repellent and oleophobic properties, is synthesized by polymerizing a monomer called tetrafluoroethylene. As a consequence, convenient and diverse
  • mol %), cesium carbonate (1.5 equiv), palladium bis(trifluoroacetate) (5 mol %) in THF (2.0 mL) was added the respective boronic acid derivative 4 (2.0 equiv). The reaction solution was refluxed for 3.5 h. The reaction mixture was quenched by the addition of water (40 mL) at 0 °C and extracted with
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Published 24 Oct 2024

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

  • Bhaskar B. Dhotare,
  • Seema V. Kanojia,
  • Chahna K. Sakhiya,
  • Amey Wadawale and
  • Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

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  • environmental hazards, and this can only be circumvented using a transition-metal-free synthesis protocol. Although eco-friendly methods for the synthesis of 2-hydroxybenzophenones have been reported via a cycloaromatization of α-alkenoyl ketene dithioacetals and nitroethane in water [15], an alternate and more
  • cold 10% aqueous NaHCO3 solution was added. The reaction mixture was diluted with EtOAc and filtered through a Celite bed. The filtrate was extracted with ethyl acetate (3 × 40 mL), the organic extract was washed with water and brine, and dried with Na2SO4. The organic extract was concentrated under
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Published 21 Oct 2024

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

  • Jonas Holste,
  • Paul Weldon,
  • Donald Boyer and
  • Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

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  • for 18 h. After cooling down to room temperature, water, and diethyl ether were added. The phases were separated and the aqueous phase was extracted three times with diethyl ether. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated for GC–MS analysis [44
  • analysis [8]. Silver nitrate column chromatography: Silver nitrate column chromatography was carried out as described [45]. An aq solution of silver nitrate (5.5 g) in H2O (30 mL) was added to silica gel (50 g). Water was added to barely cover the silica gel. The silica was stirred with a glass rod and
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Published 18 Oct 2024

Deciphering the mechanism of γ-cyclodextrin’s hydrophobic cavity hydration: an integrated experimental and theoretical study

  • Stiliyana Pereva,
  • Stefan Dobrev,
  • Tsveta Sarafska,
  • Valya Nikolova,
  • Silvia Angelova,
  • Tony Spassov and
  • Todor Dudev

Beilstein J. Org. Chem. 2024, 20, 2635–2643, doi:10.3762/bjoc.20.221

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  • substances. Host CDs are highly accommodative to water molecules as well and usually contain water in the native state. There is still an ongoing discussion on both the total number of water molecules and their preferred binding position inside the cavities of the CDs. To understand the hydration/dehydration
  • light on the mechanism of the γ-CD hydration and to address some unanswered questions: (i) what are the preferable locations for water molecules in the macrocyclic cavity (“hot spots”); (ii) what are the major factors contributing to the stability of the water cluster in the CD interior; (iii) what type
  • of interactions (i.e., waterwater and/or water–CD walls) contribute to the stability of the water assemble; (iv) how does the mechanism of the γ-CD hydration compare with those of its α-CD and β-CD counterparts. Keywords: cyclodextrin; DFT calculation; DSC/TG; hydration; thermodynamic
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Published 17 Oct 2024

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

  • Connor R. M. MacDonald and
  • Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

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  • , the bulk gel (which may not be the same as the surface) is inaccessible and cannot be characterised. AFM has the advantage of allowing for the measurement of hydrated samples, and therefore does not suffer from drying artefacts. Since hydrogels are mainly made of water and low concentration hydrogels
  • the range of hierarchical assemblies [32]. Another significant concern posed by blotting is the brief introduction of an air–water interface which can lead to preferential organisation of particles, as well as unpredictable changes in local concentration on the TEM grid [41]. To overcome such
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Published 16 Oct 2024

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

  • Alfiya R. Gimadieva,
  • Yuliya Z. Khazimullina,
  • Aigiza A. Gilimkhanova and
  • Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

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  • distilled water, 6-methyluracil (99%, Chemical Line LLC, Russia), pyridine (analytically pure grade, Reakhim LLC, Russia), (NH4)2S2O8 (analytically pure grade, Panreac), NaOH (analytically pure grade, Reakhim LLC, Russia), H2SO4 (reagent grade, LLC Sigma Tech, Russia), dimethyl sulfate (99%, Chemical Line
  • by РсМ. As described in [13] to a three-necked flask of 100 mL capacity, equipped with a mechanical stirrer, a thermometer, and a reflux condenser, containing 10 mL of distilled water, was added 0.023 mol of the corresponding uracil 1 or 4, followed by the addition of 11 mL of a previously prepared
  • mixture to room temperature, concentrated H2SO4 was slowly added until pH 6–7 according to litmus paper and left standing for 12 h. The precipitated white crystals were filtered off, washed with water, and dried in air. Compound 2 yields are given in [13] and compound 5 yields are given in Table 1. b
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Published 16 Oct 2024

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

  • Battini Veeraiah,
  • Kishore Ramineni,
  • Dabbugoddu Brahmaiah,
  • Nangunoori Sampath Kumar,
  • Hélène Solhi,
  • Rémy Le Guevel,
  • Chada Raji Reddy,
  • Frédéric Justaud and
  • René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

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  • stirred at −78 °C for 2 h, and then dry DMF (3.3 mL, 0.041 mol) was added. After stirring for 2 h at −78 °C, the mixture was quenched with water and the crude product was extracted with ethyl acetate (30 mL × 3). The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated under
  • ]quinazolin-2-amine (3): To a stirred solution of guanidinium carbonate (2.0 g, 0.011 mol) in DMA (15 mL) was added compound 2 (1.5 g, 0.008 mol). Then the reaction mixture was heated to stir at 150 °C for 16 h. After completion of the reaction (TLC), the mixture was poured into ice water, a solid was formed
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Published 14 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

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  • further emphasized its utility. Mechanistic studies have demonstrated that the key to this selective chemical conversion lies in the dual oxidation process at the anode. The authors suggest that anodic oxidation of the sulfide generates a sulfur radical cation intermediate, which reacts with water at the
  • the hydrosilane to generate a silyl radical. This silyl radical is then oxidized anodically to produce a silyl cation. The silyl cation subsequently abstracts a proton from water (H2O), forming the desired silanol product (Scheme 28). While many methods combining metal catalysis and electrochemistry
  • − is protonated to produce DDQH2. The anodic oxidation of DDQH2 regenerates DDQ, which re-enters the catalytic cycle (Scheme 29). Furthermore, Qiu and coworkers disclosed a metal-free electrochemical dihydroxylation of unactivated alkenes using water as the hydroxy source under air conditions [40
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Published 09 Oct 2024

Visible-light-mediated flow protocol for Achmatowicz rearrangement

  • Joachyutharayalu Oja,
  • Sanjeev Kumar and
  • Srihari Pabbaraja

Beilstein J. Org. Chem. 2024, 20, 2493–2499, doi:10.3762/bjoc.20.213

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  • obtained when EtOAc (flow rate set at 2.5 mL/min), water (flow rate set at 4.5 mL/min) were taken with the extraction time of 0.25 min and separation time of 0.11 min (see details in Supporting Information File 1, Table S2, entry 5). To verify the steadiness of the newly constructed integrated photo-flow
  • OH). The Achmatowicz product is formed by addition of water to oxocarbenium intermediate A followed by elimination of L. Conclusion In conclusion, an integrated continuous PFR platform for photocatalytic functionalization of furfuryl alcohols to dihydropyranones through an Achmatowicz rearrangement
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Published 08 Oct 2024

Phenylseleno trifluoromethoxylation of alkenes

  • Clément Delobel,
  • Armen Panossian,
  • Gilles Hanquet,
  • Frédéric R. Leroux,
  • Fabien Toulgoat and
  • Thierry Billard

Beilstein J. Org. Chem. 2024, 20, 2434–2441, doi:10.3762/bjoc.20.207

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  • separatory funnel and 10 mL of water are added. The aqueous layer is extracted three times with 10 mL of diethyl ether. The organic layers are combined and washed with 10 mL of water. The organic layer is dried with MgSO4, filtered, and concentrated under vacuum. Compounds 2 are obtained after purification
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Published 26 Sep 2024

Homogeneous continuous flow nitration of O-methylisouronium sulfate and its optimization by kinetic modeling

  • Jiapeng Guo,
  • Weike Su and
  • An Su

Beilstein J. Org. Chem. 2024, 20, 2408–2420, doi:10.3762/bjoc.20.205

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  • , 98.0%) was purchased from Sinopharm Chemical Reagent Co., Ltd.; pure water from AR, Hangzhou Wahaha Group Co., Ltd.; all reagents were used without further purification. Sulfuric acid solutions of different mass fractions were prepared with pure water and 98% concentrated sulfuric acid in an ice bath
  • reaction coil. All preheat tubes, mixers, and reaction coils were immersed in the same water bath to maintain a constant temperature. Finally, after controlling the residence time, the reaction was terminated by pumping excess pure ice water through a high-pressure PTFE pump (Pump C, JJRZ-10004F, Hangzhou
  • thermometer connected to the outlet. Sample analysis When the continuous flow system was operated at steady state (after 2–3 times the residence time), the reaction solution was quenched and diluted by a large amount of ice water at the outlet of the reaction system. The quenched and diluted reaction solution
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Published 24 Sep 2024

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

  • Andreas Wiest and
  • Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

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  • conjugates may be carried out using desthiobiotin (DTB) as affinity tag instead of biotin [103][104]. The DTB-tag allows to elute probe–peptide–DTB conjugates from streptavidin beads using a mixture of water, organic solvent – typically acetonitrile (ACN) – and an acid such as formic acid. The desthiobiotin
  • tag in cell lysate, the proteins are loaded onto the carboxylate magnetic beads and aggregated with the beads by addition of an organic solvent, for example ethanol or acetonitrile. The subsequent washes of the carboxylate magnetic beads with proteins by an organic solvent–water mixture or organic
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Published 12 Sep 2024

Stereoselective mechanochemical synthesis of thiomalonate Michael adducts via iminium catalysis by chiral primary amines

  • Michał Błauciak,
  • Dominika Andrzejczyk,
  • Błażej Dziuk and
  • Rafał Kowalczyk

Beilstein J. Org. Chem. 2024, 20, 2313–2322, doi:10.3762/bjoc.20.198

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  • by extended reaction times, sometimes up to 168 hours. An intriguing example involves the use of a bifunctional primary amine-sulfonamide catalyst, which activates benzylideneacetone towards dibenzyl malonate, with the presence of water accelerating the reaction [25]. An alternative approach, where
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Published 12 Sep 2024

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

  • Stefan P. Schmid,
  • Leon Schlosser,
  • Frank Glorius and
  • Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

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Published 10 Sep 2024

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

  • Kevin Schofield,
  • Shayna Maddern,
  • Yueteng Zhang,
  • Grace E. Mastin,
  • Rachel Knight,
  • Wei Wang,
  • James Galligan and
  • Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

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  • preparation of 4d, a deuterated isocyanide was solely employed and for 4a,b and 4e,f, water was used as solvent. For the latter, product precipitates from the aqueous solution which deters undesirable side-reactions whilst also aiding rate of the reaction. The fifth MCR employed herein is the ubiquitous
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Published 06 Sep 2024

Synthesis and reactivity of the di(9-anthryl)methyl radical

  • Tomohiko Nishiuchi,
  • Kazuma Takahashi,
  • Yuta Makihara and
  • Takashi Kubo

Beilstein J. Org. Chem. 2024, 20, 2254–2260, doi:10.3762/bjoc.20.193

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  • pathway involving hydrogen abstraction from water yielding 4, and a major pathway involving oxygen addition to the central carbon to afford 1,2-dioxetane (DOT) intermediate. Usually, DOT derivatives are known to readily decompose [38], and this DOT intermediate is also considered to decompose upon C–C and
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Published 05 Sep 2024

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

  • Tabea Bartsch,
  • Stephan Lütz and
  • Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

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  • are not well described yet. To date, standard conditions have mainly been used for CFPS, with little systematic testing of whether conditions closer to intracellular conditions in terms of viscosity, macromolecules, inorganic ions, osmolarity, or water content are advantageous. Also, very few non
  • -physiological conditions further extend the parameter space in which CFPS can be performed. This extension would be highly desirable for a coupled CFPS and enzyme assay, where, e.g., an organic solvent is used to solubilize poorly water soluble substrates for the enzyme. In this study, we therefore aim to fill
  • some of the gaps in the consideration of the general physical properties and potential effects on the performance of Escherichia coli-based CFPS. We use technical additives, such as water-soluble macromolecular polymers and salts, which are commonly used as deep eutectic solvents (DES) and extend the
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Published 04 Sep 2024

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

  • Haifeng Yu,
  • Wanting Zhang,
  • Xuejing Cui,
  • Zida Liu,
  • Xifu Zhang and
  • Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

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  • Haifeng Yu Wanting Zhang Xuejing Cui Zida Liu Xifu Zhang Xiaobo Zhao College of Chemistry, Baicheng Normal University, Baicheng, Jilin 137000, China 10.3762/bjoc.20.190 Abstract An eco-friendly selective hydrolysis of chain α-oxo ketene N,S-acetals in water for the switchable synthesis of β-keto
  • thioesters and β-keto amides is reported. In refluxing water, the hydrolysis reactions of α-oxo ketene N,S-acetals in the presence of 1.0 equiv of dodecylbenzenesulfonic acid effectively afforded β-keto thioesters in excellent yield, while β-keto amides were successfully obtained in excellent yield when the
  • synthetic method for the preparation of β-keto thioesters and β-keto amides remains imperative. Organic reactions in water are an important and exciting research topic of green chemistry because water as a solvent exhibits fascinating features, such as low cost, good environmental compatibility, nontoxicity
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Published 03 Sep 2024

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

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  • 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
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