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Search for "ethanol" in Full Text gives 750 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents

  • Julius Krenzer and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97

Graphical Abstract
  • -N-benzylbenzothiazolium salts in 1,4-dioxane at room temperature in short reaction time in 20–99% yield. This protocol represents a considerable improvement over the standard synthesis in 1,4-dioxane/ethanol mixtures at elevated temperatures. Keywords: aroyl chlorides; aroyl-S,N-ketene acetals
  • of an amine base in a binary 1,4-dioxane/ethanol mixture. Ethanol was used as a cosolvent to ensure solubility of the polar intermediate according to the mechanistic rationale (Scheme 2) [5][6]. Although, a broad scope of diversely substituted (hetero)aroyl-S,N-ketene acetals 8 was obtained (111
  • presumed byproducts in the addition–elimination sequence in the presence of an excess of ethanol as a cosolvent are the ethyl ester formed by Einhorn acylation [7] of the acid chloride under the standard conditions and deep colored polar byproducts (according to TLC detection) that arise from self
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Published 20 Jun 2025

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

Graphical Abstract
  • % yield over three steps. This compound was isolated in its pure form as a white solid after recrystallization from ethanol, confirmed by HPLC and NMR. In parallel, the primary alcohol group of ent-38 was protected as a TBDMS ether, and the acetate group was converted to a tosyl ester by hydrolyzing the
  • reduced with LiAlH4 to remove the OTs group, and after silyl group removal, diol 32b was obtained in 92% yield. Protection of the primary alcohol as a tosyl ester and the secondary as a TBDMS ether afforded intermediate 32c (72%). This intermediate was then treated with sodium thiophenol in ethanol
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Published 12 Jun 2025

Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes

  • Linqiang Wang and
  • Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86

Graphical Abstract
  • , dried over sodium sulfate, and freshly distilled prior to use. All solid aldehydes were used after recrystallization from petroleum ether (PE, 60–90 °C fraction) or a mixture of ethanol and water. All dialkyl 3-aryl-1-sulfonylaziridine-2,2-dicarboxylates 1 were synthesized by previously reported
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Published 28 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

Graphical Abstract
  • alkyldiamines proceeded with solvent-independent regioselectivity, exclusively furnished [2 + 2] macrocyclic adducts. Strikingly, when 37 was combined with 2,2’-oxybis(ethylamine) (38), the reaction pathway exhibited pronounced solvent dependency. Reactions in methanol, ethanol, or chloroform selectively
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Published 07 May 2025

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

  • Nguyen Tran Nguyen,
  • Vo Viet Dai,
  • Luc Van Meervelt,
  • Do Thi Thao and
  • Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

Graphical Abstract
  • -pyrroline-2-ones 1a–e and 4-methoxybenzylamine (2) in absolute ethanol yielded 4-[1-(4-methoxybenzyl)amino]ethylidene-1,5-disubstituted pyrrolidine-2,3-diones 3a–e (Scheme 1) [19][20][21]. In addition to nuclear magnetic resonance spectroscopy (1D, 2D NMR), the structure of 3a has also been proven via
  • pyrrolidine-2,3-diones 3b–e are not expected to affect the scope of the reaction (Scheme 2, Table 1). When the reaction between 3a (1 equiv) and methylamine (4) (4 equiv, 40% in water) was carried out in absolute ethanol (0.3 mL) at reflux, 4-(1-methylamino)ethylidene-1,5-diphenylpyrrolidine-2,3-dione (5a
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Published 24 Apr 2025

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

  • Raphael Bereiter and
  • Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

Graphical Abstract
  • nucleophilic aromatic substitution of 4-fluorobenzaldehyde with 2-(methylamino)ethanol, 3-methylamino-1-propanol or 2-[2-(methylamino)ethoxy]ethan-1-ol in the presence of potassium carbonate to afford benzaldehyde derivatives 1, 2, and 3 in excellent yields. Next, the piperidine-induced condensation with 4
  • Na2SO4 and concentrated to dryness. Finally, the crude compound was purified via silica gel chromatography using 50–70% ethyl acetate in cyclohexane as gradient. General procedure B. The product obtained in general procedure A was dissolved in ethanol mixed with 4-cyanophenylacetonitrile and 8 drops of
  • piperidine and stirred at 100 °C for 20 hours. A strongly yellow-colored solution was obtained and cooled on ice, whereby a precipitate was formed and filtered off. The filter cake was washed with ice-cold ethanol and dried under high vacuum. General procedure C. In a manner similar to [11], the product
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Published 04 Apr 2025

Origami with small molecules: exploiting the C–F bond as a conformational tool

  • Patrick Ryan,
  • Ramsha Iftikhar and
  • Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

Graphical Abstract
  • progress from ethers (section 2) to a closely related class of molecules, namely, the alcohols. The focus here in section 3 will be mostly on simple examples; more complex poly-ol examples will be discussed in section 4 (sugars). Taking the example of a simple alcohol such as ethanol, consider what happens
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Published 02 Apr 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • carbon atom, due to the readiness for losing a water molecule. Formaldehyde is commonly used in its polymeric form (paraformaldehyde) or in a 37% aqueous solution (formalin). The exceptional solubility of formaldehyde in water or biobased solvents, such as ethanol and glycerol, enhances the feasibility
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Published 13 Mar 2025

Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles

  • Constantine V. Milyutin,
  • Andrey N. Komogortsev and
  • Boris V. Lichitsky

Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44

Graphical Abstract
  • under various conditions. Initially, we performed the studied process with equivalent amounts of starting materials in ethanol at reflux for 1 h. As a result, no products of condensation or recyclization have been obtained. At the same time, stable salt 3a was isolated in 95% yield (Scheme 2a). Besides
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Published 13 Mar 2025

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

  • James Guevara-Pulido,
  • Fernando González-Pérez,
  • José M. Andrés and
  • Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

Graphical Abstract
  • of 18 with Raney nickel in ethanol at room temperature gave a 3:1 mixture of anti/syn-19. The absolute configuration of anti-19 is (2R,3S), indicating that in the resolution process, the major enantiomer corresponds to the anti-(3S,4R)-5-oxo-3,4,5-triphenylpentanal. Having established that the major
  • in ethanol (5 mL), and Raney-Ni was added and stirred at room temperature for 12 h. Then, the mixture was filtered, the solid was washed four times with ethanol, and the resulting solution was concentrated under reduced pressure. The residue was purified by a silica gel chromatographic column (eluent
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Published 03 Mar 2025

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

  • Ayesha Saeed,
  • Shahana Ehsan,
  • Muhammad Zia-ur-Rehman,
  • Erin M. Marshall,
  • Sandra Loesgen,
  • Abdus Saleem,
  • Simone Giovannuzzi and
  • Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

Graphical Abstract
  • of pyrazolo-1,2-benzothiazine derivative 5 A solution of compound 4 (269 mg, 1 mmol) in ethanol (10 mL) was refluxed with excess of hydrazine monohydrate for 24 hours. After the completion of reaction, unreacted hydrazine was removed under vacuum. Cold acidified water was poured into the residue
  • . Yellow-colored precipitates of product 5 were formed which were separated via filtration followed by washing with excess of water. After drying, recrystallization was done with ethanol. Mp 265–266 °C; yield: 221 mg (88%). Synthesis of pyrazolo-1,2-benzothiazine-N-aryl/benzyl/cyclohexylacetamides 7a–h
  • diluted with cold water and acidified with 5% cold HCl. The solution was allowed to stand for 15 minutes to complete precipitation. Precipitates were collected via filtration and washed with excess distilled water. The dried product was then recrystallized from absolute ethanol. Synthesis of pyrazolo-1,2
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Published 12 Feb 2025

Red light excitation: illuminating photocatalysis in a new spectrum

  • Lucas Fortier,
  • Corentin Lefebvre and
  • Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

Graphical Abstract
  • alcohols 32. Notably, this protocol is both energy-efficient and operationally simple, with the reaction being carried out under air in ethanol, a low-toxicity solvent. Moreover, the scalability of the reaction was demonstrated with larger-scale experiments (up to 5 mmol), achieving excellent yields and
  • minimal waste. The authors further showcased the robustness of the method by utilizing common kitchen equipment, mixing spinach extract with Baijiu (a traditional Chinese drink with a high level of ethanol) and stirring the reaction under sunlight, achieving yields as high as 60%. This demonstration
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Published 07 Feb 2025

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

  • Dmitry E. Shybanov,
  • Maxim E. Kukushkin,
  • Eugene V. Babaev,
  • Nikolai V. Zyk and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

Graphical Abstract
  • alcohol 2. Its 1H NMR spectrum contained a triplet with a coupling constant of 5.1 Hz at 5.52 ppm and a doublet at 4.30 ppm. In methanol, ethanol and petroleum ether, with an increasing reaction time, a significant amount of product 3 was observed in the 1H NMR spectra of the mixtures, as identified by
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Published 04 Feb 2025

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

Graphical Abstract
  • -workers in 2003 (Scheme 13) [28]. Working in acetonitrile at room temperature, very high yields were obtained with recycling of the catalyst with negligible loss of activity. The reaction is successful also by operating it in ethanol as a solvent under microwave irradiation [29]. More recently, the
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Published 14 Jan 2025

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

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Published 09 Jan 2025

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

  • Yang Chen,
  • Jiao He,
  • Hang Lin,
  • Hai-Feng Wang,
  • Ping Hu,
  • Bi-Qin Wang,
  • Ke-Qing Zhao and
  • Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

Graphical Abstract
  • analysis (Figures S1–S32, Supporting Information File 1), and all the results agree with the proposed molecular structures. Single-crystal structure of F Suitable single crystals of compound F for X-ray analysis were obtained by slow evaporation of an ethyl acetate/ethanol solution (Figure 2, and
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Published 16 Dec 2024

Synthesis of 2H-azirine-2,2-dicarboxylic acids and their derivatives

  • Anastasiya V. Agafonova,
  • Mikhail S. Novikov and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2024, 20, 3191–3197, doi:10.3762/bjoc.20.264

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  • single-crystal X-ray diffraction analysis. The reaction of azetidine with diacyl chloride 2a gave a complex mixture of products, and O-methyl hydroxylamine did not react. Diacyl chloride 2a reacts with methanol and ethanol to give diesters 11a,b (Scheme 5). An experiment with isoxazole 1a and methanol on
  • -2,2-dicarboxamides were prepared using primary and secondary amines in 53–84% yield, and the reaction is scalable. Methyl and ethyl esters of 3-phenyl-2H-azirine-2,2-dicarboxylic acid were prepared in 76–99% yield from 3-phenyl-2H-azirine-2,2-dicarbonyl dichloride and methanol or ethanol, but the
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Published 05 Dec 2024

Extension of the π-system of monoaryl-substituted norbornadienes with acetylene bridges: influence on the photochemical conversion and storage of light energy

  • Robin Schulte,
  • Dustin Schade,
  • Thomas Paululat,
  • Till J. B. Zähringer,
  • Christoph Kerzig and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 3061–3068, doi:10.3762/bjoc.20.254

Graphical Abstract
  • acetylenes at ca. 85 ppm and 95 ppm were observed. The norbornadienes 1h–l,n exhibit very good solubility in organic solvents, like ethyl acetate, chloroform, or benzene, whereas they have poor solubility in cyclohexane, acetonitrile, or ethanol. In polar protic solvents, like methanol or water, they are
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Published 21 Nov 2024

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

  • Ritu Mamgain,
  • Kokila Sakthivel and
  • Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

Graphical Abstract
  • easily recycled just by washing it with ethanol, retaining its catalytic activity for arylation up to three cycles without any compromise. Thus, this procedure could be considered economic as well as environment-friendly. In 2019, Kalek and co-workers reported the regioselective C–H arylation of 2
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Published 13 Nov 2024

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

  • Marzieh Norouzi,
  • Mohammad Taghi Nazeri,
  • Ahmad Shaabani and
  • Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

Graphical Abstract
  • , and DMF at different temperatures (Table 1, entries 3–9). The result obtained from the study of solvents showed that pyrrole-fused dibenzoxazepine 4a was obtained with a yield of 56% in ethanol as solvent at a temperature of 78 °C (Table 1, entry 4). To achieve a higher yield of product 4a, the
  • their suitable fluorophores [49][50][51]. The UV–vis absorption and emission spectra of products 4 and 6 were studied in ethanol at 298 K. The absorption range (λabs) was 400–225 nm, and the emission range (λem) was 560–400 nm. These findings are shown in Figure S3 in Supporting Information File 1. An
  • QS (quinine sulfate) (a); emission for 4a, 6c and QS (b); c = 75 ppm in ethanol and T = 298 K. Methods for the construction of pyrrole-fused heterocycles through I-MCR reactions. The model reaction of dibenzoxazepine, gem-diactivated olefin (2-benzylidenemalononitrile), and cyclohexyl isocyanide
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Published 11 Nov 2024

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

  • Dmitriy Yu. Vandyshev,
  • Daria A. Mangusheva,
  • Khidmet S. Shikhaliev,
  • Kirill A. Scherbakov,
  • Oleg N. Burov,
  • Alexander D. Zagrebaev,
  • Tatiana N. Khmelevskaya,
  • Alexey S. Trenin and
  • Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

Graphical Abstract
  • intramolecular cyclization were observed (Table 1, entries 3 and 4). The best results were obtained when isopropyl alcohol was used, which furnished yields of the final product 4а up to 89% within 1 h (entry 9 in Table 1). In the case of methanol and ethanol, the maximum conversion was also observed during the
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Published 05 Nov 2024

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

  • Hayato Takagi,
  • Çetin Çelik,
  • Ryosuke Fukuda,
  • Qi Guo,
  • Tomohiro Higashino,
  • Hiroshi Imahori,
  • Yoko Yamakoshi and
  • Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

Graphical Abstract
  • Plains, NY, USA) was solubilized in ethanol (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan), and catC60, which was synthesized according to a previous report [20], or C60 (NOF AMERICA Corporation, White Plains, NY, USA) was solubilized in a 1:4 (vol:vol) mixture of DMSO (Nacalai Tesque Inc
  • ., Kyoto, Japan) and toluene (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan). DMPC in ethanol and catC60 or C60 in DMSO/toluene were mixed in molar ratios of 1:0, 1:0.1, 1:1, or 1:10, and the solvent was removed using a rotary evaporator (Rotavapor R-300, BÜCHI Labortechnik AG, Switzerland) at 40
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Published 30 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

Graphical Abstract
  • -absorption studies UV–vis absorbance spectra of the 5-substituted-2-hydroxybenzophenones 4aa–ka were recorded in triplicates at room temperature (298 K) in ethanol at a concentration of 40 µM, in the range of 225–500 nm at 1 nm intervals [11]. The obtained data were corrected using calibration methods with
  • ethanol as a blank. The critical wavelength (λc) and UVA/UVB ratio were calculated using Equation 1 and Equation 2, respectively, as shown below. Determination of SPF (sun protection factor) An ethanolic solution of the compounds 4aa–ka was prepared at a concentration of 200 μg/mL. The UV–vis absorption
  • spectra of samples were measured in the range of 290 to 450 nm, every 5 nm, using ethanol as a blank [11]. The absorption data were obtained in three replicates at each point, and the SPF value was calculated using Equation 3. Where, CF (correction factor) = 10; EE(λ) is the erythemal effect spectrum; I(λ
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Published 21 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

Graphical Abstract
  • H2SO4 was added and the reaction mixture was stirred at the same temperature for 1 h and cooled. The precipitated crystals were filtered off, washed with cold distilled water to pH 6–7 (2 × 5 mL), and recrystallized from ethanol. 5-Hydroxy-6-methyluracil (3). Yield 98%. The spectral characteristics are
  • at 45 °C for 10 h, cooled to room temperature, evaporated at reduced pressure to 1/3 volume, extracted with ethyl acetate (2 × 20 mL) to remove unreacted pyridine, followd by butanol (3 × 50 mL). The butanol fractions were combined and evaporated to dryness. The residue was washed with hot ethanol
  • with ethyl acetate (2 × 20 mL) to remove unreacted pyridine, followed by butanol (3 × 50 mL). The butanol fractions were combined and evaporated to dryness. The residue was washed with hot ethanol, kept for 12 h at 0 °C, the precipitate was decanted, and the filtrate was evaporated to give 9.78 g (85
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Published 16 Oct 2024

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

  • Daria A. Burmistrova,
  • Andrey Galustyan,
  • Nadezhda P. Pomortseva,
  • Kristina D. Pashaeva,
  • Maxim V. Arsenyev,
  • Oleg P. Demidov,
  • Mikhail A. Kiskin,
  • Andrey I. Poddel’sky,
  • Nadezhda T. Berberova and
  • Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

Graphical Abstract
  • /prooxidant, and antiradical activity was carried out for the catechols synthesized in this work. Results and Discussion Synthesis The interaction of 3,5-di-tert-butyl-o-benzoquinone with the corresponding thiols in ethanol at room temperature under argon leads to the formation of catechol thioethers 1–3 (69
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Published 19 Sep 2024
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