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Search for "ethanol" in Full Text gives 751 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium

  • Dāgs Dāvis Līpiņš,
  • Andris Jeminejs,
  • Una Ušacka,
  • Anatoly Mishnev,
  • Māris Turks and
  • Irina Novosjolova

Beilstein J. Org. Chem. 2024, 20, 675–683, doi:10.3762/bjoc.20.61

Graphical Abstract
  • % purity) [26] provided a more selective reaction, no water-based work-up was needed and the pure product was obtained by simple recrystallization from ethanol in yields up to 88%. The oxidation step thiol → sulfoxide was fast and full conversion to the intermediate was achieved in one hour for most
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Published 28 Mar 2024

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

  • Luan A. Martinho and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

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  • is known for its chemical and thermal stability. Herein, we report a straightforward approach to the GBB-3CR using HPW as catalyst in ethanol under microwave (μw) heating. This convenient environmentally benign methodology is broad in scope, provides the heterobicyclic products in high yields (up to
  • catalyst in ethanol under microwave (μw) heating. This convenient environmentally benign methodology is broad in scope, provides the heterobicyclic products in high yields (up to 99%), with a low catalyst loading (2 mol %) in only 30 minutes. Results and Discussion A search in the literature revealed a
  • temperature or in the reaction time were checked, however, with no benefit in the yields (Table 1, entries 9–12). Accordingly, with the established optimal conditions of 2 mol % of HPW, 120 °C, and 30 min, other solvents were tested, and ethanol was found to give similar results (Table 1, entry 13). For being
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Published 19 Mar 2024

Chemical and biosynthetic potential of Penicillium shentong XL-F41

  • Ran Zou,
  • Xin Li,
  • Xiaochen Chen,
  • Yue-Wei Guo and
  • Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

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  • fermentation products, showed a lower number and abundance in the PDB medium than in the XISR I and XISR III media, as illustrated in Figure 1. Consequently, we chose XISR I and XISR III media for further fermentation. The fermentation broth was exhaustively extracted with ethanol, after which the ethanol
  • hydroxamic acid 6 µM; sodium butyrate 6 µM). Extraction The mycelium was separated from the fermentation broth using a centrifuge and subsequently extracted with ethanol in a 1:1 ratio using ultrasound, three times for 20 minutes each. The combined organic solvents were dried with a rotary evaporator to
  • yield an ethanol extract. This extract was further processed with ethyl acetate (EtOAc) three times. The combined EtOAc phase was then dried using a rotary evaporator to obtain the EtOAc extract, which was stored at −80 °C until further purification process. The above fermentation broth was adsorbed
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Published 15 Mar 2024

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

  • Michael O. Akintubosun and
  • Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

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  • . Reactions for thin-layer chromatography analysis were carried out using the same general reaction conditions reported above. Six μL of each reaction were spotted on the TLC silica gel 60 F254 (Sigma) and run with a solvent system containing butanol/ethanol/water 5:4:3. The TLC was stained using a solution
  • containing 3.7 mL p-anisaldehyde, 135 mL ethanol, 5 mL sulfuric acid, and 1.5 mL glacial acetic acid. Light pink spots were observed following heating at 105 °C. Kinetics assays were carried out by varying concentrations of substrate (myo-inositol or scyllo-inositol) from 1 mM to 60 mM with 1 μM Hyg17 and 10
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Published 14 Mar 2024

Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides

  • Alexander Yanovich,
  • Anastasia Vepreva,
  • Ksenia Malkova,
  • Grigory Kantin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48

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  • 1H NMR spectroscopy data, one of its components was the product of the migration of the double bond of the benzylidene fragment into the succinimide cycle – compound 22. Finally, a compound with a longer side chain 24, obtained from 2-(2-bromoethoxy)ethanol (23), underwent exclusively isomerization
  • )ethanol. In the latter case, the predominant process was found to be the base-promoted migration of the C=C bond of the arylidene fragment into the cycle. Examples of biologically active compounds and natural products based on THF/THP spiro-conjugates with pyrrolidine rings. DAS spirocyclizations reported
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Published 11 Mar 2024

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

  • Periklis X. Kolagkis,
  • Eirini M. Galathri and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

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  • involves gradually adding titanium tetra-n-butoxide to a solution of deionized water in ethanol and calcinating it to form the desired nanocompounds. 10 mol % of the nano-TiO2 heated at 80 °C, provided an optimum yield of 95% for the reaction of indole with benzaldehyde, under solvent-free conditions after
  • Fe3O4@PEG-SO3H complex were added in ethanol for a time period of 5 to 10 minutes, yielding 88–98% of isolated product with only aromatic aldehydes showing a meaningful reactivity (Scheme 23) [122]. In 2022, Boroujeni et al. employed a Cu(II) complex coated in Fe3O4@SiO2 nanoparticles which worked as an
  • efficient nanocatalyst for the synthesis of BIMs in a catalytic amount of 30 mg at 80 °C [123][124]. A mixture of water and ethanol (1:1) was discovered to be the optimum solvent with reaction times starting from 11 to 30 minutes, while approaching yields ranging from 92% for aliphatic aldehydes to 97% for
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Published 22 Feb 2024

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

  • Eugeny Ivakhnenko,
  • Vasily Malay,
  • Pavel Knyazev,
  • Nikita Merezhko,
  • Nadezhda Makarova,
  • Oleg Demidov,
  • Gennady Borodkin,
  • Andrey Starikov and
  • Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

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  • conditions. The reactions proceed readily in refluxing acidified (pKa = 1–5) ethanol solutions of the amine hydrochlorides to give 2-monosubstituted derivatives of 3H-phenoxazin-3-ones in a moderate yield [10][17]. In the present work, we intended to explore the reaction of 3H-phenoxazin-3-ones with aromatic
  • fluorescence quantum yield was determined relative to quinine bisulfate in 0.05 M H2SO4 as standard (ΦF = 0.52, excitation at 365 nm for 5a–c and 6a,b) [26] and cresyl violet perchlorate in ethanol (ΦF = 0.54, excitation at 510 nm for 10c) [27]. Mass spectrometric analysis was performed on a Bruker UHR-TOF
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Published 21 Feb 2024

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

  • Aissam Okba,
  • Pablo Simón Marqués,
  • Kyohei Matsuo,
  • Naoki Aratani,
  • Hiroko Yamada,
  • Gwénaël Rapenne and
  • Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

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  • structure induced by the embedded heteropine ring. By way of example, the solubility of SeO-doped seco-HBC 29c is more than 100-fold higher than pristine HBC carrying four tert-butyl groups in both dichloromethane and ethanol. Ring contraction was next attempted on the series of heteropines synthesized
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Published 15 Feb 2024

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

  • Milandip Karak,
  • Cian R. Cloonan,
  • Brad R. Baker,
  • Rachel V. K. Cochrane and
  • Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

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  • -phosphite intermediate was then oxidized with hydrogen peroxide to yield dibenzyl α-phosphate 6, achieving an overall yield of 89% for these two steps. Removal of the 2-(phenylsulfonyl)ethanol protecting group in compound 6 was successfully achieved through treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene
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Published 06 Feb 2024

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

  • Pengcheng Li,
  • Daniel Kowalczyk,
  • Johannes Liessem,
  • Mohamed M. Elnagar,
  • Dariusz Mitoraj,
  • Radim Beranek and
  • Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

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  • voltage of 15 kV. To prepare the sample for SEM imaging, a few milligrams of the Pt-PCN material were dispersed in 1.0 mL of ethanol using sonication for 5 min. Subsequently, a thin film of the sample was obtained by drop-casting a few microliters of the suspended sample onto a conductive Cu foil
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Published 16 Jan 2024

Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

  • Lorenzo Catti,
  • Shinji Aoyama and
  • Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

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  • , amphiphiles PA-OCH3 and PA-OH were synthesized by reacting prePA under neat conditions with 1-(2-bromoethoxy)-2-(2-methoxyethoxy)ethane (67% yield over 2 steps after ion-exchange) and 2-[2-(2-chloroethoxy)ethoxy]ethanol (42% yield), respectively (Figure 2b). Imidazole-functionalized amphiphile PA-Im was
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Published 08 Jan 2024

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

  • Pavel S. Silaichev,
  • Tetyana V. Beryozkina,
  • Vsevolod V. Melekhin,
  • Valeriy O. Filimonov,
  • Andrey N. Maslivets,
  • Vladimir G. Ilkin,
  • Wim Dehaen and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

Graphical Abstract
  • temperature. A similar yield of the target product 3a was obtained by the reaction in ethanol in the presence of NaOH at 0 °С (entry 11 in Table 1). The latter conditions can be an alternative for the synthesis of compounds 3. Synthesis of N-heteroaryl amidines 3 We hypothesized that both 3,3
  • of the substituents in azides 2 was observed. We assume the higher yield of pyrimidine containing triazoles 3a–k by their lower solubility in 1,4-dioxane compared with the solubility of azole containing compounds 3l–s in both 1,4-dioxane and ethanol. With regard to the scope of diaminoacrylonitriles
  • hydroxide, freshly prepared from sodium hydroxide (20 mg, 0.5 mmol) and ethanol (2 mL), and the resulting mixture was stirred at room temperature for 5–10 min. Then, the mixture was cooled to 0 °C, the corresponding azide 2 (0.5 mmol) was added and the resulting mixture were stirred for 30 min, after which
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Published 05 Jan 2024

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

  • Recep Isci and
  • Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

Graphical Abstract
  • organic layer was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography eluting with a mixture of n-hexane/CH2Cl2 3:1 and then crystallized from ethanol to give the title compound DMB-TT-TPA (8) as a yellow powder
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Published 07 Dec 2023

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

  • Gyula Dargó,
  • Dóra Erdélyi,
  • Balázs Molnár,
  • Péter Kisszékelyi,
  • Zsófia Garádi and
  • József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

Graphical Abstract
  • acid ester 9 was hydrolyzed under basic conditions in an ethanol/water mixture. After the reaction, the pH of the mixture was adjusted to 4 with hydrochloric acid, which resulted in the precipitation of the product 10 in excellent yield (95%). Next, carboxylic acid 10 was converted into the
  • polar solvent, i.e., methanol, to its solution. The main requirement for the polar solvent is that it should not dissolve the catalyst while it should completely dissolve the product. Therefore, we investigated the solubility of the Michael adduct 14 in methanol, ethanol, propan-2-ol, Patosolv® (a
  • mixture of 85% of ethanol and 15% of propan-2-ol), and acetonitrile. The highest solubility of 14 was found in acetonitrile (63 mg mL−1) and methanol (17 mg mL−1). In both of these solvents, a low solubility of the lipophilic catalyst 2 was measured (<0.5 mg mL−1). Based on these results, acetonitrile was
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Published 24 Nov 2023

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

  • Dayanne Martins,
  • Roberta Lamosa,
  • Talis Uelisson da Silva,
  • Carolina B. P. Ligiero,
  • Sérgio de Paula Machado,
  • Daphne S. Cukierman and
  • Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

Graphical Abstract
  • mmol, 0.226 g) and 2-hydroxy-3-methylbenzaldehyde (MBA, 1.0 mmol, 0.136 g), for hdz-CH3, or 2-hydroxy-3-nitrobenzaldehyde (NBA, 1.0 mmol, 0.167 g), for hdz-NO2, in 20 mL ethanol (Scheme 2). One drop of concentrated HCl was added to the mixture as a catalyst. After stirring at 50 °C for 4 h, the mixture
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Published 10 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

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  • demonstrated interesting, reversible, solvent-directed macrocycle-to-macrocycle interconversions. The transformations between the [1 + 1] 36 and [2 + 2] 37 macrocycles were governed by the solvent. The smaller monomeric 36 was obtained as the major product in chloroform, methanol, and ethanol. The conversion
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Published 27 Oct 2023
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  • (cavity) and the other directional due to hydrogen bonds (hydroxy groups), leads to the formation of these complexes. Results and Discussion The addition of two equivalents of sec-amines to an ethanol solution of R[4]A results in the formation of a crystalline precipitate with limited solubility in non
  • dipropylamine and diisopropylamine, complexes with a stoichiometry of 1:2 are formed (i.e., 1 molecule of R[4]A binding to 2 molecules of dipropylamine or diisopropylamine). Regardless of the quantity of amine added to the solution of R[4]A in ethanol (4 equiv, 2 equiv, and 1 equiv, respectively), a 1:2
  • substituents with R[4]A in ethanol were synthesized. The composition of the complexes was determined based on the integration of amine proton signals in the 1H NMR spectra. For small molecule sec-amines such as N,N-dimethylamine, N,N-diethylamine, and cyclic amines (pyrrolidine, piperidine, morpholine, N
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Published 29 Sep 2023

Synthesis of ether lipids: natural compounds and analogues

  • Marco Antônio G. B. Gomes,
  • Alicia Bauduin,
  • Chloé Le Roux,
  • Romain Fouinneteau,
  • Wilfried Berthe,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

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Published 08 Sep 2023

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal

  • Alessandro Brusa,
  • Debora Iapadre,
  • Maria Edith Casacchia,
  • Alessio Carioscia,
  • Giuliana Giorgianni,
  • Giandomenico Magagnano,
  • Fabio Pesciaioli and
  • Armando Carlone

Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92

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  • acetaldehyde have been reported [20][21][22][23][24]. The safety and handling problems associated with acetaldehyde can be solved by synthetic equivalents that can be generated in situ through different paths. Some examples are represented by vinyl acetate [25], silyl vinyl ethers [26], ethanol, pyruvic acid
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Published 24 Aug 2023

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

  • Chandra Sekhar Tekuri,
  • Pargat Singh and
  • Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

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  • -tetraarylporphyrins 1 were synthesized from the corresponding 2-nitro-meso-tetraarylporphyrins in two steps by following the literature procedure [42]. The first step involved an amination of copper(II) 2-nitro-meso-tetraarylporphyrins by using 4-amino-4H-1,2,4-triazole in the presence of NaOH in refluxing ethanol
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Published 11 Aug 2023

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

  • Valeriy O. Filimonov,
  • Alexandra I. Topchiy,
  • Vladimir G. Ilkin,
  • Tetyana V. Beryozkina and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

Graphical Abstract
  • molecule cyano- and thioamide groups, as well as a fragment of enamine, each in principle being capable of interaction with hydrazine (3a) (Figure 2). First, we have studied the reaction of thioamides 1a–c with hydrazine (3a). It was found that the reaction proceeds smoothly in ethanol at 80 °C to form 3,5
  • elimination of hydrogen sulfide (Scheme 2). Thus, we have shown that when 2-cyanothioacetamides 1a–c react with hydrazine hydrate (3a) in ethanol, both groups (thioamide and cyano) interact with hydrazine with the elimination of hydrogen sulfide and the formation of 3,5-diaminopyrazoles 4a–c (Scheme 2). It
  • -aryl-5-amino-4-thiocarbamoyl pyrazoles 6a–f with yields of 63–86% (Scheme 3). However, we have found that when replacing hydrazine hydrate with arylhydrazines and arylsulfonylhydrazines, the reaction in ethanol was not detected, neither at room temperature nor at reflux. The progress was achieved only
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Published 08 Aug 2023

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

  • Damiano Diprima,
  • Hannes Gemoets,
  • Stefano Bonciolini and
  • Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

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  • resulted in a significant reduction in kinetics and selectivity (Table 1, entry 3). Other more green and biobased solvent alternatives, such as ethanol [36], can effectively replace the acetonitrile (for the complete scope of solvents, please consult Supporting Information File 1, Table S2), but reaction
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Published 31 Jul 2023

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

  • Xiu-Yu Chen,
  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

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  • reaction was carried out in common solvents such as ethanol, methanol, dichloromethane, and chloroform at room temperature for two hours. The expected isoquinolino[1,2-f][1,6]naphthyridine derivative 4a was successfully obtained in 35%, 40% 70% and 65% yields, respectively (Table 1, entries 1–4). The
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Published 29 Jun 2023

First synthesis of acylated nitrocyclopropanes

  • Kento Iwai,
  • Rikiya Kamidate,
  • Khimiya Wada,
  • Haruyasu Asahara and
  • Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2023, 19, 892–900, doi:10.3762/bjoc.19.67

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  • substrates, almost equal amounts of diastereomers were formed. Whereas 4b was isolated by recrystallization of the reaction mixture from ethanol, the other adducts 4c–g were easily isolated by column chromatography. For comparison with previously reported results, adduct 4b, derived from acetylacetone (3b
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Published 21 Jun 2023

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

  • Lukáš Marek,
  • Jiří Váňa,
  • Jan Svoboda and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

Graphical Abstract
  • 70–95%). The presence of a base and the type of solvent seems to be an important factor for the reaction course. In toluene, ionic liquid or in refluxing ethanol without a base [16][19][20] or in the presence of weakly basic pyridine [17][18][21] (pKa = 5.23 in water, 3.4 in DMSO, 3.3 in DMF, and
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Published 09 Jun 2023
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