Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• Medical University. Extraction and isolation The air-dried powder of the whole plants of S. sinensis (5.2 kg) was extracted three times with 95% ethanol at room temperature. The combined extracts were concentrated and yielded 423 g of a crude extract which was subjected to reversed-phase MPLC (MCI; MeOH

Mechanochemical bottom-up synthesis of phosphorus-linked, heptazine-based carbon nitrides using sodium phosphide

• Blaine G. Fiss,
• Georgia Douglas,
• Michael Ferguson,
• Jorge Becerra,
• Jesus Valdez,
• Trong-On Do,
• Tomislav Friščić and
• Audrey Moores

Beilstein J. Org. Chem. 2022, 18, 1203–1209, doi:10.3762/bjoc.18.125

• powder was then allowed to age under an argon atmosphere for 24 hours, prior to washing via centrifugation in a 3:1 by volume mixture of ethanol and deionized (DI) water. This afforded a material referred to below as g-h-PCN. Alternatively, the sample was annealed for 1 hour at 300 °C under a flow of

• quenching in water and ethanol at the end of the aging step. g-h-PCN300 featured the same three major carbon 1s peaks at 284.8, 286.2 and 288.2 eV for C=N/C=C, C=O and C–OH species, respectively, as well as the charging peak seen in g-h-PCN. In g-h-PCN300, a reduction of the C=N ratio to 37%, reduction of C

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

• Péter Kisszékelyi,
• Tibor Peňaška,
• Klára Stankovianska,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

• diethyl ether at 0 °C for 1 h gave acid 10aa in 75% yield, while complete decomposition was observed at reflux temperature after only 10 min (Table 1, entries 1 and 2). Acid 10aa did not form when the reaction was performed in ethanol, CH2Cl2, THF, DMF, or ethyl acetate at different temperatures under

• classical conditions as well as under MWI. The acid 10aa could not be formed even when 2,2'-disulfanediyldianiline was used as the starting material in DMF or ethanol at room temperature or under reflux. Thiol 8a reacted with the keto ester 9c in ethanol to form the ester 10ac with a yield of 51% and 29

• %, respectively, under different conditions (Table 1, entries 3 and 4). Reactions in ethanol under MWI and in CH2Cl2 with classical stirring at room temperature only resulted in oxidative dimerization, forming derivative 11b in 15–28% yield (Table 1, entries 5–7). Neither did the reaction proceed in ethyl acetate

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• proposed based on computational results and the main product is formed favorably following the PES via the lowest ΔG# pathway in both the gas-phase and an ethanol solvent model. DFT calculations showed that kinetic selectivity is more significant than thermodynamic selectivity for forming main products

• -acetyl-3-hydroxy-3-pyrroline-2-ones via multicomponent reactions of ethyl 2,4-dioxovalerate with aromatic aldehydes, and aniline in glacial acetic acid. These 2-pyrrolidinone derivatives were then reacted with aliphatic amines in ethanol to obtain a library of 1,4,5-trisubstituted pyrrolidine-2,3-dione

• enamine derivatives. As compared to glacial acetic acid [42], ethanol has showed to be the best solvent for the synthesis of these pyrrolidine-2,3-diones and a dramatic increase in the yield of the desired products was also observed. In addition, understanding of the reaction mechanism at the molecular

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• activity was assayed using a Total Antioxidant Capacity Assay Kit with ABTS method (Beyotime Biotechnology). Briefly, the fresh ABTS working solution was prepared by mixing ABTS stock solution with oxidant solution for an overnight reaction, and then this mixture was diluted 50 times by 80% ethanol. To

• initiate the assay reaction, 10 µL of each sample with a concentration of 1.0 mM in 80% ethanol was mixed with 200 µL of fresh ABTS working solution. After being incubated at 30 °C for 5 min, the 734 nm absorbance was measured on a Thermo Varioskan LUX Microplate reader. Trolox was used as the reference

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

• Yara Cristina Marchioro Barbosa,
• Guilherme Caneppele Paveglio,
• Claudio Martin Pereira de Pereira,
• Sidnei Moura,
• Cristiane Storck Schwalm,
• Gleison Antonio Casagrande and
• Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

• g, 1.5 mmol), 2-bromoacetophenone (0.298 g, 1.5 mmol), and absolute ethanol (2 mL) were added to a 10 mL round bottom flask. The mixture was stirred at room temperature for 5–10 min. The solid was filtered off, washed with ethyl ether, and dried in a desiccator to give the product 3a–i with adequate

Electrochemical formal homocoupling of sec-alcohols

• Kosuke Yamamoto,
• Kazuhisa Arita,
• Masashi Shiota,
• Masami Kuriyama and
• Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

• (2f and 2g). On the other hand, the reaction of 1-(4-cyanophenyl)ethanol (1h) resulted in a decrease in both the yield and the dl:meso ratio. While steric hindrance of substituents on the meta-position of the aryl moiety did not impede the present transformation (2i and 2j), the ortho-substituted

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

• Dharmendra Das,
• Akhil A. Bhosle,
• Amrita Chatterjee and
• Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

• incomplete and a mixture containing some starting material (1a), two other spots which are identified as o-monobromo (2a) as major (57%), and o-dibrominated p-cresol (3a) as minor (20%) constituents, was obtained (Table 1, entry 1). Next, the reaction mixture was ground under LAG conditions with ethanol and

On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• were made on a 0.2 mol scale and an optimal addition rate of a 12 N sodium hydroxide solution of 8.0–8.6 mmol/min was reported [32]. For our part, instead of starting the reaction at −30 °C, we used the lower temperature of −78 °C which only requires a cooling bath containing dry ice and ethanol

• (Table 2, entries 5 and 6 in comparison with entry 2). Trials using ethanol or isopropanol as a solvent (Table 2, entries 7 and 8) were not successful, plausibly because of a precipitation of the reaction medium before the end of the base addition. Trials with lithium or potassium hydroxide (Table 2

• entry 10. In a double-necked flask, phenyl glyoxal hydrate (2 g, 0.013 mol) and alanine amide hydrochloride (1.63 g, 0.013 mmol) were dispersed in methanol (35 mL). This was cooled to −78 °C using an ethanol and dry ice bath, under a calcium chloride-protected atmosphere. Then, 20% tetraethylammonium

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• of acid and carrying out the reaction at 60 °C. The formation of byproduct 1e was also observed at room temperature and attempts to trap the ethanol released in the reaction by molecular sieves did not give any improvement. Finally, we tested N-methyl-2-chloropyridinium iodide (Mukaiyama reagent) [46

Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids

• Virginija Jakubkiene,
• Gabrielius Ernis Valiulis,
• Markus Schweipert,
• Asta Zubriene,
• Daumantas Matulis,
• Franz-Josef Meyer-Almes and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 837–844, doi:10.3762/bjoc.18.84

• collected by filtration, washed with ice water and dried (compound 30 was recrystallized from a mixture of ethanol/water 1:1). In case of compound 29, after acidification, the reaction mixture was extracted with chloroform (3 × 10 mL), the organic solutions were combined, washed with brine, dried over

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• cycloadduct 3a. 3-Azabicyclo[3.1.0]hexane derivative 3a was obtained after recrystallization from MeOH in yields 67, 70, and 61%, respectively (Table 1, entries 2–4). In contrast to aprotic solvents, alcohols such as methanol (MeOH) and ethanol (EtOH) were absolutely unsuitable for carrying out this reaction

• a result of the cycloaddition reaction with cyclopropene 2m. The corresponding bis-spiro compound 5a was readily isolated in 82% yield after recrystallization from ethanol. Similarly, we succeeded in carrying out reactions between unsymmetrically 1,2-disubstituted cyclopropenes 2n, 2o and PRP (1). 1

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• electromagnetic field. Other comparisons include the Pd-mediated transfer hydrogenations using ethanol in cyclohexene (Scheme 9, case A), multicomponent reactions (Scheme 9, case B), pericyclic reactions (Scheme 10, case A) and Pd-catalyzed reactions (Scheme 10, case B) [53]. Noteworthy, packed bed fillings used

• consisting of O-allylation and Claisen rearrangement for the continuous synthesis of 2-allyl-4,6-difluorophenol (SiC = silicon carbide) [52]. Continuous flow reactions and comparison with batch reaction (oil bath). A. Pd-catalyzed transfer hydrogenations using ethanol in cyclohexene [53], B. multicomponent

Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide

• Dongming Zhang,
• Bin Lv,
• Pan Gao,
• Xiaodong Jia and
• Yu Yuan

Beilstein J. Org. Chem. 2022, 18, 647–652, doi:10.3762/bjoc.18.65

• obtained in moderate to high yields. According to the experimental results and our previous work [27][28], a possible reaction mechanism is given in Scheme 4. At first, NHPI combines with triethyl phosphite to form intermediate 4, which is the loss of ethanol to generate intermediate 5. Then, single

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• available cholic acid, which was converted to its cholyl hydrazide (1) as previously reported by us [21]. The produced cholyl hydrazide 1 was heterocyclized to 1,3,4-oxadiazole-2-thiol 2 in excellent yield (93%), via the treatment with carbon disulfide and trimethylamine in refluxing ethanol (Scheme 1) [33

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

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

Beilstein J. Org. Chem. 2022, 18, 588–596, doi:10.3762/bjoc.18.61

• in a solution of DMSO-d6. UV irradiation at a wavelength of 365 nm for 48 h in an NMR tube did not lead to any transformations of the starting pyrazole 16. Our attempts to carry out the photocyclization of pyrazole 16 in various solvents (DMF, acetonitrile, toluene, ethanol, methylene chloride

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

• Masayori Hagimori,
• Tatsusada Yoshida,
• Yasuhisa Nishimura,
• Yukiko Ogawa and
• Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

• electron-withdrawing groups [13][14][15]. Previously, we have reported various pyridine derivatives, including polysubstituted pyridines and fused pyridines, which exhibited strong fluorescence in organic solvents (ethanol and dichloromethane) [16][17][18][19], while their fluorescence in aqueous media was

• study, we used 1-methyl-4-(methylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile (1) with a methylsulfanyl group as a good leaving group. As shown in Scheme 1, the one-pot reaction of 1 with 2-aminopyridine (2a) proceeded by refluxing in ethanol for 2 h to produce the ring-fused pyridine

• –vis spectra of all compounds were recorded in ethanol (EtOH), a polar solvent, and in dichloromethane (DCM), a non-polar solvent (see Figures S15–S17 in Supporting Information File 1). The maximum absorption peaks (λmax) shifted slightly to longer wavelengths in dichloromethane. Table 2 summarizes the

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• –e [14], 4f [9], 4i [14], 4j [9], 4k [26], and 4m,n [27], and led to dienes 4a, 4g, 4h, 4l, and 4o, respectively, in yields of 52–85%. The subsequent treatment of the butadienes 4 with 2.20 equivalents of 7-chloro-4-hydrazinylquinoline in methanol or ethanol led to the formation of pyrazoles 5 in

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• (Scheme 24). Tang and co-workers described the synthesis of thiosemicarbazone 80 from menadione (10) through a condensation reaction with thiosemicarbazide (79), which was used as a ligand in the synthesis of metal complexes using different transition metals, in refluxing ethanol (Scheme 25) [125

• menadione (10) in trifluoroacetic acid under ethanol reflux conditions (Scheme 26) to synthesize acylhydrazones 81 in 63–91% yield. In view of the different structures that compounds 81a–e could adopt, after analysis by 2D NMR-NOESY spectra, it was found that all products were obtained as E-geometrical

Organocatalytic asymmetric nitroso aldol reaction of α-substituted malonamates

• Ekta Gupta,
• Narendra Kumar Vaishanv,
• Sandeep Kumar,
• Raja Krishnan Purshottam,
• Ruchir Kant and
• Kishor Mohanan

Beilstein J. Org. Chem. 2022, 18, 217–224, doi:10.3762/bjoc.18.25

• , CDCl3) δ 171.5 (C), 167.0 (C), 147.1 (C), 136.5 (C), 132.1 (CH), 132.1(CH), 128.9 (CH), 128.9 (CH), 126.1 (CH), 122.2 (CH), 122.2 (CH), 121.6 (CH), 121.6 (CH), 117.4 (C), 76.8 (C), 53.5 (CH3), 17.9 (CH3) ppm. The enantiomeric excess was determined by HPLC on a Chiralpak IC column (hexane/ethanol 90:10 v

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• ) and compounds were visualised by UV irradiation (λ = 254 nm) and/or dipping in ethanol/sulfuric acid (95:5 v/v) followed by heating. A Biotage SP4 flash chromatography system was used for purification of the protected sugars with normal phase silica (pre-packed SNAP Ultra cartridges). Deprotected

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• using 95% aqueous ethanol (15 L × 4 times × 2 h at room temperature) with ultrasonic assistance. The combined extracts were filtered and evaporated under reduced pressure to yield a green residue (350.6 g). The crude extract was suspended in distilled H2O (2 L) and successively partitioned with n-BuOH

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• . We mainly focused on the synthesis under green aspects and towards a high product diversity. We initially chose three green solvents with a relatively low boiling point, ethanol, water, and acetone, respectively, as a reaction medium. A series of reactions was examined in these solvents, using an

• temperature. In the ultrasonication procedure, the reaction was started at room temperature, and after completion of the reaction, the final temperature of the solution was found to be 40 °C. Among the solvents, ethanol afforded the highest yield under sonication within a very short reaction time. When we

• further increasing this quantity did not result in an enhanced yield. As such, the optimized conditions were sonication for 15 min in ethanol using 30 mg of the Ni–chitosan NPs (Table 2, entry 17). The optimization studies using this standard amount of catalyst are summarized in Table 2. Substrate scope

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

• Malcolm J. D’Souza and
• Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

• -methyl derivative, 0.0146 min−1 for the parent compound, and 0.044 min−1 for the m-NO2 derivative. A change of solvent to 47.5% ethanol/52.5% water led to very similar behavior with the corresponding specific rates being 0.0287, 0.0313, and 0.058 min−1. In modern terminology, this would suggest a close

• value of +0.82 for the para-methyl derivative and of +0.71 for the meta-nitro derivative. and, for the study in 47.5% ethanol/52.5% water the corresponding values are +0.22 and +0.38, respectively. These small reaction constant ρ values depend only on the type of reaction but not on the substituent used

• aqueous dioxane, aqueous acetone, methanol/acetone, and ethanol/acetone, the p-NO2 (strongest electron-withdrawing influence) was always reacting faster than the parent and the other two derivatives and the overall behavior in a Hammett equation treatment indicated that all were reacting by an SN2 pathway

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• material in the synthesis of the other isomer of β-amino acid 6. The ring-opening reaction of 7 with HCl(g) in MeOH resulted in a mixture of products 8 and 9 in a 9:1 ratio (1H NMR). The product 8 in the reaction mixture was purified by recrystallization from ethanol/ether, but all attempts to purify the