Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers

• İlknur Polat,
• Selçuk Eşsiz and
• Emine Salamci

Beilstein J. Org. Chem. 2026, 22, 547–556, doi:10.3762/bjoc.22.40

• . Purification by silica gel column chromatography eluting with EtOAc/hexane 5:95 provided azidol 7 [23] as slightly yellow oil (2.47 g, 14.77 mmol, 92%, lit. [23] 71%). 1H NMR (400 MHz, CDCl3) δ 5.69–5.61 (m, 1H), 5.60–5.52 (m, 1H), 3.79–3.65 (m, 2H), 2.56–2.36 (m, 2H), 2.27–2.09 (m, 4H), 1.81–1.67 (m, 2H); 13C

Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

• Horst Weber,
• Kim-Thao Tran-Cong,
• Bernhard Mayer,
• Guido J. Reiss,
• Iryna S. Konovalova,
• Marc S. Appelhans,
• Kenneth R. Wood and
• Claus M. Passreiter

Beilstein J. Org. Chem. 2026, 22, 535–546, doi:10.3762/bjoc.22.39

• 5 (CAS: 59582-20-6) [20] as a beige colored viscous oil, which was used without further purification. HRESIMS m/z: [M + H]+ calcd. for C18H23O4, 303.1591; found, 303.1596. 1H NMR data in CDCl3 (δ ppm) 1.43 (s, 3H, 2-CH3), 1.56 (s, 3H, 4’-CH3), 1.67 (s, 3H, 4’-CH3), 1.70/1.85 (m, 2H, H-2’), 2.10/2.15

Modern synthetic pathways towards eribulin and its subunits

• Sebastian Dominik Graf

Beilstein J. Org. Chem. 2026, 22, 495–526, doi:10.3762/bjoc.22.37

• -workers assembled 276 via simple ring opening of 275`s oxetane moiety and no cooling and intermediate purification were necessary. These practical improvements are particularly important for the large-scale synthesis of 1. Furthermore, every step up to 292 was carried out in kg amounts using only

Structural reassignment of compound 968, an allosteric glutaminase inhibitor

• Lindsey A. Albertelli,
• Sainabou Jallow,
• Chun Li and
• Scott M. Ulrich

Beilstein J. Org. Chem. 2026, 22, 455–460, doi:10.3762/bjoc.22.33

• diffractometer. Nuclear magnetic resonance spectra were recorded on a JEOL ECX400 spectrometer. Glutaminase assays were measured on a Tecan Infinite M nano spectrophotometer. Reagents and solvents for chemical synthesis were used without additional purification. Chemical synthesis 3-Bromo-4

• employed for the final data presentation and structure plots [35]. The crystal data have been deposited in the Cambridge Crystallographic Data Centre, deposition number CCDC 2426481. Enzymatic assay Expression and purification of the GAC isoform of GLS1 Overnight cultures of BL21(DE3) strains carrying GAC

A facile and practical method for the synthesis of trans-(±)-taxifolin and its derivatives via Darzens reaction

• Bo Peng,
• Panpan Yang,
• Maaz Khan,
• Xiaotong Lin,
• Jiang Wu,
• Peng Fu and
• Qingqing Wu

Beilstein J. Org. Chem. 2026, 22, 443–450, doi:10.3762/bjoc.22.31

• [6] (Figure 1). Taxifolin can be obtained by extraction from natural plants [7][8][9], however, this is not economically viable due to the complicated extraction and purification process and low natural abundance of taxifolin. Enzymatic synthesis [10][11][12][13][14] is another method employed to

• purification was required after post-treatment. The formed silyl enol ether was then reacted with NBS (1.1 equiv) in a mixed solvent of THF and PBS buffer solution (pH 7.2) to give compound 2 with a total yield of 91% over the successive two steps. Darzens reaction of compound 2 (10.05 g) with benzaldehyde 3a

• (1.2 equiv) was performed in CH3CN, using t-BuOLi (1.2 equiv) as base in the presence of a catalytic amount of ZnCl2. Due to the high efficiency of the reaction, no purification of product (±)-4a by column chromatography was necessary after post-treatment and the product could be directly used in the

Synthesis and anti-cancer activity of naphthalimide–organylselanyl conjugates

• Rajkumar Ravi and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2026, 22, 416–435, doi:10.3762/bjoc.22.29

• carried out under a nitrogen atmosphere using standard Schlenk line methods. Reagents and solvents were obtained from GK Life Sciences Pvt. Ltd. and used without further purification unless otherwise stated. Thin-layer chromatography (TLC) was performed on silica-gel-coated aluminium sheets (silica gel 60

Cone p-aminocalix[4]arenes enriched with ‘clickable’ alkyne or azide functionalities

• Ilia Korniltsev,
• Vasily Bazhenov,
• Alexander Gorbunov,
• Dmitry Cheshkov,
• Stanislav Bezzubov,
• Vladimir Kovalev and
• Ivan Vatsouro

Beilstein J. Org. Chem. 2026, 22, 399–415, doi:10.3762/bjoc.22.28

• all cases, p-aminocalix[4]arenes were obtained as the readily cleavable tert-butoxycarbonyl (Boc) derivatives, which was crucial for certain transformation and purification steps. To confirm the functionalization capabilities of the five obtained multifunctional calixarenes, they were reacted with

Dialkylaminoalkylation of β-ketosulfones via ring-opening of 3-sulfonylpyrrolidines

• Evgeny M. Buev,
• Alexander V. Pavlushin,
• Vladimir S. Moshkin and
• Vyacheslav Y. Sosnovskikh

Beilstein J. Org. Chem. 2026, 22, 383–389, doi:10.3762/bjoc.22.26

• by adding the alkyl halide directly to the cooled reaction mixture of the formed pyrrolidine without its isolation and purification, that provided higher yields of the quaternary compounds 3 rather than step by step approach. Further, we focused our attention on the search for the reaction conditions

A mild and atom-efficient four-component cascade strategy for the construction of biologically relevant 4-hydroxyquinolin-2(1H)-one derivatives

• Dmitrii A. Grishin,
• Kseniia I. Sharkovskaia,
• Ilya G. Kolmakov,
• Daria A. Ipatova,
• Rostislav A. Petrov,
• Nikolai D. Dagaev,
• Dmitry A. Skvortsov,
• Maria G. Khrenova,
• Valeriy V. Andreychev,
• Sergei A. Evteev,
• Yan A. Ivanenkov,
• Roman L. Antipin,
• Olga А. Dontsova and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2026, 22, 244–256, doi:10.3762/bjoc.22.18

• products were also obtained via the four-component reaction using non-nucleophilic acetonitrile as solvent. However, this method requires subsequent purification by preparative chromatography, and, as noted, pyranoquinolines 14a–c readily undergo alcoholysis on silica columns with methanol-containing

Configuration–packing synergy enabling integrated crystalline-state RTP and amorphous-state TADF

• Ruiyan Wang and
• Yunan Wu

Beilstein J. Org. Chem. 2026, 22, 224–236, doi:10.3762/bjoc.22.16

• without further purification. Instruments and measurements Low-resolution mass spectra were recorded on a DSQ electron-impact (EI) mass spectrometer. High-resolution mass spectra (HRMS) were acquired on a Thermo MAT95XP instrument using fast atom bombardment (FAB) ionization. 1H and 13C NMR spectra were

Synthesis of diaryl phosphates using phytic acid as a phosphorus source

• Kazuya Asao,
• Seika Matsumoto,
• Haruka Mori,
• Riku Yoshimura,
• Takeshi Sasaki,
• Naoya Hirata,
• Yasuyuki Hayakawa and
• Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

• esters could be slightly improved by using a catalytic amount of 1-butylimidazole; however, in the present work, a catalyst was not employed to simplify the purification step. The reaction temperature in this process should have been set to 230 °C. However, at this temperature, a burnt black material was

• recovery of 4.2% based on the total P analysis data. Considering the losses that occurred during the purification steps, these results were consistent with the fact that 100 g of rice bran contained approximately 6 g of phytic acid [1][2][3]. Subsequently, the isolated phytate was desalted using a cation

• ). The residue was washed with methanol and dried under vacuum overnight. Finally, 2.52 g of the crude sodium phytate was obtained as a white solid. Purification of extracted phytic acid Well-conditioned DOWEX 50W × 2 100–200 mesh (H) cation exchange resin (Dow Chemical Co., Midland, MI, USA) (60 mL) was

Streptoquinolines A and B, new antibacterial meroterpenoids produced by Streptomyces sp. TMPU-A0679

• Akiho Yagi,
• Hitomi Tomura,
• Ami Konno and
• Ryuji Uchida

Beilstein J. Org. Chem. 2026, 22, 185–191, doi:10.3762/bjoc.22.12

• shaker (180 rpm) at 27 °C for 7 days using a malt extract-based production medium. Harvested mycelia (1.0 L) were extracted with acetone and ethyl acetate, and purification was guided by antibacterial activity against VRE. The crude extract (922 mg) was subjected to ODS column chromatography followed by

Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH

• Adrian G. Rossebø,
• Hannah G. Kolberg,
• Anders E. Tønder,
• Louise Kjaerulff,
• Poul Erik Hansen,
• Karla A. Frydenvang,
• Jesper Østergaard and
• Jesper L. Kristensen

Beilstein J. Org. Chem. 2026, 22, 175–184, doi:10.3762/bjoc.22.11

• aqueous Na2CO3. The layers were separated, the organic phase collected, and the aqueous phase was further extracted with dichloromethane (3 × 25 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, evaporated in vacuo, and deposited on Celite. Purification by automated flash column

A new synthesis of Tyrian purple (6,6’-dibromoindigo) and its corresponding sulfonate salts

• Holly Helmers,
• Mark Horton,
• Julie Concepcion,
• Jeffrey Bjorklund and
• Nicholas C. Boaz

Beilstein J. Org. Chem. 2026, 22, 167–174, doi:10.3762/bjoc.22.10

• advantages of inexpensive starting reagents, operationally simple reactions, and minimal purification of intermediates. Moreover, this work reports the successful sulfonation of 6,6’-dibromoindigo, producing water-soluble derivatives of this historically relevant dye. Keywords: 6,6’-dibromoindigo; dye

• methodology of Keinan et al. [12], compound 5 was nitrated with fuming nitric acid in a mixture of glacial acetic acid and sulfuric acid. As shown in Scheme 3, this reaction yielded a mixture of 3 and 4-bromo-3-nitrotoluene (7) in a ≈3:1 ratio. Purification via column chromatography was successful in removing

• addition of 1.2 equivalents of triethylamine mediated the formation of 4 in moderate yield, as shown in Scheme 5B (57% isolated, 67% based on NMR). The crude product was sufficiently pure (84 wt % by quantitative NMR) to carry on without purification, but further purification was possible by

Design and synthesis of an axially chiral platinum(II) complex and its CPL properties in PMMA matrix

• Daiki Tauchi,
• Sota Ogura,
• Misa Sakura,
• Kazunori Tsubaki and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2026, 22, 143–150, doi:10.3762/bjoc.22.7

• optoelectronic applications. Experimental General information All reagents and solvents were of commercial reagent grade and used without further purification. Dichloromethane for spectroscopy was purchased from FUJIFILM Wako Pure Chemical Corporation. All compounds were identified by 1H , 13C NMR and ESI-MS. 1H

Highly electrophilic, gem- and spiro-activated trichloromethylnitrocyclopropanes: synthesis and structure

• Ilia A. Pilipenko,
• Mikhail V. Grigoriev,
• Olga Yu. Ozerova,
• Igor A. Litvinov,
• Darya V. Spiridonova,
• Aleksander V. Vasilyev and
• Sergey V. Makarenko

Beilstein J. Org. Chem. 2026, 22, 123–130, doi:10.3762/bjoc.22.5

• . Visualization was performed under UV light (λ 254 nm). Reagents were obtained from commercial suppliers and used without further purification unless otherwise noted. X-ray crystallography. X-ray diffraction analysis of the structure 2, 3, 9a, and 9b was performed on a Rigaku 'SuperNova, Single source at offset

Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review

• Daniel S. Müller

Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1

• discrepancy to product degradation during purification on neutralized silica gel (1% NEt₃) or neutral alumina. However, this hypothesis was not experimentally verified, as no control experiment involving the passage of a pure, non-volatile alkenyl chloride through the purification media was reported to assess

• compound loss or degradation at the purification step. 1.2 Exchange reactions This chapter deals with exchange reactions, meaning that a given substituent on the alkene is formally exchanged for chlorine. The reactions are very different from each other in terms of mechanism and for a full discussion the

One-pot synthesis of ethylmaltol from maltol

• Immanuel Plangger,
• Marcel Jenny,
• Gregor Plangger and
• Thomas Magauer

Beilstein J. Org. Chem. 2025, 21, 2755–2760, doi:10.3762/bjoc.21.212

• ). Purification with flash column chromatography provided analytically pure ethylmaltol (1), which, however, displayed an off-white/yellowish color. A final vacuum distillation yielded purely white ethylmaltol (1) consistent with commercial samples. The ethylmaltol (1) thus produced was analyzed by the Central

Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides

• Alexander S. Budnikov,
• Nikita E. Leonov,
• Michael S. Klenov,
• Andrey A. Kulikov,
• Igor B. Krylov,
• Timofey A. Kudryashev,
• Aleksandr M. Churakov,
• Alexander O. Terent’ev and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2025, 21, 2739–2754, doi:10.3762/bjoc.21.211

• purification. Ammonium dinitramide (ADN) [106], 2-nitro-2-nitrosopropane (1a) [107], 1-nitro-1-nitrosocyclopentane (1b) [108], 1-nitro-1-nitrosocyclohexane (1c) [109], 2-nitro-2-nitroso-1,3-diphenylpropane (1e) [110], 2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane (1f) [111], methyl 2-nitro-2-nitrosopropanoate (1g

Tandem hydrothiocyanation/cyclization of CF₃-iminopropargyl alcohols with NaSCN in the presence of AcOH

• Ruslan S. Shulgin,
• Ol’ga G. Volostnykh,
• Anton V. Stepanov,
• Igor’ A. Ushakov,
• Alexander V. Vashchenko and
• Olesya A. Shemyakina

Beilstein J. Org. Chem. 2025, 21, 2694–2702, doi:10.3762/bjoc.21.207

• available starting materials were used without further purification. CF3/n-C3F7-substituted iminopropargyl alcohols 1 were prepared according to published methods [31][32]. The structures of synthesized products have been proven by 1H, 13C and 2D (1Н,13С HMBC) NMR, 19F NMR techniques, as well as IR spectra

Recent advancements in the synthesis of Veratrum alkaloids

• Morwenna Mögel,
• David Berger and
• Philipp Heretsch

Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206

• transformation carried out in one flask terminated by a purification [11]. Nevertheless, to point out reaction telescoping (i.e., performing several reactions in one flask by sequentially adding reagents, including solvent-swaps) we opted for a visual representation indicated by black frames around the boxes

Synthesis of new tetra- and pentacyclic, methylenedioxy- and ethylenedioxy-substituted derivatives of the dibenzo[c,f][1,2]thiazepine ring system

• Gábor Berecz,
• András Dancsó,
• Mária Tóthné Lauritz,
• Loránd Kiss,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2645–2656, doi:10.3762/bjoc.21.205

• numbers: CCDC 2470493 (20e), CCDC 2470491 (21g), CCDC 2470492 (23a), CCDC 2470490 (25), CCDC 2470489 (26), CCDC 2472402 (27). All reagents were purchased from commercial sources and were used without further purification. Reactions were followed by analytical thin-layer chromatography on silica gel 60

Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids

• Luan A. Martinho,
• Victor H. J. G. Praciano,
• Guilherme D. R. Matos,
• Claudia C. Gatto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2025, 21, 2618–2636, doi:10.3762/bjoc.21.203

• condensation reactions involving rhodanine derivatives (26 examples). In addition, it requires a lower catalyst loading (10 mol %) and eliminates the need for further purification steps. EDDA has also been employed in reactions for the synthesis of heterocyclic compounds such as tetrahydroquinolines [67

Efficient solid-phase synthesis and structural characterization of segetalins A–H, J and K

• Liangyu Liu,
• Wanqiu Lu,
• Quanping Guo and
• Zhaoqing Xu

Beilstein J. Org. Chem. 2025, 21, 2612–2617, doi:10.3762/bjoc.21.202

• purification, all cyclopeptides were obtained in 45–70% isolated yields. Structural identities were confirmed by HRESIMS, NMR, and HPLC (>95% purity). Circular dichroism (CD) spectroscopy revealed distinct secondary structures, including β-sheets (1, 2, 3, 4, 7, 8, 10) and α-helical elements (5, 6). This

Silica gel with covalently attached bambusuril macrocycle for dicyanoaurate sorption from water

• Michaela Šusterová and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2025, 21, 2604–2611, doi:10.3762/bjoc.21.201

• to SG not only by electrostatic interactions but also covalently, the BU1 synthesis is straightforward lacking difficult and time-consuming purification, and it is obtained in relatively high yield over 60%. Once BU1 was prepared, its covalent attachment on the surface of SG was achieved in two steps

• and used without further purification. Dodecakis(5-carboxypentyl)bambus[6]uril (BU1) was synthesized according to a previously published procedure [13]. Infrared spectra were recorded with an Alpha spectrophotometer (Bruker). Thermogravimetric analyses were done with a Netzsch STA 449C Jupiter and