Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis

• Nicolas Kratena,
• Nicolas Heinzig and
• Peter Gärtner

Beilstein J. Org. Chem. 2026, 22, 289–343, doi:10.3762/bjoc.22.21

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

• (SHIMADZU, Kyoto, Japan) and JMS GC-mate II (JEOL, Tokyo, Japan) instruments. The melting points were determined using a Q-200 differential scanning calorimeter (TA Instruments, New Castle, DE, USA). The NMR spectra were recorded in a deuterated solvent (D2O, methanol-d4 or dimethyl sulfoxide (DMSO)-d6

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

• Scheme 5A, dimethyl sulfoxide (DMSO) did not react with the benzyl bromide and instead only returned the starting material. The addition of 1.2 equivalents of silver nitrate promoted the substitution of the benzyl bromide with DMSO to yield an alkoxysulfonium ion 8 [22]. Following substitution, the

Effect of a photoswitchable rotaxane on membrane permeabilization across lipid compositions

• Udyogi N. K. Conthagamage,
• Lilia Lopez,
• Zuliah A. Abdulsalam and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2498–2512, doi:10.3762/bjoc.21.192

• egg yolk phosphatidylcholine (EYPC), Dipalmitoylphosphatidylcholine (DPPC), and cholesterol, all obtained from Avanti Lipids. All buffer solutions were prepared using Milli-Q Water from a Barnstead™ Water Purification System. Molecular biology grade dimethyl sulfoxide was used for stock solutions of

The high potential of methyl laurate as a recyclable competitor to conventional toxic solvents in [3 + 2] cycloaddition reactions

• Ayhan Yıldırım and
• Mustafa Göker

Beilstein J. Org. Chem. 2025, 21, 2389–2415, doi:10.3762/bjoc.21.184

• were measured using Bruker ultrashield plus biospin 400 MHz NMR spectrometer and chloroform-d (CDCl3) or hexadeuterodimethyl sulfoxide (DMSO-d6) as a solvent. Chemical shifts (δ) are reported in ppm and J values in hertz. The elemental analyses were performed using a Leco CHNS-932 elemental analyzer

Insoluble methylene-bridged glycoluril dimers as sequestrants for dyes

• Suvenika Perera,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 2302–2314, doi:10.3762/bjoc.21.176

• locking or in deuterated dimethyl sulfoxide (DMSO-d6) or in deuterated chloroform (CDCl3). Melting points were measured on a Meltemp apparatus in open capillary tubes and are not corrected. IR spectra were recorded on a Thermo Nicolet NEXUS 670 FT/IR spectrometer by attenuated total reflectance (ATR) and

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• a final concentration of 0.5 mg/mL. Plates were incubated for 3 hours at 37 °C in a CO2 incubator to allow for formazan crystal formation. Subsequently, 150 μL of dimethyl sulfoxide (DMSO) was added to each well to solubilize the formazan. Plates were shaken for 15 minutes, and absorbance was

Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent Cyrene^TM under one-pot conditions

• Zoltán Medgyesi and
• László T. Mika

Beilstein J. Org. Chem. 2025, 21, 1544–1551, doi:10.3762/bjoc.21.117

• used for click reactions such as chlorinated hydrocarbons [15][16], toluene [16], tetrahydrofuran (THF) [17][18], N,N-dimethylformamide (DMF) [19][20], N-methylpyrrolidone (NMP) [21], dimethyl sulfoxide (DMSO) [17][19][22], or acetonitrile [23] are classified into Class 1 and 2, of which applications

• phenylacetylene, 2.5 mL solvent, 0.01 mmol CuI, 0.1 mmol Et3N, T = 30 °C, t = 4 h. DCM: dichloromethane, DMF: N,N-dimethylformamide, NMP: N-methylpyrrolidone, DMSO: dimethyl sulfoxide, 2Me-THF: 2-methyltetrahydrofuran, Me-4MeOV: methyl 4-methoxyvalerate, Et-4EtOV: ethyl 4-ethoxyvalerate, MeLev: methyl levulinate

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

• Betty A. Kustiana,
• Galuh Widiyarti and
• Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

• 350–352 in good yields via benzyne intermediate 353 followed by a [2 + 2] cycloaddition with the sulfoxide affording an o-quinone intermediate 354 (Scheme 78) [132]. Furthermore, dioxolane compounds have also been subjected to synthesize cinnamic acid derivatives through CO2 release. For example, Chen

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

• generated the [1 + 1] macrocycle 39 as the sole product. In contrast, polar aprotic solvents such as dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), or acetonitrile (MeCN) favored precipitation of the [2 + 2] macrocycle 40. Notably, the macrocycle 40 underwent spontaneous structural reorganization

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

• Exactive Orbitrap. General procedure A. 4-Fluorobenzaldehyde, the corresponding N-methylated amino alcohol and potassium carbonate were suspended in dimethyl sulfoxide and stirred for 30 hours at 120 °C. The resulting suspension was poured on crushed ice and extracted four times with chloroform, dried over

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

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

• devoted to dimethyl sulfoxide, dihalomethanes, hexamethylene tetramine, and glyoxylates as C1-building blocks, substituting formaldehyde. Review Methanol as a source of formaldehyde There are several reports on the use of alcohols under oxidative conditions as aldehyde surrogates in Ugi and Passerini

• , eventually, in other MCRs where formaldehyde acts as a C1 building block [16]. As can be seen in Scheme 3, under this strategy a wide variety of diamide compounds 1 could be afforded with very good yields applying MeOH as a formaldehyde source in a traditional Ugi reaction. Dimethyl sulfoxide (DMSO) as

• surrogate and source of formaldehyde Dimethyl sulfoxide is a well-known polar-aprotic solvent with high boiling point that is used in several organic synthetic reactions because of affordable cost and relatively low toxicity. There are numerous examples that show the use of DMSO as a C1 or C2 building block

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• (trifluoromethyl)benzene (1,4-C6H4(CF3)2, Central Glass Co., 99%); dimethyl sulfoxide (DMSO, Fisher Scientific, ACS grade); anhydrous magnesium sulfate (MgSO4, Fisher Scientific); Cu powder (Strem Chemicals, 99%); dichloromethane (EMD Chemicals, ACS grade); acetone (technical grade); THF (Aldrich/Merck, ACS grade

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

• microbroth single-dose assays. Dimethyl sulfoxide was used at a final concentration of 0.1% as negative control. Microbroth dilution assays [52] for the most potent bioactive compounds 7b and 7h were performed using nine serial dilutions of the tested compounds with final concentrations of 256, 128, 64, 32

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

• Radell Echemendía,
• Carlee A. Montgomery,
• Fabio Cuzzucoli,
• Antonio C. B. Burtoloso and
• Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

• those that lead to α-alkyl-substituted compounds, is still challenging [27]. For example, in the SN2 reaction of alkyl halides with sulfoxonium ylides, the initially formed α-alkyl-substituted ylide reacts further with the halide to expel the sulfoxide and ultimately generate an α-halogenated product

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• sulfoxide (DMSO) must be available as CD forms the inclusion complex), (5) the yield of the end-capping reaction must be high, (6) the end-capping reagent and rotaxane must dissolve in the same solvent to facilitate a homogeneous reaction, and (7) the rotaxane must be isolable from the reaction mixture. The

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

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

• inability of O2•– detection is not known at present. Upon addition of dimethyl sulfoxide (DMSO) to this system, an adduct of DEPMPO and •CH3 (DEPMPO-CH3), which was presumably generated from the reaction of •OH and DMSO, was clearly observed, further confirming the generation of •OH (Figure 5b(iii)). At the

• by blue LED lamp. (iii) catC60 5 µM, NADH 8 mM, DETAPAC 1 mM, and DEPMPO 100 mM in a 4-to-1 (v/v) mixture of PBS(–) and dimethyl sulfoxide (DMSO) under irradiation for 30 min by blue LED lamp. (iv) catC60 5 µM, PyBA 67 µM, NADH 8 mM, DETAPAC 1 mM, and DEPMPO 100 mM in a 4-to-1 (v/v) mixture of PBS

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

• anode to form a sulfoxide. Subsequent hydrogen atom abstraction by a chlorine radical leads to the formation of an intermediate carbon radical, whose resonant intermediate reacts with another chlorine radical to produce the desired α-chlorosulfoxide product (Scheme 14). 1.1.2 Unsaturated bond

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• , chlorinated species 1h and 1i, and carboxylic acid-containing 1s, developed high quality crystals from standing solutions in dimethyl sulfoxide for 1h and 1i, and methanol for 1s. Their molecular crystal structures were determined and are shown in Figure 1b displaying the classic cone conformation for both

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

• -azido-1-propanamine to give the desired AzidoTMT linker. Furthermore, Makarov et al. developed a linker containing a sulfoxide (SOX) group, which is well-known for specific fragmentation releasing the reporter ion at m/z 179.0849 (Figure 7C) [81][86][87]. The preparation of the tag is based on a five

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu₄NBF₄ or electrogenerated acid

• Mizuki Yamaguchi,
• Hiroki Shimao,
• Kengo Hamasaki,
• Keiji Nishiwaki,
• Shigenori Kashimura and
• Kouichi Matsumoto

Beilstein J. Org. Chem. 2024, 20, 2261–2269, doi:10.3762/bjoc.20.194

• , entry 6), but TfOH gave the product 2a in 72% yield (Table 1, entry 7). As for the solvent, CH3CN slightly afforded 2a, although N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) were not suitable for the reactions (Table 1, entries 8–10). A fluorine source, such as Bu4NF or BF3·Et2O, instead of

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

• dimethyl sulfoxide (DMSO), methanol (MeOH), methyl tert-butyl ether (MTBE), and n-hexane. Measurements in triplicates. 0.5–1% only for MC and CMC. PEG, MC, CMC: % % w/v. Other: % % v/v. Note: 2% PEG-8000 is present as a standard component in all reactions, unless otherwise stated. n.d.: not determined

• ), methylcellulose (MC), carboxymethylcellulose (CMC), choline chloride/urea (ChCl/urea), choline chloride/glycerol (ChCl/glycerol), and betaine/ethylene glycol (betaine/EG). The reference experiment is labeled as shaded bars. B) represents dimethyl sulfoxide (DMSO), methanol (MeOH), methyl tert-butyl ether (MTBE

From perfluoroalkyl aryl sulfoxides to ortho thioethers

• Yang Li,
• Guillaume Dagousset,
• Emmanuel Magnier and
• Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

• -pot two-step protocol. Several aryl-SCF3 compounds are reported by variation of the nitrile or of the trifluoroalkyl sulfoxide starting material. The variation of the perfluoroalkyl chain was also possible. Keywords: ortho functionalization; rearrangement; sulfoxide; Introduction Since decades

• Discussion We started our optimization with the reaction between acetonitrile and phenyl trifluoromethyl sulfoxide (1a, Table 1). We firstly chose the same stoichiometry as described in our previous study and tried to reduce the reaction time by the help of microwave heating (Table 1, entry 1). Under these

• decided to use 2 equivalents of DIPEA at low temperature. After ten minutes at −15 °C to allow for the reaction between phenyl trifluoromethyl sulfoxide (1a) and acetonitrile, the base was added and the reaction was stirred for the same amount of time. To our delight, a good NMR yield of 74% was received