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

• . Photophysical studies indicated a fluorescence mechanism via intramolecular charge transfer (ICT). Results and Discussion Synthesis of 5-arylidene derivatives under microwave heating To find the ideal reaction conditions for the synthesis of 5-arylidene derivatives, benzaldehyde (1a) and rhodanine (2a) were

Visible-light-driven NHC and organophotoredox dual catalysis for the synthesis of carbonyl compounds

• Vasudevan Dhayalan

Beilstein J. Org. Chem. 2025, 21, 2584–2603, doi:10.3762/bjoc.21.200

• radical-/radical cross-coupling performed between intermediates C and E. The reaction of acyl fluoride 4 in the presence of Cs2CO3 and NHC to produce benzoate A and the formation of some reactive intermediates are shown in Scheme 2. These methods will find suitable application in medicinal chemistry and

• used for late-stage modification of bioactive compounds, including natural products. These developments will find suitable applications in medicinal chemistry for introducible organosilyl groups (Scheme 5) [55]. A visible-light-induced Friedel–Crafts acylation of arenes and heteroarenes was reported by

Isoorotamide-based peptide nucleic acid nucleobases with extended linkers aimed at distal base recognition of adenosine in double helical RNA

• Grant D. Walby,
• Brandon R. Tessier,
• Tristan L. Mabee,
• Jennah M. Hoke,
• Hallie M. Bleam,
• Angelina Giglio-Tos,
• Emily E. Harding,
• Vladislavs Baskevics,
• Martins Katkevics,
• Eriks Rozners and
• James A. MacKay

Beilstein J. Org. Chem. 2025, 21, 2513–2523, doi:10.3762/bjoc.21.193

• functionalized. We noted that isoorotic acid offered an opportune core from which to prepare extended nucleobase monomers through amide bond formation (Figure 3a) [34]. Secondly, the work began with the initial goal to find an extended nucleobase scaffold capable of strong binding to A and then reverse its point

Synthesis of the tetracyclic skeleton of Aspidosperma alkaloids via PET-initiated cationic radical-derived interrupted [2 + 2]/retro-Mannich reaction

• Ru-Dong Liu,
• Jian-Yu Long,
• Zhi-Lin Song,
• Zhen Yang and
• Zhong-Chao Zhang

Beilstein J. Org. Chem. 2025, 21, 2470–2478, doi:10.3762/bjoc.21.189

• TS2, the reactant (IN2), and the C19–C3 bond cleavage product IN3 wells (Figure 2c). Possible intermediates with a bicyclo[2.2.0]hexane unit located on the PES minimum were investigated by performing two-dimensional scans of simplified structures to find a minimum. When the nonbonding sp3 orbital of

The intramolecular stabilizing effects of O-benzoyl substituents as a driving force of the acid-promoted pyranoside-into-furanoside rearrangement

• Alexey G. Gerbst,
• Sofya P. Nikogosova,
• Darya A. Rastrepaeva,
• Dmitry A. Argunov,
• Vadim B. Krylov and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2025, 21, 2456–2464, doi:10.3762/bjoc.21.187

• given in Table 1. Looking at the obtained conformations (Figure 5B), one can find that the same π–π interactions are present in the α-galactoside structures as in their β-isomers. However, there is a possibility of another interaction. This is the repulsion between the cis-oriented O-1 and O-2 atoms in

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

• along with comparator H2 as solid-state sequestrants for a panel of five dyes (methylene blue, methylene violet, acridine orange, rhodamine 6G, and methyl violet 6B). We find that catechol-walled H2 (OH substituents) is a superior sequestrant compared to G2W1–G2W4 (OMe substituents). X-ray crystal

Halogenated butyrolactones from the biomass-derived synthon levoglucosenone

• Johannes Puschnig,
• Martyn Jevric and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2025, 21, 2297–2301, doi:10.3762/bjoc.21.175

• sofosbuvir (2). Fluorination at C2 in the nucleoside results in metabolic stability and resistance to hydrolysis as it destabilizes the formation of a C1 oxocarbenium ion [5][6]. Trifluoromethylated γ-butyrolactones also find applications as antiviral agents, for example, lactone 4 which has activity against

Research towards selective inhibition of the CLK3 kinase

• Vinay Kumar Singh,
• Frédéric Justaud,
• Dabbugoddu Brahmaiah,
• Nangunoori Sampath Kumar,
• Blandine Baratte,
• Thomas Robert,
• Stéphane Bach,
• Chada Raji Reddy,
• Nicolas Levoin and
• René L. Grée

Beilstein J. Org. Chem. 2025, 21, 2250–2259, doi:10.3762/bjoc.21.172

• . However, these derivatives remain still less potent on CLK3 than on the other CLKs. Therefore, they cannot be qualified as bona fide chemical probes for this CLK3 kinase. Structural and biochemical studies have been undertaken to find more selective CLKs inhibitors. Particularly, a detailed study has

Pd-catalyzed dehydrogenative arylation of arylhydrazines to access non-symmetric azobenzenes, including tetra-ortho derivatives

• Loris Geminiani,
• Kathrin Junge,
• Matthias Beller and
• Jean-François Soulé

Beilstein J. Org. Chem. 2025, 21, 2234–2242, doi:10.3762/bjoc.21.170

• (allyl)]2, XPhos, t-BuONa in 1,2-dimethoxyethane (DME)) [55]. The reaction outcomes were analyzed with both GC/MS and GC/FID analysis. Under these conditions, we were pleased to find that 1-phenyl-2-(o-tolyl)diazene (3a) was obtained with a GC yield of 50% (Table 1, entry 1). While all starting materials

Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions

• Ivan Keng Wee On,
• Yu Kun Choo,
• Sambhav Baid and
• Ye Zhu

Beilstein J. Org. Chem. 2025, 21, 1995–2006, doi:10.3762/bjoc.21.155

• are excluded. In other words, the number set of atoms will be reduced by one. c) Consider "dummy" atoms from multiple bonds as lower priority than real atoms of the same type. Step 3: Determination of stereocontrol pathways. For each set of atoms identified in step 2: 3.1 Find the shortest path

Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines

• Margherita Gazzotti,
• Fabrizio Medici,
• Valerio Chiroli,
• Laura Raimondi,
• Sergio Rossi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147

• chiral diimines of aromatic aldehydes with trans-1,2-diaminocyclohexane was initially investigated under traditional batch conditions through a series of screening experiments designed to find the optimal reaction conditions. Diimine 1a was selected as model substrate for the intramolecular coupling

Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

• photophysical properties of this photoswitch class. The vast possibility of combinations and the straightforward syntheses make these compounds extremely attractive, however, somewhat difficult to strictly categorise: among the azoheteroarenes we find mainly nitrogen-based heterocycles such as pyrazole, pyrrole

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

• Somayyeh Kheirjou,
• Jan Riebe,
• Maike Thiele,
• Christoph Wölper and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2025, 21, 1719–1729, doi:10.3762/bjoc.21.134

• single precursor, but this is unnecessary if only macrocyclic bis-BINOL derivatives are desired. For this reason, we sought to find optimized syntheses for such BINOL-based macrocycles (see Figure 2). After investigating different synthetic routes (vide infra), we found that Williamson-type ether

• macrocycles. In the Williamson approach, we find increasing yields in the series H-M15/6/7/8 and iPr-M15/6/7/8, with the best yield obtained for the longest octaethylene glycol linkers in H/iPr-M18. To our surprise, the Me-series not only gives generally better yields, but also shows the maximum yield for the

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• dramatically, and the number of nitrogen-containing compounds continuously increased. These compounds find broad applications in synthesizing energetic materials, dyes, flavorings and fragrances, pharmaceutical and pesticide intermediates, as well as specialty chemicals [2]. As delineated in Figure 1, a

3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles

• Julia I. Pavlenko,
• Pavel A. Sakharov,
• Anastasiya V. Agafonova,
• Derenik A. Isadzhanyan,
• Alexander F. Khlebnikov and
• Mikhail S. Novikov

Beilstein J. Org. Chem. 2025, 21, 1595–1602, doi:10.3762/bjoc.21.123

• . Heating of indole 9a with azirine 2a in the presence of 5 mol % of Ni(hfacac)2 afforded the desired annulation product 10 in 41% yield (Scheme 5). Unfortunately, we were unable to find conditions that allowed a similar reaction of NH-indole 9b to occur. At the same time, when Ni(hfacac)2 was replaced with

Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds

• Lidia Zaharieva,
• Vera Deneva,
• Fadhil S. Kamounah,
• Nikolay Vassilev,
• Ivan Angelov,
• Michael Pittelkow and
• Liudmil Antonov

Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105

• (problem with possibility to achieve a clean on-state of switching). All this means that structural changes are needed in order to find an azo compound, based on 7-hydroxyquinoline, where the individual tautomers have energies ranked in the following way: EE<

N-Salicyl-amino acid derivatives with antiparasitic activity from Pseudomonas sp. UIAU-6B

• Joy E. Rajakulendran,
• Emmanuel Tope Oluwabusola,
• Michela Cerone,
• Terry K. Smith,
• Olusoji O. Adebisi,
• Adefolalu Adedotun,
• Gagan Preet,
• Sylvia Soldatou,
• Hai Deng,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103

• Biochemistry, Federal University of Lafia, Nigeria 10.3762/bjoc.21.103 Abstract Pseudomonads strains represent a promising source of bioactive compounds with potential pharmaceutical applications. The necessity to find new drugs is underscored by the increased concern over antimicrobial resistance in the

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

• Julius Seumer,
• Nicolai Ree and
• Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

• Tomberg et al. [9] more accessible, we implemented a simple program that given a SMILES string goes through all of the SMARTS patterns to find matches, sorts the matches, and returns a visual output of the result. The algorithm sequentially sorts according to the number of heavy atom matches, the sum of

Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold

• Henry S. T. Smith,
• Ben Giuliani,
• Kanchana Wijesekera,
• Kah Yean Lum,
• Sandra Duffy,
• Aaron Lock,
• Jonathan M. White,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90

• (MMV) [3]. OSM’s aim is to “find a drug for malaria as quickly as possible” [3]. In the past, OSM synthesised and screened various derivatives of three related parent scaffolds (series 1–3) provided by GlaxoSmithKline (GSK) in non-commercial antimalarial screening datasets [4]. The group’s current

Gold extraction at the molecular level using α- and β-cyclodextrins

• Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

• processes with high energetic costs such as heating or applying high pressure. Seeking to find an eco-friendlier method to strip the gold from carbon, the Stoddart group investigated the use of α-CD in a series of tests at the laboratory scale in which suspensions of KAu(CN)2-loaded carbon (50 mg

Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

• Shyam Sathyamoorthi,
• Appasaheb K. Nirpal,
• Dnyaneshwar A. Gorve and
• Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

• carbamate substrate 15 and N-hydroxy carbamate substrate 16. As we had successfully installed tosyloxy and mesyloxy groups, we wondered if other sulfonic acids would be compatible with our reaction conditions (Table 3). We were pleased to find that the amino-sulfonoxylation reaction proceeded with a diverse

• compatible with our optimized protocols (Table 4). Earlier in the project, we had focused exclusively on substrates derived from trans-homo-allylic alcohols. We were thus pleased to find that a substrate synthesized from cis-3-hexen-1-ol was equally compatible and gave product in an excellent yield and

• expect this metal-free protocol for alkene amino-oxygenation to find widespread use in both academic and industrial synthetic chemistry. Poor performers. Existing reports of intramolecular alkene functionalization reactions with nitreniums have focused on amino-trifluoroacetoxylations. We show the first

Data accessibility in the chemical sciences: an analysis of recent practice in organic chemistry journals

• Sally Bloodworth,
• Cerys Willoughby and
• Simon J. Coles

Beilstein J. Org. Chem. 2025, 21, 864–876, doi:10.3762/bjoc.21.70

• NMR data by some journals supports author compliance. We find that, although authors meet mandated requirements, there is very limited compliance with data sharing policies that are only recommended by journals. Overall, there is little evidence to suggest that authors’ publishing practice meets FAIR

• research but as a driver for discovery. Data sharing enables researchers to find and repurpose data without the costs of repeated data collection, and secondary analysis of existing data can lead to new findings and broad impact [1][2][3]. Many examples of advanced practice and policy for data sharing

• non-machine-readable PDF format. Only 1% of studies shared unprocessed NMR data; despite >93% of research articles reporting NMR data as a main output of their work, and the existence of strongly worded recommendations for NMR data-sharing in the author guidelines of 5/12 journals. We find that, for

Substituent effects in N-acetylated phenylazopyrazole photoswitches

• Radek Tovtik,
• Dennis Marzin,
• Pia Weigel,
• Stefano Crespi and
• Nadja A. Simeth

Beilstein J. Org. Chem. 2025, 21, 830–838, doi:10.3762/bjoc.21.66

• found. We thus suspect that the substituents play a crucial role in in the population of the respective exited state and we can at this state not rule out a contribution also from the triplet state. Moreover, we could not find a quantitative correlation between the R-substituents and ΦE→Z, however, some

Recent advances in the electrochemical synthesis of organophosphorus compounds

• Babak Kaboudin,
• Milad Behroozi,
• Sepideh Sadighi and
• Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

• as the cathode and changed the anode electrode to find the best efficiency. The platinum plate electrode is more suitable than felt due to its larger contact surface, and using graphite electrodes in the form of a rod had good efficiency. The best results were obtained using a RVC electrode as the

• functional groups and can help to find new drug candidates. The reaction was carried out in an undivided cell where the anode was platinum, and the cathode was graphite at a constant current of 5 mA. The mechanistic study showed that a radical process might be involved in the reaction, and the role of

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

• Christian Akakpo,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

• according to the results of 1H NMR dilution experiments. The molecular recognition behavior of the hosts C1 and M1 toward a panel of seven ammonium ions was explored by 1H NMR spectroscopy and isothermal titration calorimetry (ITC). We find that C1 generally binds slightly more tightly than M1 toward a

• out the effect of chain length by a comparison of Me6PDA with Me6HDA. We find that the longer and more hydrophobic Me6HDA guest binds 1.92-fold stronger to C1; similarly, Me6HDA binds 2.25-fold stronger to M1. These differences are likely due to the increased hydrophobicity of the additional CH2 group

• . Finally, we can compare the binding of the primary ammonium versus the corresponding quaternary ammonium ion guest toward C1 and separately M1. We find that C1 binds the quaternary ammoniums somewhat stronger: Me6PXDA vs PXDA (1.72-fold), Me6CHDA vs CHDA (2.42-fold), Me3AdA vs AdA (4.59-fold). A similar