Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers

• Kenichi Kato,
• Tatsuki Hiroi,
• Seina Okada,
• Shunsuke Ohtani and
• Tomoki Ogoshi

Beilstein J. Org. Chem. 2025, 21, 1183–1191, doi:10.3762/bjoc.21.95

• transition and decomposition. Then, gas adsorption properties [46][69][70][71][72] were evaluated after the samples were activated in vacuo at 120 °C (Figure 3 and Figures S801 and S802 in Supporting Information File 1). Their chemical structures did not necessarily contain branched or ladder-type

• , the methylene-alternating copolymers displayed gas adsorption properties. Further studies are underway towards novel functional materials containing fully π-fused propellanes as flexible 3D building blocks. Chemical structures of fully π-fused propellanes and their typical reaction patterns toward

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

• products [10] were detected by 1H NMR in any UV-active fractions following chromatographic separations. To the best of our knowledge, none of these triazolopyrazine compounds (2–15) have yet been reported [15]. Compounds 3–15 all had their chemical structures confirmed following detailed analysis of 1D/2D

• and conditions: (i) 3 equiv PEA, PhCH3, silica, rt, 6 h; (ii) 10 equiv PEA, rt, 6 h. Chemical structures, reagents and conditions used to synthesise the new aminated triazolopyrazines 2–15. Biological data for activity of triazolopyrazine analogues 1–15 against P. falciparum 3D7 and the non-cancerous

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

• Daniel Straub,
• Markus Gross,
• Mona E. Arnold,
• Julia Zolg and
• Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

• perchlorotriphenylmethyl (PTM) or tris(2,4,6-trichlorophenyl)methyl (TTM) radicals degrades to half of their intensity within just a few minutes, while for their corresponding di- and multiradicals no fluorescence data is reported at all (see Figure 1a for chemical structures) [5][6]. However, research on fluorescent

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

• coding of responses, list of data types associated with each article, and the resulting main dataset from assessment of 240 research papers are available in our supporting data package. As all research articles include results based on original (raw) data, and include previously unreported chemical

• structures, every article was assigned a response to the criteria defined in Find_1, Find_4, and Access_3. Then, all remaining variables in Table 2 were assessed only for those studies where primary data had been shared, as established by Access_3. Results Data types More than 95% of research articles report

Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation

• Zhihua Liu,
• Ya-Zhi Chen,
• Ji Wang,
• Qingling Nie,
• Wei Zhao and
• Biao Wu

Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68

• with 18-crown-6 and tripodal receptor (CCDC: 2411575) and (b) chemical structures for three types of intermolecular interactions with complexed Cs+. (c) IGM plot illustrating the attraction between complexed Cs+ and complexed phosphate. Color coding in the range of −0.5 < ρ sign(λ2) < 0.5 a.u. Atom

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

• RNA. Key is the functionalization of the original N-(2-hydroxyethyl) moiety into a reactive handle providing a mild electrophile (LG), such as, e.g., N-(3-bromopropyl) or N-(3-mesyloxypropyl) [11]. Pepper aptamer reacts with different HBC derivatives. Chemical structures of the HBC derivatives used

• with the highest reactivity, they are consistent with ref. [11] and serve as references in this work. Chemical structures of the HBC dye family [7]. Variations to HBC530 highlighted in red color. All dyes shown bind non-covalently to Pepper RNA, a fluorescent light-up aptamer. For one of them (HBC530

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

• ). Qualitative study of C1·guest recognition properties by 1H NMR spectroscopy Next, we decided to perform a qualitative investigation of the host–guest properties of C1 by 1H NMR spectroscopy. Figure 3 shows the chemical structures of a panel of guests that were studied and the complexation-induced changes in

• , 71.2, 69.5, 67.4, 52.5, 48.4, 35.0, 16.3, 15.4 ppm; ESIMS (m/z): 751.13 ([M − 2Na]2−), calcd for [C50H56N16Na2S4O28]2−, 751.1064. Chemical structures of CB[n] and selected acyclic CB[n]-type molecular containers M1 and M0. a) 1H NMR spectrum (600, D2O, rt) and b) 13C NMR spectrum recorded (150 MHz, D2O

• , rt) for C1. Chemical structures of guests used in this study along with the complexation induced changes in chemical shift (Δδ) upon formation of the C1·guest complexes. Negative Δδ values represent upfield shifts upon complexation. 1H NMR spectra recorded (400 MHz, D2O, rt) for: a) Me6PXDA (0.5 mM

Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

• Yuuki Ishii,
• Minoru Yamaji,
• Fumito Tani,
• Kenta Goto,
• Yoshihiro Kubozono and
• Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

• . In this study, octafluorinated phenacenes, F8-phenacenes F8PIC, F8FUL, and F87PHEN (see Figure 1 for their chemical structures), were systematically synthesized via the Mallory photoreaction [46] as the key step, and their UV–vis and fluorescence spectra were investigated in comparison with those of

• the manipulation of the solid-state optoelectronic nature of polycyclic aromatic molecules to develop future functional materials in organic electronics. Chemical structures of phenacenes studied in this work. UV–vis and fluorescence spectra of F8PIC (a), F8FUL (b), and F87PHEN (c) (red lines) and the

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• File 1; compounds 3a, 4b–d, 11, and 12). If insolubles were present after pH 1–2 was reached, the suspension was filtered. Purification is described in Supporting Information File 1 for the individual compounds 3a, 4b–d, 11, and 12. A) Chemical structures of hypermodified nucleobase queuine and

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• calculations were carried out on the same level of theory. A Boltzmann-averaged spectra were created and compared to the experimental spectrum using SpecDis 1.71 [12]. Chemical structures of compounds 1–6, prototenellin D and pretenellin B [7]. Key 1H-1H COSY, HMBC and ROESY correlations of 1. Comparison of

Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

• Abel Cárdenas,
• Zexin Jin,
• Yong Ni,
• Jishan Wu,
• Yan Xia,
• Francisco Javier Ramírez and
• Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

• were generated using the continuous set of gauge transformations (CSGT) method, as implemented in the Gaussian 09 suite, and the AICD 2.0.0 program [34]. Chemical structures of heptacene, diindenoanthracene (DIAn), and the molecules of 1 and 2 studied in this work (TIPS: triisopropylsilyl, Mes: mesityl

• oxidized radical cations (blue) and dications (red). ACID plots at the CSGT-B3LYP/6-311G(d,p) level for dicationic species m-12+ (top) and m-22+ (bottom). Supporting Information Supporting Information File 116: Chemical structures of m-1 and m-2, vibrational assignment of m-1, the 1730 cm−1 normal mode

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• ferric chloride (FeCl3) gave BPP-dione 4 in 70% yield. The chemical structures of BPP-OiPr 3 and BPP-dione 4 were characterized by 1H and 13C NMR spectroscopy as well as mass spectrometry (see Supporting Information File 1, Figures S8–S11). A single crystal of BPP-OiPr 3 suitable for X-ray diffraction

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• previous work [56][57], whereas compounds N4 and I1–I4 were synthesized according to Scheme 2 in the Experimental section. The chemical structures of all compounds were confirmed by 1H NMR and 13C NMR spectroscopy and high-resolution mass spectrometry. 1H NMR and 13C NMR spectra are shown in Supporting

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• supramolecular polymer in CHCl3/CH3CN (1:1, v/v, 298 K) at variable concentration. Variable-concentration 1H NMR spectra of the supramolecular polymer: (a) 2.0 mM, (b) 4.0 mM, (c) 6.0 mM, (d) 8.0 mM, and (e) 10 mM. a) Chemical structures of H-bonded macrocycles H1, H2, and guest G1, and schematic representation

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• , emission 590 nm). Chemical structures of ianthelliformisamines A–G (1–7) and aplysterol (8). Key COSY (), HMBC () and ROESY () correlations for ianthelliformisamines D (4) and E (5). Key COSY () and HMBC () correlations for ianthelliformisamines F (6) and G (7). Total synthesis of ianthelliformisamine D (4

Hypervalent iodine-mediated intramolecular alkene halocyclisation

• Charu Bansal,
• Oliver Ruggles,
• Albert C. Rowett and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

• Charu Bansal Oliver Ruggles Albert C. Rowett Alastair J. J. Lennox University of Bristol, School of Chemistry, Bristol, BS8 1TS, UK 10.3762/bjoc.20.258 Abstract The chemistry of hypervalent iodine (HVI) reagents has gathered increased attention towards the synthesis of a wide range of chemical

• structures. HVI reagents are characterized by their diverse reactivity as oxidants and electrophilic reagents. In addition, they are inexpensive, non-toxic and considered to be environmentally friendly. An important application of HVI reagents is the synthesis of halogenated cyclic compounds, in particular

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

Chemical structure metagenomics of microbial natural products: surveying nonribosomal peptides and beyond

• Thomas Ma and
• John Chu

Beilstein J. Org. Chem. 2024, 20, 3050–3060, doi:10.3762/bjoc.20.253

• vocabulary for this molecular language, and knowing their chemical structures is key to understanding this form of information exchange [38]. It is worth pointing out that chemical structure, but not bioactivity, is the unique descriptor of a molecule. Molecules with the same chemical structures are (by

• corresponding nucleic acid sequence. Proteinaceous enzymes then go on to catalyze biosynthetic reactions that put together small molecule building blocks (BB) to generate natural products with extremely diverse chemical structures. Because the intricacy of this process is not fully understood, scientists still

• underexplored by two-fold a particular BB (or a group of BBs with similar chemical structures), respectively (Figure 3c). Phenylglycine and its derivatives (the sp2 group of BBs, Figure 3d) turned out to be the most oversampled group of BBs. This group of BBs included noncanonical amino acids characteristic of

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

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• , 134.5, 133.2, 131.1, 129.5, 128.6, 128.3, 127.8, 127.5, 127.2, 123.7, 123.2, 122.8, 117.3, 113.6, 69.8, 63.2, 32.9, 32.0, 29.9, 29.7, 29.5, 29.4, 26.2, 25.8, 22.8, 14.2; ASAP–HRMS (m/z): [M + H]+ calcd for C64H65N4O2, 921.5107; found, 921.5108. Chemical structures of violanthrone and

• dihydroxyviolanthrone. Chemical structures of 2b and 3b. Optimised ground state geometries of compounds 2 and 3 calculated using B3LYP/6-311G(d,p) in the gas phase. Views of the crystal structure of 3b (left, shows displacement ellipsoids drawn at 50% probability level, right showing the twisted conformation

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

• present study for controlling both the location and photodynamic actions of a cationic derivative of C60 (catC60), a simple model compound of the triad molecules, in a membrane via π–π interactions with 1-pyrenebutyric acid (PyBA). (d–f) Chemical structures of 1,2-dimyristoyl-sn-glycero-3-phosphocholine

Young investigators in natural products chemistry, biosynthesis, and enzymology

• Jeffrey D. Rudolf,
• Lena Barra and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 2720–2721, doi:10.3762/bjoc.20.229

• clusters, and enzymes, development of chemical probes, biocatalysis and chemoenzymatic total synthesis, enzymatic mechanisms, and computational investigations of chemical structures and reactions. All of the major classes of natural products are represented here: nonribosomal peptides, ribosomally

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

• Connor R. M. MacDonald and
• Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

• Stefan P. Schmid,
• Leon Schlosser,
• Frank Glorius and
• Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

• , the interest to describe the influence of substrate or catalyst structures on the rate or selectivity of a reaction is well-established and led among others to the introduction of Hammett parameters to relate chemical structures to both kinetic and thermodynamic reaction properties [28] (Figure 4). As

Finding the most potent compounds using active learning on molecular pairs

• Zachary Fralish and
• Daniel Reker

Beilstein J. Org. Chem. 2024, 20, 2152–2162, doi:10.3762/bjoc.20.185

• properties (‘exploitative’) [18], or a combination of both (‘balanced’) [8]. Explorative active learning provides diverse chemical structures to support model learning while exploitative approaches instead bias towards rapid identification of favorable compounds. As such, explorative strategies may not

• transformation of chemical space. The deep models using this approach also more accurately identified hits in external test sets generated through simulated temporal splits, indicating the ActiveDelta approach’s applicability and generalizability to novel chemical structures that would likely be encountered