Kinetic resolution of racemic planar-chiral vinylcymantrenes by molybdenum-catalyzed asymmetric metathesis dimerization

• Haruna Imazu,
• Hitoshi Izu,
• Yasuhiro Ohki and
• Masamichi Ogasawara

Beilstein J. Org. Chem. 2026, 22, 568–574, doi:10.3762/bjoc.22.42

• ], reveals that the molybdenum-catalyzed asymmetric metathesis reactions are powerful tools to control planar chirality in various transition-metal complexes. ORTEP drawing of the X-ray structure of (S,S)-(–)-2b with atom numbering (thermal ellipsoids set at the 30% probability level). Selected bond lengths

Synthesis and stereochemical analysis of dynamic planar chiral oxa[7]orthocyclophene

• Yukiho Hashimoto,
• Yuuya Kawasaki,
• Kazunobu Igawa and
• Katsuhiko Tomooka

Beilstein J. Org. Chem. 2026, 22, 436–442, doi:10.3762/bjoc.22.30

• potential for iodine. Retrosynthesis of oxacyclophene 1ad. Synthesis of C6-iodo-substituted oxacyclophene 1ad. Synthesis of derivatives 1ab and 1ac, and ORTEP drawing of 1ac (ellipsoid set at 50% probability level). Epoxidation of (S)-1ab. Supporting Information Supporting Information File 25: Experimental

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

• % probability, b) and c) show Se···Se and Se···C intermolecular interaction in compound. DFT optimised structure of compounds a) 7 and b) 8. HOMO, LUMO, and the energy gap of the compounds: a) 7 and b) 8. Mulliken atomic charge of the compounds: a) 7 and b) 8. MEP analysis of the compounds: a) 7 and b) 8. log

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

• . Molecular structures of partially nitrated calixarene 16 (a) and exhaustively nitrated calixarene 15 (b). Two projections shown in each case and thermal ellipsoids are drawn at a 50% probability level. Planar and energy-minimized structures (with CHCl3 molecule included and triazole groups highlighted) of

Design, synthesis and biological evaluation of 2,5-diaryloxazolo[4,5-d]pyrimidin-7-ylamines as selective cytotoxic agents against HeLa cells

• Maryna V. Kachaeva,
• Agnieszka B. Olejniczak,
• Marta Denel-Bobrowska,
• Victor V. Zhirnov,
• Yevheniia S. Velihina,
• Stepan G. Pilyo and
• Volodymyr S. Brovarets

Beilstein J. Org. Chem. 2026, 22, 390–398, doi:10.3762/bjoc.22.27

• mechanisms of action have utilitarian value, as they do not account for the probability of including targets not inherent to existing drugs in their molecular mechanisms of anticancer action. The physicochemical properties of such compounds may not fit the parameters developed from databases of approved

• probabilistic nature of the evaluation, parameters for which the probability of a compound's relevant property is predicted to occur in the range 0.3 < p < 0.7 does not allow a confident conclusion to be drawn and require further evaluation [21]. The same applies to the conflicting results obtained by different

• (Table 3). With regard to the substrate specificity of Pgp, it is highly probable that these compounds are not substrates of this protein, although compounds 1 and 7, unlike 9, appear to be capable of inhibiting it (Table 3). A low probability of oxidative metabolism of these compounds by the studied

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

• , Et3N, 4 Å molecular sieves, EtOH, rt, 1.5 h, then NaBH4, 0 °C to rt, 1.2 h, then HCl, 74%. a) Single-crystal X-ray structure of 1·HCl. Displacement ellipsoids of the nonhydrogen atoms are shown at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary size. Nitrogen atoms are blue

Competitive cyclization of ethyl trifluoroacetoacetate and methyl ketones with 1,3-diamino-2-propanol into hydrogenated oxazolo- and pyrimido-condensed pyridones

• Svetlana O. Kushch,
• Marina V. Goryaeva,
• Yanina V. Burgart,
• Marina A. Ezhikova,
• Mikhail I. Kodess,
• Pavel A. Slepukhin,
• Alexandrina S. Volobueva,
• Vladimir V. Zarubaev and
• Victor I. Saloutin

Beilstein J. Org. Chem. 2025, 21, 2716–2729, doi:10.3762/bjoc.21.209

• : 2479556), and 4dct (e, CCDC: 2479557) showing with the thermal ellipsoids at 50% probability. ORTEP view of compound 5ctc (a, CCDC: 2479558), 5ctt (b, CCDC: 2479559) showing with the thermal ellipsoids at 50% probability. The fragments of the 1H NMR spectra (400 MHz, DMSO-d6) of diastereomers 4acc (a

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

• : a) 1H NMR spectra (600 MHz, DMSO-d6) with expansions, and b) 13C NMR spectra (151 MHz, DMSO-d6) with expansions. a) Molecular structure of 3n with crystallographic labeling (50% probability displacement). b) Perspective views of intermolecular hydrogen bonds (dotted lines) of 3n. (‘) symmetry

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

• with the highest probability. The snapshots in Figure 7 reveal problems with the Db bases in the binding pocket. As discussed earlier, each Db base has a linker containing an NH moiety aimed at forming a stabilizing hydrogen bond with the carbonyl from the linker of the adjacent PNA M-base. Such a

Bioinspired total syntheses of natural products: a personal adventure

• Zhengyi Qin,
• Yuting Yang,
• Nuran Yan,
• Xinyu Liang,
• Zhiyu Zhang,
• Yaxuan Duan,
• Huilin Li and
• Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

• process, which further supported the probability of the proposed biosynthetic approach. Subsequently, site-selective methylation on phenol provided 24, which further underwent O-directed demethylation to afford (12S)-hydroxymonocerin. On the other hand, a two-step protocol involving Mitsunobu reaction

Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid

• Yana I. Sakhno,
• Oleksander V. Buravov,
• Kostyantyn Yu. Yurkov,
• Anastasia Yu. Andryushchenko,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2030–2035, doi:10.3762/bjoc.21.158

• are shown at 50% probability level. Diversity of heterocyclization products from reaction of aminoazoles with salicylaldehydes, and pyruvic acids. MCRs of 3-amino-5-methylthio-1,2,4-triazole (1a) and 3-amino-5-methoxy-1,2,4-triazole (1b) with salicylaldehydes 2a–f, and pyruvic acid (3). MCRs of 3

[3 + 2] Cycloaddition of thioformylium methylide with various arylidene-azolones in the synthesis of 7-thia-3-azaspiro[4.4]nonan-4-ones

• Daniil I. Rudik,
• Irina V. Tiushina,
• Anatoly I. Sokolov,
• Alexander Yu. Smirnov,
• Alexander R. Romanenko,
• Alexander A. Korlyukov,
• Andrey A. Mikhaylov and
• Mikhail S. Baranov

Beilstein J. Org. Chem. 2025, 21, 1791–1798, doi:10.3762/bjoc.21.141

• would be of help in further drug design of spirocyclic scaffolds. Single crystal X-ray analysis for the compounds 6e (A), 7d (B), 8e (C) and 9e (D). Atoms are shown as thermal ellipsoids at 50% probability. All hydrogen atoms, except the one at the stereogenic center, are omitted for clarity. Synthetic

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

• bistosylates 85/6/7/8 (1.0 equiv), Cs2CO3 (2.0 equiv), CH3CN, 80 °C. Molecular structure of macrocycle (R)-Me-M16 in the solid state (hydrogen atoms are omitted for clarity and thermal ellipsoids are set at the 60% probability level). The ethylene glycol chain is partially disordered, only one component is

Synthesis of an aza[5]helicene-incorporated macrocyclic heteroarene via oxidation of an o-phenylene-pyrrole-thiophene icosamer

• Yusuke Matsuo,
• Aoi Nakagawa,
• Shu Seki and
• Takayuki Tanaka

Beilstein J. Org. Chem. 2025, 21, 1561–1567, doi:10.3762/bjoc.21.119

• and nanobelt. (b) Cyclo[4]helicenylene and cyclo(oxa[5]helicenylene-biphenylene). (c) Intramolecular oxidative coupling of cyclic o-phenylene-pyrrole-thiophene dodecamers. X-ray crystal structure of 4. Thermal ellipsoids are scaled to 50% probability level. Solvent molecules and hydrogen atoms except

• for NHs are omitted for clarity. 1H NMR spectra of 5 in DMSO-d6 (a) at room temperature and (b) at 100 °C. (a) X-ray crystal structure of 5; (left) top view, (right) side view. Thermal ellipsoids are scaled to 50% probability level. Solvent molecules and hydrogen atoms except for NHs are omitted for

Highly distinguishable isomeric states of a tripodal arylazopyrazole derivative on graphite through electron/hole-induced switching at ambient conditions

• Himani Malik,
• Sudha Devi,
• Debapriya Gupta,
• Ankit Kumar Gaur,
• Sugumar Venkataramani and
• Thiruvancheril G. Gopakumar

Beilstein J. Org. Chem. 2025, 21, 1496–1507, doi:10.3762/bjoc.21.112

• tunneling current passing through the molecule at the tunneling junction. The electron/hole-induced switching reveals that the electron injection yields a higher switching probability than that through hole injection. It is also observed that the overall switching probability of FNAAP on the surface is

• the number of I–V measurements used for the analysis. Thus, the ratio of the number of switching events to the number of I–V used directly corresponds to the switching probability. The following observations are noted from the statistical analysis. 1) a threshold voltage is observed for the

• isomerization of the molecules at both positive and negative sample voltages (marked by red/blue arrow heads); 2) the switching probability increases exponentially with increasing voltage; 3) the switching probability at positive voltage is almost double than that at negative sample voltage; 4) a strong

Wittig reaction of cyclobisbiphenylenecarbonyl

• Taito Moribe,
• Junichiro Hirano,
• Hideaki Takano,
• Hiroshi Shinokubo and
• Norihito Fukui

Beilstein J. Org. Chem. 2025, 21, 1454–1461, doi:10.3762/bjoc.21.107

• beneficial for the development of advanced materials. Synthesis and structures of CBBC 1. X-ray crystal structures of (a) 3, (b) 4, and (c) 5 with thermal ellipsoids at 50% probability; all hydrogen atoms are omitted for clarity. VT 1H NMR spectra of 5 in CD2Cl2 at (a) 298 K, (b) 243 K, and (c) 203 K. Blue

Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles

• Vladimir G. Ilkin,
• Pavel S. Silaichev,
• Valeriy O. Filimonov,
• Tetyana V. Beryozkina,
• Margarita D. Likhacheva,
• Pavel A. Slepukhin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104

• from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk). Representatives of biologically active 1,2-thiazoles. Compound 3aa in thermal ellipsoids 50% probability. Synthesis of 2,5-dihydro-1,2-thiazoles. Synthesis of 2,3-dihydro-N-sulfonyl-1,2-thiazoles

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

• Krishna Pandey,
• Lucas X. Orton,
• Grayson Venus,
• Waseem A. Hussain,
• Toby Woods,
• Lichang Wang and
• Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

• CDCl3 and (CD3)2CO 1:2. Crystal structures of HIM 1 and LiBArF20 (A) and NaBArF24 (B). BARF cation is omitted for clarity. Nitrogen, oxygen, iodine, and metal (lithium or sodium) atoms are denoted by light blue, red, purple, and lavender color, respectively. Thermal ellipsoids drawn at 50% probability

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Luc Van Meervelt,
• Do Thi Thao and
• Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

• ellipsoids at the 30% probability level. The intramolecular hydrogen bond is shown as red dashed line. The bioavailability radar of studied compounds 5a–e. The interactions of potential drugs 5a–c in the active site of enzyme iNOS. The interactions of potential drugs 5d and 5e and control drug (DEX) in the

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

• acetylcholine-type unit (Me3NCH2CH2O(C=O)R) range from 3.5 Å to 5 Å with a maximum probability of 4.4 Å [74]. Figure 6 shows Me3N+···O=C contacts that are less than 4.40 Å. The large number of contacts that are significantly shorter than 4.40 Å establishes that Me3N+···O=C cation–dipole interactions play an

Cryptophycin unit B analogues

• Thomas Schachtsiek,
• Jona Voss,
• Maren Hamsen,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40

• % probability. Synthesis of modified unit B derivatives. a) HNO3, H2SO4, 0 °C, 5 h, 48% (isolated as monohydrate); b) SOCl2, MeOH, 0 °C, 90 min, then reflux, 17 h, 95%; c) Boc2O, NEt3, MeCN, H2O, rt, 22 h, 88%; d) H2, Pd/C, MeOH, rt, 25 h, 98%; e) either: formalin, NaBH3CN, HOAc, MeOH, rt, 20 min, 37%, or

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

• emission (anaerobic, dashed line) spectra in cyclohexane. Top: X-ray structure of 9,10-ANTH(BnF)2, thermal ellipsoids 50% probability. Bottom: a view down the crystallographic c-axis (left) and an off-side view (right) of the solid-state packing in the X-ray structure of 9,10-ANTH(BnF)2. Two different

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

• Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

• catalysis, rather than the more rigidly preorganized functionality required for transition-state binding. If it is easier for a cage to flex [146] or disassemble than to withstand the strain of a transition barrier, the entropic probability of effective transition-state binding is reduced (one can imagine

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• protection: The pivaloyl (OPiv) ester is another such participating ester protection with decreased migratory properties. Moreover, the intrinsic neopentyl property of the ester significantly reduces the probability of nucleophilic attack at the oxocarbenium centre instead of the anomeric carbon, thereby

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

• BPP-OiPr 3: a) top view, b) side view (thermal ellipsoids shown at 50% probability), and c) molecular packing of 3 in a unit cell. All the hydrogen atoms are omitted for clarity. a) UV–vis absorption spectra of BPP 2, BPP-OiPr 3, and BPP-dione 4 measured in toluene. Inset: magnified spectra of 2 and 3