Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles

• Constantine V. Milyutin,
• Andrey N. Komogortsev and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44

• Supporting Information File 2: General information, characterization data, NMR spectra and crystallographic data of synthesized compounds. Acknowledgements Crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic Chemistry, Moscow.

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• : Experimental procedures, characterization data, NMR spectra, and HPLC chromatograms. Funding This research was funded by an IAAR Research Support Program (Chiba Halogen Science: Halogen-Linkage of Molecular Functions); Chiba University Open Recruitment for International Exchange Program, Chiba University

Vinylogous functionalization of 4-alkylidene-5-aminopyrazoles with methyl trifluoropyruvates

• Judit Hostalet-Romero,
• Laura Carceller-Ferrer,
• Gonzalo Blay,
• Amparo Sanz-Marco,
• José R. Pedro and
• Carlos Vila

Beilstein J. Org. Chem. 2025, 21, 533–540, doi:10.3762/bjoc.21.41

• chromatography. Diastereoisomeric ratio (dr) determined by 1H NMR of the crude reaction mixture. Plausible mechanism and X-ray structure of compound 5aca. Optimization of the reaction conditions.a Supporting Information Supporting Information File 14: Detailed experimental procedures, characterization data, and

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

• a relatively fast and efficient conversion into the desired products. Further optimization of this promising photochemical method is currently under way in our laboratory. Isolation and characterization Pure samples of 9,10-ANTH(BnF)2 and 9-ANTH(BnF) were isolated by HPLC (Figure S3, Supporting

• removed in vacuo. Yield (NMR): 9-Br-10-BnF-ANTH (22%), 9,10-(BnF)2-ANTH (45%). Product characterization and NMR spectra 9-ANTH(BnF): white/yellow solid; isolated yield 14% based on ANTH; mp 177–179 °C; 19F NMR (CDCl3, δ/ppm): −73.61 (t, J = 17.7 Hz, 2F), −140.94 (m, 2F), −152.56 (t, J = 20.4 Hz, 1F

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• [17]. As a starting point for further derivatization, the synthesis and characterization of monohalogenated N-acetyl diazocines 2 and 3 (Figure 1) have been performed [22]. Unfortunately, diazocines in general, and N-acetyl diazocines in particular cannot be derivatized by electrophilic aromatic

• diazocine 23 in yields of 61% from bromide 2 and 81% from iodide 3 (Scheme 3). Nitriles are a good starting point for further functional group interconversions [39]. Photochemical characterization With these new N-acetyl diazocine derivatives at hand we turned towards the photochemical characterization, in

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• resolution of pure diastereomer anti-1. Supporting Information Supporting Information File 10: Characterization data, copies of spectra and HPLC chromatograms. Funding J.G.-P. thanks to the Universidad de Valladolid for a predoctoral fellowship. The Spanish MINECO (Project CTQ2014-59870 P) and the Junta de

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

• , although the synthesis and characterization (particularly crystallization) of low-symmetry structures remains challenging [227][231][232]. Likewise, COFs hosting chiral organocatalysts are known (Figure 6B) [226][233]. Frameworks are well-suited to hosting opposing reactive functionalities (e.g., acids and

• purify the cage by size-exclusion (GPC) due to the cage robustness [41]. Use of bulky internal groups can statistically bias cage self-assembly of mixed groups, a strategy previously reported [375]. Versatile characterization in the solid and solution states: The stable and soluble nature of covalent

Identification and removal of a cryptic impurity in pomalidomide-PEG based PROTAC

• Bingnan Wang,
• Yong Lu and
• Chuo Chen

Beilstein J. Org. Chem. 2025, 21, 407–411, doi:10.3762/bjoc.21.28

• the PEG chain on the relative retention time of 8 and 9 on HPLC. Supporting Information Supporting Information File 18: Computational details, general experimental information, synthetic procedures, compound characterization data, and copies of NMR spectra. Funding This work is supported by the NIH

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• CH3CN.a Supporting Information Supporting Information File 11: Experimental procedures and characterization data for all novel compounds 7a, 7b, 8a and 8b. Supporting Information File 12: 1H, 13C NMR, IR and HRMS spectra of all novel compounds. Supporting Information File 13: X-ray analysis data of 7b

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

• -benzothiazine derivatives into a carbonic anhydrase inhibition assessment test. The design of the present research work is emphasized by all mentioned pharmaceutical contributions of benzothiazines and adjoining scaffolds. After synthesis following characterization, these new pyrazolobenzothiazine scaffolds

• ethanol. Characterization data Solutions of all synthesized compounds 7a–h were prepared in DMSO-d6 and scanned for their 1H NMR spectra at 300 MHz and 13C NMR spectra at 75 MHz. The characterization data for compounds 7a–h is given in Supporting Information File 1. Antimicrobial assays The antimicrobial

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• 1a,b with pyrimidine-4,6-diols 2e–g. Supporting Information Supporting Information File 2: General synthetic procedures, characterization data and copies of IR spectra, 1H, 13C spectra of all synthesized compounds, as well as 1H-13C HMQC, 1H-13C HMBC spectra and the crystallographic data for

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

• [6], which has to the best of our knowledge not been studied before on its secondary metabolism. The current study deals with the isolation and characterization of the major bioactive principles of the ex-holotype strain of Samsoniella aurantia. Results and Discussion Structure elucidation Compound 1

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• the synthesis and characterization of over 20 new cyanins, reporting their synthetic applications and both calculated and measured their photophysical properties and redox potentials [66]. The study shows that substituents at the central position of the polymethin chain significantly affect their

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

• characterization of all molecules is presented. A detailed assignment of the most relevant Raman bands obtained after vibrational analysis from the theoretical Raman spectrum obtained for the neutral state of m-1 is included in Table S7 of Supporting Information File 1. The most significant Raman feature for the

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 2 and BPP-OiPr 3. Supporting Information Supporting Information File 114: Experimental and computational details, X-ray crystallography, synthesis and characterization of new compounds, additional PL, mass, and NMR spectra, and theoretical calculations. Acknowledgements We appreciate the help

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

• Zhenlei Zhang,
• Ying Wang,
• Xingxing Pan,
• Manqi Zhang,
• Wei Zhao,
• Meng Li and
• Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

• 120 °C for 12 h; yield based on 3. Gram-scale synthesis of 2a and 4a and one-pot synthesis of 4a. Control experiments. Plausible reaction mechanism. Optimization of reaction conditions.a Supporting Information Supporting Information File 110: Experimental procedures, compound characterization data

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• . Optimization of reaction conditions.a Supporting Information Supporting Information File 102: Experimental procedures, product characterization, and copies of NMR spectra. Funding We are grateful to the Scientific Research Project of Hubei Education Department (T2020023 and Q20211402) and the open project of

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

• Asahi Kanno,
• Ryo Tanifuji,
• Satoshi Yoshida,
• Sota Sato,
• Saori Maki-Yonekura,
• Kiyofumi Takaba,
• Jungmin Kang,
• Kensuke Tono,
• Koji Yonekura and
• Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

• by small crystal analysis using an X-ray free-electron laser (XFEL) [54][55]. aSee Supporting Information File 1 for details. Supporting Information Supporting Information File 100: The experimental procedures and characterization data, including copies of NMR spectra and X-ray crystallographic

Quantifying the ability of the CF₂H group as a hydrogen bond donor

• Matthew E. Paolella,
• Daniel S. Honeycutt,
• Bradley M. Lipka,
• Jacob M. Goldberg and
• Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

• correlation between ΔGexp and ELP→σ*. Summary of ΔδDMSO–CDCl3, ΔδDMSO–CD3NO2, and A values of select HB donors.a Supporting Information Supporting Information File 90: Supplementary figures and schemes, materials, experimental procedures; characterization data (1D and 2D NMR, MS, HRMS) for all compounds

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• commercial and in-house developed equipment. Normally, HTE for organic chemistry will include a liquid transfer module, a reactor stage, and analytical tools for product characterization. When the full experimental process is automated and coupled with a centralized control system performing ML optimization

• , Unchained Labs, etc.). In these HTE platforms, microtiter well plates (MTP) and reaction blocks containing 96/48/24-well plates are widely used as reaction and characterization vessels [5]. UltraHTE configurations typically incorporate 1536-well plates, enabling the exploration of lager spaces of reaction

• photocatalytic reactions for water molecule cleavage to produce hydrogen. The mobile robot (Figure 2b) acted as a substitute of a human experimenter by executing tasks and linking eight separate experimental stations, including solid and liquid dispensing, sonication, several characterization equipments, and

Chemical glycobiology

• Elisa Fadda,
• Rachel Hevey,
• Benjamin Schumann and
• Ulrika Westerlind

Beilstein J. Org. Chem. 2025, 21, 8–9, doi:10.3762/bjoc.21.2

• . [12] in the context of photoswitchable ligands to the lectin LecA. Staying in the theme of lectin characterization, Lundstrøm et al. study the glycan binding profile of CMA1 originating from melon [13]. A time that sees great opportunities in computational biology also breeds innovative applications

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

• . This corresponds to a molecular formula of C119H122O9, which is in agreement with the fully fused product 11 in its protonated form. Unfortunately, clean 1H and 13C NMR spectra of this product could not be obtained to allow full characterization of this product. Efforts to increase the yield of 11

• nm) of compound 3 in cyclohexane (1 × 10−5 mol/L). a) Synthesis of 1; b) reactions of 1; c) synthesis of 3. Supporting Information Supporting Information File 63: Experimental details, characterization data, and spectra. Supporting Information File 64: CIF-files of compounds 1 and 3

Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives

• Shuxian Qiu,
• Duan Dong,
• Jiahui Li,
• Huiting Wen,
• Jinpeng Li,
• Yu Yang,
• Shengxian Zhai and
• Xingyuan Gao

Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274

• available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield, especially for the final Cs2CO3-facilitated nucleophilic substitution (77–91% yield). The characterization data obtained from IR and NMR spectroscopy (1H, 13C, 19F, and 31P) as well as

• , starting from commercially available 2-bromo-4-fluoro-1-nitrobenzene under noble-metal-free conditions. The structures and photophysical properties of the desired molecules were also determined. Results and Discussion Synthesis and structural characterization The synthesis of the PhFlOP-based compounds 7

• delight, by treatment of 5 with substituted carbazoles 6 in the presence of Cs2CO3 (5.0 equiv) in DMF at 100 °C, seven 2,8-bis(9H-carbazol-9-yl)-5-phenylbenzo[b]phosphindole 5-oxide derivatives 7 were furnished in good to excellent yields (77–91%). The structural characterization of the obtained molecules

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• , characterization data, and copies of 1H and 13C{1H} NMR spectra. Acknowledgements The data presented in this article are partially taken from the M.Sc. theses of Merve Yence (Bilkent University, 2019) and Dilgam Ahmadli (Bilkent University, 2021). Funding Financial support for some parts of this work from the

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• the electrophilic amination of tert-butyl 3-(p-tolylsulfinyl)propanoate (4a) with BBX 2a (0.23 mmol of limitant in 2 mL of solvent). Supporting Information Supporting Information File 54: Experimental procedures, characterization data, NMR spectra, and X-ray diffraction data. Funding The authors