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

• % yield. Alcohol products, [4.3.3]_CH2OH and [3.3.3]_CH2OH, were then tested in acidic conditions using anhydrous FeCl3 as a Lewis acid. After the reactions, the alcohol proton signals at 1.54–1.58 ppm disappeared in the 1H NMR spectra, and aliphatic carbon ones at 63.1–63.2 ppm were largely up-field

• -shifted to ca. 34 ppm in the 13C NMR spectra due to conversion into methylene groups (Figure 2b and Figures S315 and S316 in Supporting Information File 1). However, all 1H NMR signals were broad, and gel permeation chromatography (GPC) charts indicated broad patterns due to multiple products with varying

• electrophilic functionalization. a) Synthesis of methylene-alternating copolymers of fully π-fused propellanes. DCE, 1,2-dichloroethane. b) 1H NMR (500 MHz, top) and 13C (126 MHz, bottom) NMR spectra of [4.3.3]_CH2OH and [4.3.3]_linear in CDCl3 at room temperature. Gas adsorption (filled circles) and desorption

A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones

• Ashutosh Nath,
• John Mark Awad and
• Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92

• -aromatization. Optimization of IMDA and re-aromatization reactions for the preparation of 8a. Supporting Information Supporting Information File 50: General reaction procedures, compound characterization data, and copies of NMR spectra. Conflict of Interest The authors declare no competing financial interest.

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

• General experimental Melting points were measured using a Cole-Parmer (Chicago, IL, USA) melting point apparatus and were uncorrected. UV spectra were recorded using an Ocean Optics (USB-ISS-UV/VIS) spectrophotometer. NMR spectra were recorded at 25 °C on a Bruker (Billerica, MA, USA) AVANCE III™ HD 500

• cell line HEK293. Supporting Information Supporting Information File 44: Complete experimental methods, crystallographic data for 2, 7, 10 and 15, characterisation data and 1D/2D NMR spectra (1H, 13C, COSY, HSQC and HMBC) for 2–15. Acknowledgements The authors wish to thank and acknowledge the

A versatile route towards 6-arylpipecolic acids

• Erich Gebel,
• Cornelia Göcke,
• Carolin Gruner and
• Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 1104–1115, doi:10.3762/bjoc.21.88

• after workup. Purifying the bromide 2 via column chromatography was deemed unnecessary after comparing the NMR spectra of the worked-up and the purified product. While the worked-up product 2 exhibited only slight differences in impurities, the yield was significantly reduced due to purification by

• favourable chair conformation with the aryl substituent and the methyl ester in equatorial positions (Figure 3), providing further evidence for conformational restraints (pseudoallyl strain) enforced by the formyl group. This behaviour is observable in all NMR spectra of the compound array of the reduction

• ). Analysing the 1H NMR spectra of reduction product (2R,6S)-13 reveals a very similar pattern to the previously discussed Suzuki–Miyaura product (2R,6S)-9 with one significant distinction. The signals of both protons H2 and H6 of the first conformer (2R,6S)-13I in comparison to the second one (2R,6S)-13II are

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

• NaBArF24. Supporting Information Supporting Information File 29: Detailed experimental procedures, NMR spectra, and X-ray crystallography details. Supporting Information File 30: Crystallographic Information Files for 1/LiBArF20 and 1/NaBArF24. Funding We thank the National Science Foundation (#2003654

Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes

• Linqiang Wang and
• Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86

• mechanism. Gram-scale synthesis. Optimization of reaction conditions.a Supporting Information Supporting Information File 24: Analytic data and copies of 1H and 13C NMR spectra of compounds 1 and 3, copies of HRMS spectra of unknown compound 3 and copies of HLPC profiles of compounds 3. Funding This

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

• Valentina Benazzi,
• Arianna Bini,
• Ilaria Bertuol,
• Mariangela Novello,
• Federica Baldi,
• Matteo Hoch,
• Alvise Perosa and
• Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

• voltammetry of triarylsulfonium salts and NMR spectra. Funding Fondazione Cariplo (Photo and Mechano-Chemistry for the Upgrading of Agro- and Sea-food Waste to advanced polymers and nanocarbon materials, CUBWAM, project 2021–0751).

Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality

• Natsume Akimoto,
• Kaho Takaya,
• Yoshio Kasashima,
• Kohei Watanabe,
• Yasushi Yoshida and
• Takashi Mino

Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83

• allylic amination of acetate 12 with isatin (11a).a Supporting Information Data of thermal racemization of 7, DFT calculations for investigating racemization mechanism of 7, general methods and materials, experimental procedures and characterization data, 1H, 13C and 31P NMR spectra for 9 and 10, 1H, 13C

• and 31P NMR spectra and HPLC charts for (±)-7, (+)-7 and (–)-7, 1H and 13C NMR spectra and HPLC charts for (S)-13a–k (except (S)-13e) and (S)-16. Supporting Information File 18: Experimental section and compounds characterization. Funding This work was supported by a Grant-in-Aid for Scientific

Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

• Benedek Batizi,
• Patrik Pollák,
• András Dancsó,
• Péter Keglevich,
• Gyula Simig,
• Balázs Volk and
• Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

• request/cif. Supporting Information File 6: ORTEP diagram of compound 31, synthetic procedures, IR, 1H, 13C, 19F and 2D NMR spectra of compounds 2, 5, 6, 24–28 and 30–32. Supporting Information File 7: Crystallographic information file of compound 31. Supporting Information File 8: Checkcif file for

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

• functional group compatibility. Supporting Information Supporting Information File 2: Additional experimental details including reaction procedures, X-ray crystallographic data, and NMR spectra of synthesized compounds. Acknowledgements Justin Douglas and Sarah Neuenswander (KU NMR Lab) are acknowledged

Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts

• Katy Medrano-Uribe,
• Jorge Humbrías-Martín and
• Luca Dell’Amico

Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76

• NMR spectra. Acknowledgements L. D. and K. M. U. thank Dr. Ilaria Fortunati for her technical support during the lifetime measurements. Funding The financial support of the authors is provided by the Ministero dell'Università e della Ricerca (MUR, C93C22007660006, K.M.U), Fondazione Cariparo

A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

• Zhiyang Zhang,
• Jialei Hu,
• Hanfeng Ding,
• Li Zhang and
• Peirong Rao

Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75

• crystallographic data for this paper. These data can be obtained free of charge via the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service. Supporting Information File 8: Experimental procedures, NMR spectra and other characterization data for all

Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines

• Muhammad Hasan,
• Anatoly A. Peshkov,
• Syed Anis Ali Shah,
• Andrey Belyaev,
• Chang-Keun Lim,
• Shunyi Wang and
• Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2025, 21, 915–925, doi:10.3762/bjoc.21.74

• characterization data and the copies of NMR spectra. Acknowledgements We gratefully acknowledge the National Natural Science Foundation of China (No. 21971174 and 21906114), Nazarbayev University Faculty-Development Competitive Research Grants Program (11022021FD2903), Nazarbayev University Collaborative Research

Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions

• Wen-Hui Mi,
• Teng-Yu Huang,
• Xu-Dong Wang,
• Yu-Fei Ao,
• Qi-Qiang Wang and
• De-Xian Wang

Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72

• ) Crystal structure of B4aH (hydrogen atoms are omitted for clarity), and (c) the stacking structure of the crystal of B4aH (the blue dotted lines represent hydrogen bonds). (a) The structures of host and guests, (b) 1H NMR spectra (298 K, 400 MHz, CD3CN) of B4aH upon titration with C62− (c(B4aH) = 1 mM

Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes

• Patricia Gómez-Roibás,
• Andrea Chaves-Pouso and
• Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71

• )cyclopropanes by base-promoted intramolecular cyclization. Supporting Information Supporting Information File 2: Experimental procedures, characterization data and copies of NMR spectra. Funding Financial support from the AEI (PID2020-118237RB-I00), European Research Council (863914), Xunta de Galicia (ED431C

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

• for clarity. Stacked 1H NMR spectra of (a) free anion receptor L and its complexes with one equivalent of (b) Cs2SO4, (c) Cs2CO3, and (d) Cs3PO4 in the presence of 18-crown-6 (DMSO-d6, 1 mM, 400 MHz, 298 K). Single crystal structure of complexed Cs2CO3 (CCDC: 2411574) with 18-crown-6 and tripodal

• Cs+ is stabilized by six ion-dipole interactions from carbonyl (O=C) and nitro (-NO2) groups. The overall stoichiometry of Cs+, CO32−, 18-crown-6 and anion receptor is 2:1:1:1. Nonpolar hydrogen atoms and solvent molecules are omitted for clarity. (b) Stacked 1H NMR spectra of free anion receptor L

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

• Xuhong Zhao,
• Weishuang Li,
• Mengli Yang,
• Bojie Li,
• Yaoyao Zhang,
• Lizhen Huang and
• Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

• ). Optimization of reaction conditionsa. Supporting Information Supporting Information File 48: Full experimental details, characterization data and copies of NMR spectra of all products. Funding This work was financially supported by Project of Science and Technology Research of Hubei Provincial Department of

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

• equipment, experimental procedures, compound characterization, UV–vis spectra at different concentrations, photochemical experiments, thermal isomerization analysis, and NMR spectra. Funding We thank the Swedish Vetenskapsrådet for a Starting Grant (2021-05414 to SC and to 2023-04088 to NAS). This work was

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

• determine the melting points of all products. All NMR spectra were recorded on a Bruker Avance II+ 600 MHz instrument and chemical shifts (δ) are reported in ppm (parts per million) relative to tetramethylsilane (TMS) or internal deuterated solvent signals. Computational methods Prediction of drug-likeness

Synthesis and photoinduced switching properties of C₇-heteroatom containing push–pull norbornadiene derivatives

• Daniel Krappmann and
• Andreas Hirsch

Beilstein J. Org. Chem. 2025, 21, 807–816, doi:10.3762/bjoc.21.64

• N-UnS1 monitored via NMR spectroscopy in CDCl3. Rearrangement of O-NBD2 to O-QC2 using a 385 nm LED. The UV–vis measurement in the middle were conducted in MeCN, NMR spectra at the bottom with 6.9 mg substance in 650 μL CDCl3. Prolonged irradiation resulted first in the formation of an unidentified

• species O-UnS2 (after 60 min) and further unknown rearrangement combined with photodecomposition after 18 h. Rearrangement of N-NBD2 using a 385 nm LED. The UV–vis measurement in the middle were conducted in MeCN, NMR spectra at the bottom with 6.9 mg substance in 650 μL CDCl3. Generation of the new

• Information Supporting Information File 42: Experimental, characterization data, copies of NMR spectra and switching experiments. Funding The authors acknowledge financial support provided by the Deutsche Forschungsgemeinschaft (DFG) as part of the project “Molekulares Management von Sonnenenergie - Chemie

Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives

• Qingqing Jiang,
• Xinyi Lei,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2025, 21, 749–754, doi:10.3762/bjoc.21.58

• Supporting Information Supporting Information File 30: Experimental procedures, characterization data for all new compounds, and NMR spectra of products. Funding We are grateful for the financial support from the China Postdoctoral Science Foundation (2021M692713) and the Natural Science Foundation of

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

• column chromatography was purchased from Macherey-Nagel. 1H and 13C NMR spectra were recorded on a Bruker UltrashieldTM 400 MHz Plus or a 700 MHz Avance Neo spectrometer. Chemical shifts (δ) are reported relative to tetramethylsilane (TMS), referenced to the residual solvent signal (DMSO-d6: 2.50 ppm for

• 1H NMR and 39.52 ppm for 13C NMR spectra; CDCl3: 7.26 ppm for 1H NMR and 77.16 ppm for 13C NMR spectra). Signal assignments are based on 1H-1H-COSY, 1H-13C-HSQC and 1H-13C-HMBC experiments. High-resolution mass spectra were recorded in positive ion mode unless otherwise noted on a Thermo Scientific Q

• (pulldown of circular Pepper RNA from total RNA of HEK 293T cells) see reference [11]. Supporting Information Supporting Information File 26: Experimental, characterization data and copies of NMR spectra. Funding This work was funded in part by the Austrian Science Fund FWF [P31691, F8011-B] and 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

• used without further purification. Guest molecules were available from previous studies [65][71]. Compounds TetW1OAc and TetW1 were prepared according to the literature procedures with slight modifications [70]. NMR spectra were recorded using commercial spectrometers operating at 600 or 400 MHz for 1H

• , 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

• spectra of the fluorescence, synthetic procedures and physical data for the new compounds, theoretical calculation results, copy of 1H and 13C NMR spectra of the prepared compounds. Acknowledgements HO thanks Prof. Kan Wakamatsu (Okayama University of Science) for fruitful discussions and Prof. Takayoshi

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

• Maurizio Iannuzzi,
• Thomas Hohmann,
• Michael Dyrks,
• Kilian Haoues,
• Katarzyna Salamon-Krokosz and
• Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

• Schlenk vessels at a Schlenk unit/oil pump vacuum under nitrogen atmosphere. The stated reaction temperatures are the respective values of the silicone oil heating bath. All reactions were stirred with an electric magnetic stirrer. 1H, 13C, and 19F NMR spectra were measured at room temperature with a JEOL

• 11a and 11b. Supporting Information Supporting Information File 18: NMR spectra and HPLC chromatograms.