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

• -disubstituted pyrrolidine-2,3-diones were successfully synthesized via reversible transimination reaction. The structure of all compounds was evaluated using nuclear magnetic resonance (NMR) spectroscopy and, especially, with the molecular structure of compound 5a further confirmed through single-crystal X-ray

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

• tools, UV–vis and NMR spectroscopy were utilized. We determined significant spectral features of the formed NBD species, including λmax and λonset values, all of which exhibit redshifts compared to their isocyclic counterparts. Additionally, the selected QC isomers were subjected to thermal and

• characterized using UV–vis and NMR spectroscopy, as well as high-resolution mass spectrometry. An overview of the synthetic and spectroscopic data for all derivatives is provided in Table 1, while the specific spectroscopic properties of the individual QC analogues can be found in Supporting Information File 1

• . Photoswitching The photoswitching of the NBDs to corresponding QCs was monitored by UV–vis and 1H NMR spectroscopy. With increasing electronegativity of the bridge-atom, a slight bathochromic shift in the absorption spectra of the parent NBD precursors O-NBD1 and N-NBD1 was found (Figure 2a and 2c). For the

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

• Leon M. Friedrich and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

• thermodynamically stable EE isomer was followed over time starting from the PSS@365 nm. The kinetic traces of the relaxation process were recorded by 1H NMR spectroscopy at 37 °C (Supporting Information File 1, Figure S2) and the population of the EE, ZE, EZ, and ZZ isomers were plotted against time. Using a

• glycocluster 1 [24] and the homobivalent azobenzene glycocluster 6αMan3αMan 2 and the glycoazobenzene-functionalized individual antennas 6αMan 3, 6βGlc 4, and 3αMan 5. The PSS was reached after irradiation with light of the denoted wavelength for 5 min and determined by NMR spectroscopy. Rate constants (k

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

• ). 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

• -association in phosphate-buffered saline (PBS) which might impinge on guest binding and complicate the determination of C1·guest binding constants. For this purpose, we performed dilution experiments monitored by 1H NMR spectroscopy. We prepared a series of NMR samples of C1 in D2O (from 4 mM to 125 μM) and

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

• Scheme 1 and Scheme 2. The newly synthesized compounds were characterized by NMR spectroscopy as well as elemental analysis or high-resolution mass spectrometry. The experimental details and compound data are provided in Supporting Information File 1. Aldehyde 4, in which one of the formyl groups in

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

• , 13C NMR spectroscopy and high-resolution MS. 1H NMR spectra of obtained products contain characteristic signals of the protons of the methyl group in the region δ 1.72–2.16 ppm and proton of pyranone fragment in the region δ 5.98–6.62 ppm. Besides that, the key structures of synthesized products were

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

• for the construction of contiguous tetrasubstituted carbon centers via the Mannich reaction and this work. Plausible reaction mechanism. Catalyst screening for the asymmetric Mannich reaction. All yields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as an internal standard. N

• -Protecting group optimization for the asymmetric Mannich reaction. All yields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as an internal standard. aReaction conducted for 24 h. Catalyst screening using 7b as a substrate. All yields were determined by 1H NMR spectroscopy using 1,3,5

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

• photochemical reaction. Its structure was elucidated by NMR spectroscopy and single crystal X-ray diffractometry. The latter revealed no π–π interaction between neighboring ANTH cores. A combination of high photoluminescence quantum yield (PLQY) of 0.85 for 9,10-ANTH(BnF)2, its significantly improved

Synthesis of the aggregation pheromone of Tribolium castaneum

• Biyu An,
• Xueyang Wang,
• Ao Jiao,
• Qinghua Bian and
• Jiangchun Zhong

Beilstein J. Org. Chem. 2025, 21, 510–514, doi:10.3762/bjoc.21.38

• of (R)-2-methyloxirane ((R)-2) with allylmagnesium bromide (3) catalyzed by CuI produced a mixture of (R)-hex-5-en-2-ol ((R)-4) and (S)-2-methylpent-4-en-1-ol ((S)-4’) (ratio 8:1, determined by 1H NMR spectroscopy) [25][26]. The primary alcohol (S)-4’ could be easily removed by a selective TEMPO

• the aggregation pheromone (4R,8S)-1, (4S,8R)-1, and (4S,8S)-1 were prepared through Li2CuCl4-catalyzed coupling and oxidation with RuCl3/NaIO4 from chiral building blocks (R)-10, (S)-10, (R)-11 and (S)-11, which were characterized by NMR spectroscopy and HRMS. Conclusion In summary, we have achieved a

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• agent 2.2 in a sub-stoichiometric fashion (20 mol %). However, even upon prolonged exposure, the yield of 2.3 did not exceed 20% (by 1H NMR spectroscopy). To achieve turnover, the photoreacted solid was subjected to a second grinding and exposed again to UV irradiation for an additional 16 h, which

• resulted in 40% yield. Alternating grinding and irradiation, the authors managed to obtain quantitative conversion of 2.1 to 2.3. Overall, in this work, mechanochemistry worked akin to agitation provided by stirring or heating in solution. In fact, 1H NMR spectroscopy, XRD and DFT analyses showed that

• when a 1:1 mixture of p-di[2-(4-pyridyl)ethenyl]benzene (5.1) and 4-benzylresorcinol (5.2) was ground with a mortar and pestle (1 h) and then irradiated with a low-pressure Hg lamp (60 h), [2.2]paracyclophane (5.3) was formed in poor yield (35% by 1H NMR spectroscopy). Dry vortex grinding did not

Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2’-dibromobiphenyls

• Andrejs Savkins and
• Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

• improving the substrate scope and understanding the reaction mechanism are in progress in our laboratory. Synthesis of cyclic diarylbromonium compounds. Substrate scope. Reactions were performed on a 0.15 mmol scale. Yields were determined by 1H NMR spectroscopy of the reaction mixture using 1,2,3,4

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

• Yuriy I. Horak,
• Roman Z. Lytvyn,
• Andrii R. Vakhula,
• Yuriy V. Homza,
• Nazariy T. Pokhodylo and
• Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

• products were identified via NMR as 4,4a,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindoles. The structures of compounds 5 were confirmed by NMR spectroscopy data (for details and discussion see Supporting Information File 1). The NMR data for the obtained furoindole skeleton signals and spin-coupling constants

• these compounds were confirmed by NMR spectroscopy (see Supporting Information File 1). Conclusion In summary, we showed the practical usage of 3-(furan-2-yl)acrylaldehyde in the four-component Ugi reaction with the prospect of further intramolecular [4 + 2] cycloaddition of the Ugi reaction product. We

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

• investigated the role of the C-2 protecting group in Schmidt’s trichloroacetimidate glycosylation with donor 60 which showed excellent yield along with the formation of the 1,2-trans glycoside only. They proposed the mechanism with the help of NMR spectroscopy and the studies revealed that the N

• species was confirmed by low temperature NMR spectroscopy. Similarly, Ito et al. also introduced the concept of using 2-O-(o-tosylamido)benzyl (TAB)-modified donor 103 for the stereocontrolled synthesis of both 1,2-cis and 1,2-trans glycosides under modified reaction conditions [154][155]. They

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

• reaction of o-chloranil with benzoannelated derivatives of 2,3,3-trimethylindolenine, a comprehensive evaluation of the structure of the compounds obtained using quantum chemical methods, X-ray diffraction analysis, two-dimensional correlation NMR spectroscopy, as well as investigation of their ionochromic

• proton is shifted to a stronger field of 14.23 ppm and appears as a narrow singlet (Supporting Information File 2, Figure S17). Analysis of two-dimensional correlation spectra of heteronuclear NMR spectroscopy shows that compound 7a in DMSO-d6 solution exists in the (NH) tautomeric form. Thus, in the 1H

• -ray diffraction analysis. Using two-dimensional correlation NMR spectroscopy methods, it was shown that the nature of the solvent significantly affects the equilibrium of the tautomeric forms of the 1,3-tropolones. The obtained compounds represent molecular switches of optical and fluorescent

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

• and 13C NMR spectroscopy. All compounds were tested against five human microbial strains including three different strains of Staphylococcus aureus (ATCC 25923, ATCC BAA-41, and ATCC BAA-44), Escherichia coli (ATCC 8739), and Candida albicans (ATCC 90027) to evaluate their antibiotic potential. The

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

• -dihydronaphtho[1,2-b]furan-3-carboxylate 4a,b with a total yield of up to 73% (ratio 3a/4a = 2:1; 3b/4b = 2:1, according to 1H NMR spectroscopy) (Scheme 4). Using preparative chromatography, the mixture was separated into individual substances. In turn, alkyl 7,7-dimethyl-4,9-dioxo-6,7,8,9-tetrahydro-4H-furo[3,2

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

• . Supporting Information Supporting Information File 6: HRESIMS profiles and NMR spectroscopic data of compounds 1–6. Acknowledgements The authors thank S. Reinecke, C. Kakoschke, E. Surges and W. Collisi for their generous technical assistance, acquiring HRESIMS, NMR spectroscopy, antimicrobial and

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

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• an important role; the presence of the condensation catalyst ʟ-proline accelerated the absorption of formaldehyde vapors by the reaction mixture. Carrying out the same reaction in the absence of a catalyst in CDCl3 and subsequent 1H NMR spectroscopy analysis showed that the mixture contained 42% of

• cyanoacetic ester and acetylacetone. The configuration of the products 4 and 5 was established by bromination of a small amount of these isomeric compounds in CDCl3 (Scheme 6) and subsequent analysis of the mixture by 1H NMR spectroscopy. For the stereoisomers 4, the main product was lactone 22, identified by

• [27]. The three-component reaction with acetoacetic ester was highly selective, and the formation of a minor [4 + 2]-cycloaddition product was not observed (according to 1H NMR spectroscopy), but the yield of the products 15 did not exceed 9%. For acetylacetone, the reaction was the least selective

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

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

• a fluorescent intermediate 18, and subsequent ring opening allowed a streamlined one-pot access to the substructure of THIQ alkaloids 14 in a good yield of 60% from 11. The structure of the resulting 14 was elucidated through comprehensive two-dimensional NMR spectroscopy, complemented by NOE

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

• donation ability of the CF2H group by 1H NMR titration with tri-n-butylphosphine oxide (n-Bu3PO) as a reference HB acceptor (Figure 4A and Figures S20–S40 in Supporting Information File 1). Unlike a previous method that relied on 31P NMR spectroscopy [52], our titration monitors the HB complex formation by

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

• molar ratio observed in ESI experiments. These inspiring results prompted us to further examine the interaction between host H1 and G1 by 1H NMR spectroscopy. Our prior experience with cyclo[6]aramide has confirmed binding to the cationic guest [49]. Indeed, addition of compound H1 to the guest solution

• mixture of G2 and zinc salt in CHCl3/CH3CN (1:1, v/v) was subjected to 1H NMR spectroscopy. Protons H2–H4, H7, H8, H11, and H12 of G2, located around the metal coordination site, were found to experience upfield or downfield shifts to a varying extent (Figure S8, Supporting Information File 3

• , which is characteristic for the formation of supramolecular polymers. The concentration-dependency of a mixture of H1, G2, and zinc salt was examined by variable-concentration NMR spectroscopy. Pronounced broadening of signals was observed (Figure 8), which clearly indicated increasing polymerization

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

• Takeshi Fujita,
• Haruna Yabuki,
• Ryutaro Morioka,
• Kohei Fuchibe and
• Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

• , excluding boronic acid 2a (Scheme 6). The reaction was monitored using 19F and 31P NMR spectroscopy. The 19F NMR analysis showed that 79% of 1b remained and revealed a new broad double doublet peak at 55.0 ppm (JFP = 53, 42 Hz) relative to internal C6F6 (δ = 0.0 ppm). The 31P NMR spectrum depicted broad

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

• four-step process involves allylation, Claisen rearrangement, isomerization, and oxidative dimerization. Each reaction step was optimized independently by using either online HPLC or in-line benchtop NMR spectroscopy to afford an overall yield of 67% in 66 iterative experiments over four linear