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Search for "NMR spectra" in Full Text gives 2291 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

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

Graphical Abstract
  • substrates rac-1a–c. Molybdenum-catalyzed asymmetric metathesis dimerization/kinetic resolution of racemic vinylcymantrenes 1a–c.a Supporting Information Supporting Information File 19: Experimental procedures, NMR spectra (1H and 13C) for all the new compounds, and chiral HPLC chromatograms. Supporting
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Published 31 Mar 2026

Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers

  • İlknur Polat,
  • Selçuk Eşsiz and
  • Emine Salamci

Beilstein J. Org. Chem. 2026, 22, 547–556, doi:10.3762/bjoc.22.40

Graphical Abstract
  • to design pharmacological tools in the future. Experimental General information Melting points are uncorrected. Infrared spectra were obtained from solution in 0.1 mm cells or KBr pellets on an FT-IR Mattson 1000 instrument. The 1H and 13C NMR spectra were recorded on 400 (100) MHz Varian or 400 (100
  • (τ, °) in the optimized transition states. Supporting Information Supporting Information File 14: Experimental, 1H and 13C NMR spectra for all new compounds, as well as selected 2D NMR spectra and crystallographic data for compound 10 are provided. Optimized geometries of the transition states with
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Published 26 Mar 2026

Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

  • Horst Weber,
  • Kim-Thao Tran-Cong,
  • Bernhard Mayer,
  • Guido J. Reiss,
  • Iryna S. Konovalova,
  • Marc S. Appelhans,
  • Kenneth R. Wood and
  • Claus M. Passreiter

Beilstein J. Org. Chem. 2026, 22, 535–546, doi:10.3762/bjoc.22.39

Graphical Abstract
  • resolution electrospray ionization mass spectrometry (HRESIMS) and NMR spectra. However, the isomeric compound 3 could not be detected in the extract (Figure 1). Since 4 could be an artefact, built by oxidation of 2 during working up of the extract, and to finally confirm the structure, the isomeric
  • diacetate (EDDA). However, synthesis of 2 was difficult. Despite numerous attempts, we only were able to get mixtures of both melifoliones with minor amounts of 2. Since all attempts to separate both isomers on a preparative scale failed, we were only able to record NMR spectra from a very small quantity of
  • signals detected in the 13C NMR spectrum of 4 (Table 2) could be assigned by careful analysis of the 2D-NMR spectra (HSQC and HMBC). The position of the acetyl group was confirmed by a cross peak between C-2 and the protons of the acetyl-methyl group in the HMBC spectrum and by interactions between the
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Published 24 Mar 2026

Get a better glimpse on sequential photoreactions of trisnorbornadienes with 19F NMR spectroscopy

  • Julian Felix Maria Hebborn,
  • Ben Eric Merten,
  • Thomas Paululat and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2026, 22, 527–534, doi:10.3762/bjoc.22.38

Graphical Abstract
  • analysis. Contrary to the 1H NMR spectra, the 19F NMR spectra show significantly fewer characteristic and sufficiently separated signals that allow the unambiguous identification of all photoproducts and, thus, their detection in the course of the photoreaction. Keywords: fluoroarenes; molecular solar
  • Information File 1, Figure S16). Contrary to the 1H NMR spectra, the 19F NMR spectra showed significantly fewer signals (one or two per molecule) during the photoreaction because of the symmetry of norbornadiene 1f and its photoproducts and the less complex coupling pattern. Thus, the 19F NMR spectra of the
  • circumvented by the application of in situ 19F NMR-spectroscopic measurements. Contrary to the 1H NMR spectra, the 19F NMR spectra are less complex and show characteristic and sufficiently separated signals that allow the unambiguous identification of photoproducts 2f0,3, 2f2,1, and 2f1,2 and, thus, their
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Published 23 Mar 2026

Synthesis and uranyl(VI) extraction performance of a calix[4]pyrrole–tetrahydroxamic acid receptor

  • Sara Karnib,
  • Rana Baydoun,
  • Wissam Zaidan,
  • Nancy AlHaddad,
  • Omar El Samad,
  • Bilal Nsouli,
  • Francine Cazier-Dennin and
  • Pierre-Edouard Danjou

Beilstein J. Org. Chem. 2026, 22, 486–494, doi:10.3762/bjoc.22.36

Graphical Abstract
  • ester substrate. When this method was used, the 1H NMR spectra of the products revealed residual peaks corresponding to unreacted ester (Supporting Information File 1, Figure S8). This observation is consistent with the substrate-dependent behavior reported in that study, highlighting that the reaction
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Published 18 Mar 2026

Structural reassignment of compound 968, an allosteric glutaminase inhibitor

  • Lindsey A. Albertelli,
  • Sainabou Jallow,
  • Chun Li and
  • Scott M. Ulrich

Beilstein J. Org. Chem. 2026, 22, 455–460, doi:10.3762/bjoc.22.33

Graphical Abstract
  • reassigning the structure of the cycloaddition reaction product from benzo[c]phenanthridine 1 to benzo[c]acridine 2, we predicted that all three compounds are the benzo[c]acridine isomer 2. The 1H NMR spectra of all three compounds are identical, indicating that they share the same structure (Figure 3A). We
  • reported to produce benzo[c]phenanthridine 1, of which the commonly accepted structure of 968 is a member. The structure of the product of this reaction was subsequently reported to be the isomeric benzo[c]acridine 2. A) 1H NMR spectra of compound 968 purchased from Sigma-Aldrich (top), the same compound
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Published 13 Mar 2026

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

Graphical Abstract
  • procedures, characterization data, copies of 1H and 13C NMR spectra, and optimized geometries of DFT calculations. Supporting Information File 26: Crystallographic information file of compound 1ac. Acknowledgements We thank K. Imamura (Evaluation center of material properties, IMCE Kyushu University) for
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Published 11 Mar 2026

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

Graphical Abstract
  • 1.80 ppm and one triplet at 3.13 ppm were attributed to the remaining methylene protons located near the selenium atom [51]. In the 13C NMR spectra, distinct chemical shift differences were observed between compounds 7 and 8, due to the small structural differences between them. For compound 7, with
  • F254). Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance 400 MHz FT-NMR and a Bruker Avance III 500 MHz spectrometer. 1H, 13C, and 77Se NMR spectra were acquired in CDCl3, with chemical shifts (δ) reported in ppm. Singlet (s), doublet (d), doublet of doublets (dd), triplet (t
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Published 09 Mar 2026

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

Graphical Abstract
  • tetraureacalix[4]arenes was obtained. Examination of the 1H NMR spectra of the tetraureas in CDCl3 showed that in most cases triazole heterocycles do not intervene the formation of homo- and heterodimeric capsules by these compounds. Thus, considering the synthetic value of CuAAC and amine transformations, p
  • calix[4]arene 11 having four TBS-protected propargyl groups at the narrow rim in only moderate yield of 37% [9]. In our hands, according to the NMR spectra of the reaction mixture, under the reported conditions (>30 equiv of fuming HNO3 per calixarene aromatic unit in a 1:1 dichloromethane/acetic acid
  • only the reaction time increased (Scheme 2). The 1D NMR spectra for the dinitrocalix[4]arenes 12 and 13 provided no definitive data on the substitution patterns at their wide-rims except for the presence of two nitro groups in the distal aromatic units. To localize the nitro groups in the structures of
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Published 09 Mar 2026

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

Graphical Abstract
  • were followed by TLC (Silica gel, aluminum sheets 60 F254, Merck). Melting points were recorded on a Fisher-Johns apparatus. 1H and 13C NMR spectra were recorded on a Varian Mercury spectrometer (400 and 101 MHz, respectively) or Bruker Avance DRX 500 spectrometer (500 MHz and 126 MHz, respectively) in
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Published 03 Mar 2026

Electrosynthetic access to unsymmetrical oxaza[8]helicenes with high chiral stability and strong circularly polarized luminescence (CPL)

  • Tin Zar Aye,
  • Rubal Sharma,
  • Muthu Karuppasamy,
  • Daiya Suzuki,
  • Haruka Nakajima,
  • Yoshitane Imai,
  • Mitsuhiro Arisawa,
  • Mohamed S. H. Salem and
  • Shinobu Takizawa

Beilstein J. Org. Chem. 2026, 22, 372–382, doi:10.3762/bjoc.22.25

Graphical Abstract
  • unsymmetrical oxaza[8]helicenes 5. Chiroptical features of oxaza[8]helicenes 5 and oxaza[7]helicenes 6. Supporting Information Supporting Information File 9: Experimental procedures, synthetic details, NMR spectra, chiral HPLC chromatograms, DFT and TD-DFT calculations. Supporting Information File 10
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Published 25 Feb 2026

Synthesis of tricyclic fused pyrrolidine nitroxides from 2-alkynylpyrrolidine-1-oxyls

  • Mark M. Gulman,
  • Yuliya F. Polienko,
  • Sofia Yu. Trakhininа,
  • Yuri V. Gatilov,
  • Tatyana V. Rybalova,
  • Sergey A. Dobrynin and
  • Igor A. Kirilyuk

Beilstein J. Org. Chem. 2026, 22, 344–351, doi:10.3762/bjoc.22.22

Graphical Abstract
  • nitroxides 2d–f, the samples of the radicals were reduced to the corresponding diamagnetic amines using a Zn/CF3COOH system in CD3OD at 63 °C, according to a literature protocol [23] and the 1H NMR spectra were recorded. The spectra showed similarity to those of previously described for radicals 2a–c [20
  • sulfonate group, respectively [24]. The 1H NMR spectra of 3a,b,d–f (Zn/CF3COOH system in CD3OD) showed appearance of a singlet of methanesulfonate hydrogens in the region from 2.78 to 3.17 ppm. The NMR spectra were not recorded for 3c because of heavy resinification upon the sample preparation. The
  • % yield). The IR spectra of the pyrazole derivatives 9a–c exhibit absorptions at 688–699 cm−1 and 763–770 cm−1, assigned to out-of-plane bending modes of the pyrazole ring [32]. The 1H NMR spectra of the reduction products of pyrazoles 9a–c were recorded after reduction using the Zn/CF3COOH system in
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Published 19 Feb 2026

Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation

  • Arthur A. Puzyrkov,
  • Andrew S. Drachuk,
  • Ekaterina A. Popova,
  • Alexander V. Stepakov and
  • Vitali M. Boitsov

Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20

Graphical Abstract
  • configuration of their stereocenters, was determined using NMR spectroscopy and XRD analysis. endo-Isomers 4a–e exhibited the following characteristic signals in their 1H NMR spectra: multiplets in the range of δ 1.5–4.4 ppm were assigned to the protons of the pyrrolizidine ring system. The methyl singlets of
  • : 4d shows signals at δ 7.12 and 7.30 ppm for ortho- and meta-protons respectively (J = 8.2 Hz) and 4e displays resonances at δ 7.58 and 8.41 ppm for ortho- and meta-protons (J = 8.8 Hz). In the 1H NMR spectra, the proton signals of ring A in diastereomers 4f–p overlap and appear at the same chemical
  • the diastereotopic H6/H6’ methine protons of different atropisomeric forms. The NH protons of the barbiturate ring resonate as broad singlets at δ 11.5–11.7 ppm, while compound 4a shows an additional broad singlet at δ 11.30 ppm corresponding to the succinimide NH group. In the 13C NMR spectra of endo
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Published 17 Feb 2026

Configuration–packing synergy enabling integrated crystalline-state RTP and amorphous-state TADF

  • Ruiyan Wang and
  • Yunan Wu

Beilstein J. Org. Chem. 2026, 22, 224–236, doi:10.3762/bjoc.22.16

Graphical Abstract
  • without further purification. Instruments and measurements Low-resolution mass spectra were recorded on a DSQ electron-impact (EI) mass spectrometer. High-resolution mass spectra (HRMS) were acquired on a Thermo MAT95XP instrument using fast atom bombardment (FAB) ionization. 1H and 13C NMR spectra were
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Published 02 Feb 2026

Synthesis of diaryl phosphates using phytic acid as a phosphorus source

  • Kazuya Asao,
  • Seika Matsumoto,
  • Haruka Mori,
  • Riku Yoshimura,
  • Takeshi Sasaki,
  • Naoya Hirata,
  • Yasuyuki Hayakawa and
  • Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

Graphical Abstract
  • acid molecule (Figure 6 and Figure S3 in Supporting Information File 1) [57][58][59]. The full 1H, 13C, and 31P NMR spectra are provided in Supporting Information File 1. Next, the extracted phytic acid was used for phosphate synthesis. Although the reaction was conducted under the same conditions as
  • (SHIMADZU, Kyoto, Japan) and JMS GC-mate II (JEOL, Tokyo, Japan) instruments. The melting points were determined using a Q-200 differential scanning calorimeter (TA Instruments, New Castle, DE, USA). The NMR spectra were recorded in a deuterated solvent (D2O, methanol-d4 or dimethyl sulfoxide (DMSO)-d6
  • )), and the residual solvent was set to the chemical shift reference for 1H NMR (H2O, δ 4.79 ppm; MeOH, δ 3.31 ppm; DMSO, δ 2.50 ppm). All NMR spectra were compared with those reported in previous studies [15][46][47][48] and found to be consistent with the references. The spectra are provided in
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Published 30 Jan 2026

Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

  • Vladimir G. Ilkin,
  • Margarita Likhacheva,
  • Igor V. Trushkov,
  • Tetyana V. Beryozkina,
  • Vera S. Berseneva,
  • Vladimir T. Abaev,
  • Wim Dehaen and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2026, 22, 192–204, doi:10.3762/bjoc.22.13

Graphical Abstract
  • : Full experimental details and characterization data of all new compounds. Supporting Information File 18: Copies of NMR spectra of all new compounds. Supporting Information File 19: CIF-file for compound 5g. Supporting Information File 20: CheckCIF-file for compound 5g. Funding We gratefully
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Published 28 Jan 2026

Streptoquinolines A and B, new antibacterial meroterpenoids produced by Streptomyces sp. TMPU-A0679

  • Akiho Yagi,
  • Hitomi Tomura,
  • Ami Konno and
  • Ryuji Uchida

Beilstein J. Org. Chem. 2026, 22, 185–191, doi:10.3762/bjoc.22.12

Graphical Abstract
  • . Streptoquinoline B (2): The molecular formula of compound 2 was elucidated as C28H35NO6 based on HRESIMS measurements. The 13C NMR and 1H NMR spectra (in DMSO-d6) of compound 2 showed chemical shift values that were almost identical to those of compound 1 (Table 2). Furthermore, 2D NMR experiments revealed similar
  • Kyokuto Pharmaceutical Co. (Tokyo, Japan). All other chemicals used in this study were of special grade. General experimental procedures HRESIMS spectra were recorded using a mass spectrometer (Xevo G2-XS QTof, Waters Co., Milford, MA, USA). NMR spectra were acquired on a spectrometer (JNM-AL-400; JEOL
  • ) and B (2). Structural elucidation of compounds 1 and 2 by 2D NMR experiments. ROESY correlations of 1. Physicochemical properties of 1 and 2. 1H and 13C NMR chemical shifts in 1 and 2.a MICs of 1 and 2. Supporting Information Supporting Information File 12: MS and NMR spectra of streptoquinolines A
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Published 27 Jan 2026

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

Graphical Abstract
  • bond [21]. When measuring 13C NMR spectra in DMSO-d6 containing different D2O/H2O ratios, isotope effects were clearly observed at several positions (Figure 6c and Figure 6d), with a particularly pronounced upfield shift of the phenol ipso-carbon atom (C14, Δδexp = 0.21 ppm). This two-bond isotope
  • precoated with silica gel 60 F254 (Merck KGaA, Darmstadt, Germany), and retention factors are denoted Rf. Graphs were produced using GraphPad Prism 10.5, except for NMR spectra, where MestReNova was used. ChemDraw 23.1.2 was used to draw chemical structures. Synthesis of 25CN-NBOH·HCl (1·HCl) To a slurry of
  • approach [30]. To ensure gauge independence, nuclear shielding was calculated using the GIAO approach [31][32]. NMR spectroscopy NMR spectra were acquired on a 600 MHz Bruker Avance III HD spectrometer equipped with a 5 mm DCH cryoprobe at 300 K unless otherwise specified. Spectra were processed using
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Published 22 Jan 2026

Asymmetric Mannich reaction of aromatic imines with malonates in the presence of multifunctional catalysts

  • Kadri Kriis,
  • Harry Martõnov,
  • Annette Miller,
  • Mia Peterson,
  • Ivar Järving and
  • Tõnis Kanger

Beilstein J. Org. Chem. 2026, 22, 151–157, doi:10.3762/bjoc.22.8

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  • 20: Experimental procedures, synthetic details, NMR spectra, chiral HPLC chromatograms. Funding The research was funded by the Estonian Ministry of Education and Research (grant No. PRG1031).
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Published 16 Jan 2026

Design and synthesis of an axially chiral platinum(II) complex and its CPL properties in PMMA matrix

  • Daiki Tauchi,
  • Sota Ogura,
  • Misa Sakura,
  • Kazunori Tsubaki and
  • Masashi Hasegawa

Beilstein J. Org. Chem. 2026, 22, 143–150, doi:10.3762/bjoc.22.7

Graphical Abstract
  • and 13C NMR spectra were recorded on a Bruker Avance III 400 or JEOL JNM-ECZ600R spectrometer at 25 °C in chloroform-d1 or DMSO-d6. 1H NMR chemical shifts are expressed in parts per million (δ) relative to trimethylsilane (TMS) as a reference. Mass spectra were obtained with a Thermo Scientific
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Published 15 Jan 2026

Highly electrophilic, gem- and spiro-activated trichloromethylnitrocyclopropanes: synthesis and structure

  • Ilia A. Pilipenko,
  • Mikhail V. Grigoriev,
  • Olga Yu. Ozerova,
  • Igor A. Litvinov,
  • Darya V. Spiridonova,
  • Aleksander V. Vasilyev and
  • Sergey V. Makarenko

Beilstein J. Org. Chem. 2026, 22, 123–130, doi:10.3762/bjoc.22.5

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  • use of method E in the reaction of 1-bromo-1-nitro-3,3,3-trichloropropene (1) with methyl cyanoacetate, ethyl cyanoacetate or benzoylacetonitrile makes it possible to obtain cyclopropanes 3–5 in the yields up to 72% (Scheme 2). They are formed as single diastereomers (according to the 1H NMR spectra
  • Diffraction Research Methods of the A. E. Arbuzov Institute of Organic and Physical Chemistry, the Kazan Scientific Center of the Russian Academy of Sciences. The 1H-13C{1H}, 1H-1H dqfCOSY, 1H-1H NOESY, 1H-13C HMQC, 1H-13C HMBC NMR spectra were recorded on a Jeol ECX400A spectrometer operating at 399.78 MHz
  • the structure are shown in Table S1 in Supporting Information File 1. Supporting Information File 14: General synthetic procedures, characterization data and copies of IR spectra, 1H-13C{1H}, 1H-1H dqfCOSY, 1H-1H NOESY, 1H-13C HMQC, 1H-13C HMBC NMR spectra of all synthesized compounds, and
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Published 14 Jan 2026

Reactivity umpolung of the cycloheptatriene core in hexa(methoxycarbonyl)cycloheptatriene

  • Dmitry N. Platonov,
  • Alexander Yu. Belyy,
  • Rinat F. Salikov,
  • Kirill S. Erokhin and
  • Yury V. Tomilov

Beilstein J. Org. Chem. 2026, 22, 64–70, doi:10.3762/bjoc.22.2

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  • , quantum chemical calculation details and copies of NMR spectra. Funding This work was financially supported by the Russian Science Foundation (Grant No. 25-23-00616).
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Published 05 Jan 2026

Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides

  • Alexander S. Budnikov,
  • Nikita E. Leonov,
  • Michael S. Klenov,
  • Andrey A. Kulikov,
  • Igor B. Krylov,
  • Timofey A. Kudryashev,
  • Aleksandr M. Churakov,
  • Alexander O. Terent’ev and
  • Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2025, 21, 2739–2754, doi:10.3762/bjoc.21.211

Graphical Abstract
  • hygroscopic nature. Any manipulations must be carried out by using appropriate standard safety precautions. 1H, 13C, 14N NMR spectra were recorded with Bruker DRX-500 (500.1, 125.8, 36.1 MHz, respectively) and Bruker AV600 (600.1, 150.9, 43.4 MHz, respectively) spectrometers. Chemical shifts are reported in
  • all compounds, XRD of 2c, computational details, and copies of 1H, 13C, 14N, 1H,13C HSQC, and 1H,13C HMBC NMR spectra. Supporting Information File 5: Crystallographic information for compound 2c. Supporting Information File 6: CheckCIF report for the data of 2c. Acknowledgements Crystal structure
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Published 29 Dec 2025

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

Graphical Abstract
  • –1628 cm−1 and NH2 groups at ν 3376–3272 cm−1. The structures of the obtained heterocycles 4 and 5 contain three stereocenters, so one could expect the formation of up to 8 stereoisomers in each case. Analysis of the 19F NMR spectra showed that from two to four diastereomers of
  • crystal 4a–d and 5a–c are in excellent agreement with the results of 1D and 2D NMR studies, enabling us to extend these structural assignments to other synthesized bicycles. The complete assignment of signals in 1H and 13C NMR spectra was performed using two-dimensional 1H-1H COSY, NOESY and 1H-13C HSQC
  • , whereas in the trans-configuration of the hexahydropyrimidine ring, a cross-peak (OHax, H(2)eq) appears in the spectrum. In the 1H NMR spectra of octahydropyrido[1,2-a]pyrimidinones 4att, 4a–dct, which have the trans-configuration of the hexahydropyrimidine ring, the signal of the H(3) proton has the form
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Published 17 Dec 2025

Tandem hydrothiocyanation/cyclization of CF3-iminopropargyl alcohols with NaSCN in the presence of AcOH

  • Ruslan S. Shulgin,
  • Ol’ga G. Volostnykh,
  • Anton V. Stepanov,
  • Igor’ A. Ushakov,
  • Alexander V. Vashchenko and
  • Olesya A. Shemyakina

Beilstein J. Org. Chem. 2025, 21, 2694–2702, doi:10.3762/bjoc.21.207

Graphical Abstract
  • formation and ratio of the products in contrast to the substituents in the imine fragment. NMR monitoring of reactions (1a/NaSCN/AcOH or 1g/NaSCN/AcOH in MeCN) did not allow to detect any intermediates even when the temperature was lowered to 0 °C. In the 1H and 19F NMR spectra the signals of products 2a
  • and 3a appeared immediately upon mixing the starting reagents (Figure 1a and b). This indicated that the cyclization occurred almost immediately. Moreover, in the NMR spectra of the 1g/NaSCN/AcOH reaction mixture in MeCN we detected signals assigned to isothiozolium salt 2g (1H NMR: δ 8.30 s (CH
  • operational simplicity, relatively mild conditions and readily prepared starting materials. Experimental General information. 1Н, 13С {1H}, and 19F NMR spectra were recorded on a Bruker DPX-400 spectrometer (400.1, 100.6, and 376 MHz, respectively) in CDCl3 and (CD3)2CO using hexamethyldisiloxane (HMDS) as
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Published 16 Dec 2025
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