Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• treated with 90% aq trifluoroacetic acid in CH2Cl2 to give diol 7 (70% yield) that was formed due to migration of a chloroacetyl group from O-7 to O-9. The structure of diol 7 was established by NMR spectroscopy, high-resolution mass spectrometry and X-ray diffraction analysis (see the Experimental

• CFCl3 (δF 0.0). Assignments of the signals in the NMR spectra were performed using 2D-spectroscopy (COSY, HSQC, HMBC) and DEPT-135 experiments. For the copies of NMR spectra for all new compounds see Supporting Information File 1. High resolution mass spectra (electrospray ionization, HRESIMS) were

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• reported to one decimal point unless an additional digit was required to distinguish overlapping peaks. Software for data processing: MestReNova, version 11.0.0–17609 (MestReLab Research S.L.). High-resolution mass spectrometry (HRMS) data were recorded on a Waters Micromass LCT LC–TOF instrument using

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• in TCBDs and DCNQs and their optical resolutions were first realized in 2010 through their conjugation with methylated fullerenes, as shown in Figure 2 [130]. The optical resolution was realized using a chiral high-performance liquid chromatography (HPLC) system equipped with an (S,S)-WHELK-O1 column

• when the TCBD moiety was incorporated at the axial position of the subphthalocyanine (SubPc) core (Figure 3) [131]. Axially chiral SubPc–TCBD–aniline conjugates 59 and 60 were characterized via optical-resolution analysis through chiral HPLC using a Chiralpak IC column. The researchers unequivocally

• types of subporphyrin derivatives 61 and 62, wherein the subporphyrin skeleton was functionalized at its meso or axial position with the TCBD moiety (Figure 3). Although the optical resolution of 61 failed, they succeeded in achieving the optical resolution of 62 via chiral HPLC using a Chiralpak IC

Visible-light-induced radical cascade cyclization: a catalyst-free synthetic approach to trifluoromethylated heterocycles

• Chuan Yang,
• Wei Shi,
• Jian Tian,
• Lin Guo,
• Yating Zhao and
• Wujiong Xia

Beilstein J. Org. Chem. 2024, 20, 118–124, doi:10.3762/bjoc.20.12

• NMR (Figure S3 in Supporting Information File 1) [30] and high-resolution mass spectrometry. You and co-workers proposed a reaction pathway involving the combination of the indole substrate and Umemoto’s reagent to form an electron donor–acceptor (EDA) complex [31]. We excluded the possibility of an

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• current: 3.5 kV, capillary temperature: 300 °C, capillary voltage: 45 V, injection rate: 5 μL/min, scanning range: 150−750 m/z, and resolution: ultra-high) and processed with the software Xcalibur. The CHNS analysis data were determined in-house with a HEKAtech EuroEA combustion analyzer. The melting

Electron-beam-promoted fullerene dimerization in nanotubes: insights from DFT computations

• Laura Abella,
• Gerard Novell-Leruth,
• Josep M. Ricart,
• Josep M. Poblet and
• Antonio Rodríguez-Fortea

Beilstein J. Org. Chem. 2024, 20, 92–100, doi:10.3762/bjoc.20.10

• molecules on surfaces like graphene or carbon nanotubes have allowed the scientific community to visualize at atomic resolution the structural changes of molecules in situ by single-molecule atomic-resolution real-time TEM imaging (SMART-TEM) [1][2][3][4][5]. Since the initial discovery [2], many movies

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

• Pengcheng Li,
• Daniel Kowalczyk,
• Johannes Liessem,
• Mohamed M. Elnagar,
• Dariusz Mitoraj,
• Radim Beranek and
• Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

• substrate and allowed to dry at room temperature. To improve the conductivity and achieve higher resolution SEM imaging, a 20 nm thick layer of Au was sputtered onto the sample surface. For EDS mapping, the samples were not sputtered with Au to avoid interference during the determination of Pt. UV–vis

NMRium: Teaching nuclear magnetic resonance spectra interpretation in an online platform

• Luc Patiny,
• Hamed Musallam,
• Alejandro Bolaños,
• Michaël Zasso,
• Julien Wist,
• Metin Karayilan,
• Eva Ziegler,
• Johannes C. Liermann and
• Nils E. Schlörer

Beilstein J. Org. Chem. 2024, 20, 25–31, doi:10.3762/bjoc.20.4

• and zero-filling are now applied automatically by common software packages using presets. While this provides convenience, it also leads to a loss of knowledge for new users on their impact on properties such as resolution and signal-to-noise ratio and the balance between them. For teaching labs

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• effect on the yield of the final compounds 3 observed. The structures of compounds 3a–u were confirmed by IR, 1H and 13C NMR spectroscopy (Figures S1‒S44 in Supporting Information File 1) as well as by high-resolution mass spectrometry (HRMS). X-ray data obtained for compound 3g gave us final proof of

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• result indicated that CmaG is a component of Cma PKS. From NMR analysis and high-resolution (HR)MS analysis ([M + H]+ ion at m/z = 222.0766, which corresponds to C11H12NO4+, calcd. 222.0761) of purified 6, the structure of 6 was determined as N-acetyl-3-aminocoumaric acid (Figures S9–S13 and Table S1 in

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• certain time intervals within 2 hours and examined by ESI LC–MS. Throughout the high-resolution electrospray-ionization time-of-flight (HRESI–TOF) mass analysis of the reaction mixture at 0 °C, the following peaks were observed: m/z = 246.0366 ([M + H]+ calcd for C11H5F5N, 246.0337), m/z = 857.1468 ([M

• predominately observed (Figure S48 in Supporting Information File 1). According to high-resolution electrospray-ionization time-of-flight (HRESI–TOF) analysis, at the beginning of the reaction, mass peaks of intermediates II and IV arose as a result of tripyrrane 1 addition to N-tosylimine 2d. Further

• aryl-bearing N-tosylimines, but a 4-(CF3)C6H4 group led only to the formation of porphyrin compounds. A mechanistic perspective for the formation of porphyrinic products was acquired via a set of high-resolution mass analyses of selected model reactions. The results indicated that azafulvene-ended

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• ), thus providing valuable additional isomer resolution [4]. We demonstrated that this multidimensional MS–IR molecular fingerprint is unique to each carbohydrate building block and can be used to resolve their full sequence, including their monosaccharide content and the detail of their linkages

• a change in binning. To take this into account, data were binned with downgraded resolution then re-binned with 1 cm−1 step. The down sampling factor was randomly picked in a range from 1 to 5. Small variations of the calibration of the laser wavenumber may occur from day to day, leading to a shift

• a maximum accuracy variation of 0.5%. We demonstrated that the neural network is suitable for MS–IR classification in experimental conditions with variable resolution, noise or energy jitter. The question remains on how to discriminate unknown molecules or to identify problematic spectra, such as

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• on a Bruker 300 Avance spectrometer (at 300 and 75.5 MHz for the 1H and 13C spectra, respectively) or on a Bruker Avance III HD (at 600 MHz for 1H and at 150 MHz for 13C spectra) at specified temperatures. High-resolution MS was measured on a Bruker MicroTOF II instrument using positive electrospray

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• several synthetic challenges that require further investigation and resolution: First, the current reliance on redox-active esters as radical precursors in iodide/phosphine-mediated conversions restricts the potential applications of these conversions in synthesis. Therefore, it is highly recommended to

Active-metal template clipping synthesis of novel [2]rotaxanes

• Cătălin C. Anghel,
• Teodor A. Cucuiet,
• Niculina D. Hădade and
• Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

• ) relative to the residual solvent peak. High-resolution mass spectra were recorded on a ThermoScientific (LTQ XL, Orbitrap) spectrometer, in positive ion mode, using Electrospray or APCI techniques. Experimental procedures and characterization of compounds Compound 2: In a round-bottom flask compound 1

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• high-resolution mass spectrometry (ESI), where it was shown the fragment corresponding to complex 1 that lost one isothiocyanate, [M − NCS]+, as the primary signal. Elemental analysis matched the calculated values, incorporating an additional MeOH molecule. Recrystallization was afforded by re

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• -standard approach [44] (see the Supporting Information File 1 for details). The high-resolution mass spectrum (ESI+) of a mixture of 5 and the impurity, in addition to a peak at m/z = 329.1696 [M + H]+ for compound 5, shows a peak at m/z = 319.1862 [M + H]+, consistent with the molecular formula of

• structure (see Supporting Information File 1). The high-resolution mass spectrum (ESI+) confirmed its chemical formula as C12H16N12. Thus, we found that, in contrast to the reported data [40], the reaction between imidate 4 and hydrazine hydrate (4 equiv) in refluxing EtOH for 2 h afforded macrocycle 5 in a

• decoupling, DEPT-135 experiments as well as HMQC, HMBC, and NOESY correlation techniques were used to aid in the assignment of 1H and 13C NMR signals. Elemental analyses (CHN) were performed using a Thermo Finnigan Flash EA1112 apparatus. High-resolution mass spectra (HRMS) were obtained using a Bruker

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• )diboron catalyzed by Pd(dpf)Cl2/KOAc. Finally, TPECNz was obtained as red solid in a reasonable yield by a Suzuki-type cross-coupling reaction between 3 and 4,9-dibromonaphtho[2,3-c][1,2,5]thiadiazole. The chemical structure and purity of compound 3 were verified by 1H NMR, 13C NMR, and high-resolution

• purchased from commercial resources and used without further purification. 1H NMR and 13C NMR spectra were recorded with a Bruker AVANCE III HD 600 (600 MHz for 1H and 151 MHz for 13C) using CDCl3 as a solvent containing TMS as an internal standard. High-resolution mass spectrometry (HRMS) analysis was

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

• Aaron H. Shoemaker,
• Elizabeth A. Foker,
• Elena P. Uttaro,
• Sarah K. Beitel and
• Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

• (Colby College) and Prof. Bruce Foxman (Brandeis University) for X-ray analysis of compound 8. High-resolution mass spectra were obtained at the Mass Spectrometry Lab at the University of Illinois. Funding We thank the donors of the American Chemical Society Petroleum Research Fund (Grant No. 59202-UNI1

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• disticha. The structures of compounds 1–7 were elucidated by extensive 1D and 2D NMR spectroscopic analyses, including 1D total correlation spectroscopy (TOCSY), HSQC, HMBC, double quantum-filtered (DQF)-COSY, heteronuclear two-bond correlation (H2BC), and HSQC-TOCSY experiments, as well as high-resolution

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• soluble upon radiation, respectively. Some early negative photoresists undergo a photochemical crosslinking process of 1,3-diene cyclic polymers [190] (cf. section 3.2), but such systems are no longer studied due to the poor resolution and sensitivity. On the other hand, positive resists based on

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• cameroonensis, isolated from the root of Trema guineensis, a Cameroonian medicinal plant from the family Ulmaceae [11]. Results Structural elucidation Diaporthe cameroonensis, which showed an interesting high-performance liquid chromatography–diode array detector–high-resolution mass spectrometry (HPLC–DAD–HRMS

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• deprotonation the latter with sodium hydride base. The compound shows poor solubility in most common organic solvents with moderate solubility in dichloromethane, 1,2-dichlorobenzene and dimethyl sulfoxide (DMSO). Compound 4BGIPN was characterized by high-resolution mass spectrometry (HRMS), elemental analysis

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• . Acknowledgements The authors are grateful to the USIC, University of Delhi, Delhi, India for providing the NMR and high-resolution mass data. Funding MN is thankful to IoE, University of Delhi, India for providing a FRP grant. CT and PS are thankful to UGC, New Delhi, India for the award of Senior Research

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• -diaminopyrazoles 4a–c (Scheme 2). The structures of compounds 4a–c were confirmed by 1H and 13C NMR spectroscopy data, as well as high-resolution mass spectrometry (HRMS). Compound 4a was previously obtained by another method [18]. The spectral characteristics of diaminopyrazole 4a reported in [18] correspond to