New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• for 35Cl and 37Cl isotopes, respectively, with an approximately 3/4 and 1/4 proportion. The symmetry of the obtained compound TP1 gives simple NMR spectra, with the 31P NMR spectrum showing a singlet signal (Figure 2) and the signal at 169.5 ppm, on the 13C NMR spectrum, confirming the presence of a

• %). No isotope peaks were observed at the MS of the compound, in agreement with the full displacement of the chlorine atoms. The NMR spectra (Figure 3) presented a similar pattern of the corresponding 4-amino derivative TP1. The 31P NMR spectrum shows only one singlet in accordance with the symmetry of

• triazinephosphonate compounds. Partial view of 1H and 31P NMR spectra of 4-aminophenyltriazinephosphonate derivatives TP1–TP3. Partial view of 1H and 31P NMR spectra of (4-hydroxyphenyl)triazinephosphonate derivatives TP4–TP6. Preparation of the new doped membranes. Comparison of in-plane proton conductivity vs RH of

Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction

• Evgen V. Govor,
• Vasyl Naumchyk,
• Ihor Nestorak,
• Dmytro S. Radchenko,
• Dmytro Dudenko,
• Yurii S. Moroz,
• Olexiy D. Kachkovsky and
• Oleksandr O. Grygorenko

Beilstein J. Org. Chem. 2024, 20, 1604–1613, doi:10.3762/bjoc.20.143

• synthesis of compound library 4, experimental section including compound characterization data, and copies of NMR spectra. Supporting Information File 13: Structures of reactants 1, 2, and 3. Supporting Information File 14: Parallel synthesis of compound library 4. Supporting Information File 15

• : Experimental part. Supporting Information File 16: Copies of NMR spectra. Acknowledgements Dedicated to the memory of Kyrylo Burmagin and Yaroslav Mayboroda, students of Chemical Faculty at Taras Shevchenko National University of Kyiv, trainees at Enamine, and volunteer soldiers who died defending their

Mining raw plant transcriptomic data for new cyclopeptide alkaloids

• Draco Kriger,
• Michael A. Pasquale,
• Brigitte G. Ampolini and
• Jonathan R. Chekan

Beilstein J. Org. Chem. 2024, 20, 1548–1559, doi:10.3762/bjoc.20.138

• products from A. bettizickiana observed by LC–MS/MS. Supporting Information The sequencing data used in this study is openly available in the NCBI SRA. Supporting Information File 9: Additional details and figures including NMR spectra and MS/MS fragmentation. Supporting Information File 10: Specific

Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

• Pooja Goyal,
• Akhil K. Dubey,
• Raghunath Chowdhury and
• Amey Wadawale

Beilstein J. Org. Chem. 2024, 20, 1518–1526, doi:10.3762/bjoc.20.136

• ent-3aa-ent-3na, 1H, 13C NMR spectra of 3aa–na, 1H NMR of ent-3aa–ent-3na and their HPLC traces and single crystal data of ent-3ba. Acknowledgements The authors are thankful to Ms. Ketki Lele for her help in some preliminary experiments. Funding The authors thank the Department of Atomic Energy (DAE

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

• Christopher Mairhofer,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

• pronucleophile, followed by a phase-transfer-catalyzed nucleophilic substitution by the azide. Furthermore, we also obtained a first proof-of-concept for the conceptually analogous α-nitration by using NaNO2 under otherwise identical conditions. Experimental General details 1H, 13C and 19F NMR spectra were

• Research Center “RERI uasb”. All NMR spectra were referenced on the solvent residual peak (CDCl3: δ = 7.26 ppm for 1H NMR, δ = 77.16 ppm for 13C NMR,19F NMR unreferenced). IR spectra were recorded on a Bruker Alpha II FTIR spectrometer with diamond ATR-module using the OPUS software package. HRMS spectra

• details and copies of NMR spectra. Acknowledgements We are grateful to Prof. Dr. Himmelsbach (Institute of Analytical Chemistry, JKU Linz) for support with HRMS analysis and Anna-Malin Draxler (Institute of Org. Chemistry, JKU Linz) for experimental support. Funding The used NMR spectrometers were

Towards an asymmetric β-selective addition of azlactones to allenoates

• Behzad Nasiri,
• Ghaffar Pasdar,
• Paul Zebrowski,
• Katharina Röser,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

• giving access to the acyclic α-amino acid-based amides 6 straightforwardly. Experimental General details 1H and 13C NMR spectra were recorded on a Bruker Avance III 300 MHz spectrometer with a broad band observe probe. All NMR spectra were referenced on the solvent residual peak (CDCl3: δ 7.26 ppm for 1H

• to allenoate 3aa. Supporting Information Supporting Information File 20: Full experimental and analytical details and copies of NMR spectra and HPLC traces. Acknowledgements We are grateful to Prof. Dr. Himmelsbach (Institute of Analytical Chemistry, JKU Linz) for support with HRMS analysis

Electrophotochemical metal-catalyzed synthesis of alkylnitriles from simple aliphatic carboxylic acids

• Yukang Wang,
• Yan Yao and
• Niankai Fu

Beilstein J. Org. Chem. 2024, 20, 1497–1503, doi:10.3762/bjoc.20.133

• catalytic cycles. Reaction discovery and optimization.a Supporting Information Supporting Information File 18: Experimental procedures, mechanistic studies, analytical data and copies of NMR spectra. Funding We thank the National Natural Science Foundation of China (No. 22071252) and the Chinese Academy

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• silica gel (60 Å pore size, 40–63 µm). 1H and 13C NMR spectra were recorded on a JEOL ECS-400 spectrometer or on Bruker Avance 300 and 400 spectrometers. Structural assignments were made with additional information from gCOSY, HMBC, and gHMQC experiments. High-resolution mass spectra (HRMS) were

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• Information Supporting Information File 6: Experimental procedures, characterization data, and copies of NMR spectra of all new compounds. Funding This research was founded by the National Natural Science Foundation of China (22161051, 21302163) and Yunnan XingDian Youth Talent Support Program (XDYC-QNRC

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

• Xiu-Yu Chen,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

• ). The reaction in toluene, methylene dichloride or acetonitrile at room temperature afforded an unexpected tricyclic compound 4a in 12–18% yields (Table 1, entries 4–6). 1H NMR spectra clearly indicated that two molecules of dimethyl but-2-ynedioates took part in the reaction. The yields of the product

• clearly showed that this reaction has a wide scope of substrates. The obtained compounds 4a–t have four chiral carbon atoms. The multicomponent reaction might result in several diastereomers. On the basis of TLC analysis and 1H NMR spectra of the crude products, only one relative stereochemistry was

• that all tricyclic compounds have this kind of relative configuration on the basis of NMR spectra and single crystal structure. In order to develop the scope of the reaction, another kind of 5,6-unsubstituted 1,4-dihydropyridines 5 were also employed in the reaction, which were previously prepared from

Challenge N- versus O-six-membered annulation: FeCl₃-catalyzed synthesis of heterocyclic N,O-aminals

• Giacomo Mari,
• Lucia De Crescentini,
• Gianfranco Favi,
• Fabio Mantellini,
• Diego Olivieri and
• Stefania Santeusanio

Beilstein J. Org. Chem. 2024, 20, 1412–1420, doi:10.3762/bjoc.20.123

• formation of N,O-aminals 5 and hemiaminals 6. Control mechanistic experiments. Optimization conditions for the Lewis acid-catalyzed intramolecular cyclization of 4a. Supporting Information Supporting Information File 16: General experimental information, synthetic procedures, analytical data and NMR

• spectra for the reported compounds. Acknowledgements The authors thank Dr. Anna Maria Gioacchini and Prof. Michele Menotta who competently performed the mass spectra.

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

• Simone Gräßle,
• Laura Holzhauer,
• Nicolai Wippert,
• Olaf Fuhr,
• Martin Nieger,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

• were submitted to the repository chemotion (https://www.chemotion-repository.net/). All DOIs minted for the data are linked in Supporting Information File 1 and the NMR spectra are given in Supporting Information File 2. Information on the availability of the data and the physical material of the

• /data_request/cif. Supporting Information File 8: Experimental part. Supporting Information File 9: NMR spectra. Supporting Information File 10: Information on the availability of the data and the physical material of the target compounds. Acknowledgements We thank Jana Barylko for synthetic assistance

Rhodium-catalyzed homo-coupling reaction of aryl Grignard reagents and its application for the synthesis of an integrin inhibitor

• Kazuyuki Sato,
• Satoki Teranishi,
• Atsushi Sakaue,
• Yukiko Karuo,
• Atsushi Tarui,
• Kentaro Kawai,
• Hiroyuki Takeda,
• Tatsuo Kinashi and
• Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 1341–1347, doi:10.3762/bjoc.20.118

• Information Supporting Information File 98: General procedures and analytical data, including copies of 1H NMR and 13C NMR spectra. Acknowledgements We would like to thank Dr. Antal Harsányi at Euroapi Hungary for his helpful comments to improve the quality of the article.

Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

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

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

• File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, spectra of all new compounds, and X-ray crystallographic data. Acknowledgements The crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic

Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation

• Kosuke Yamamoto,
• Kazuhisa Arita,
• Masami Kuriyama and
• Osamu Onomura

Beilstein J. Org. Chem. 2024, 20, 1327–1333, doi:10.3762/bjoc.20.116

• Supporting Information Supporting Information File 94: Experimental procedures, characterization data, and copies of NMR spectra of the products. Acknowledgements The spectral data were collected with the research equipment shared in the MEXT Project for promoting public utilization of advanced research

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

• Ayhan Yıldırım

Beilstein J. Org. Chem. 2024, 20, 1308–1319, doi:10.3762/bjoc.20.114

• the bis structure are in equilibrium with maleamic acid precursors (Scheme 3) complicates the interpretation of their 1H and 13C NMR spectra. The existence of these precursors is clearly demonstrated by both their 1H and 13C NMR spectra (Supporting Information File 1). It should be noted that in the

• case of compound 2p, unlike the other two compounds, the equilibrium is largely in favor of the product of interest and the NMR spectra confirm this. From the mechanistic point of view of the IMDAF reaction, the presence of both s-cis and s-trans conformations of maleamic acid intermediates in the

• in Flawil, Switzerland). The IR spectra were measured by Spectrum Two FT-IR spectrometer (PerkinElmer, Massachusetts, USA). The NMR spectra were measured using Bruker Ultrashield Plus Biospin 400 MHz NMR spectrometer and A600a Agilent DD2 600 MHz NMR spectrometer (Santa Clara, California, USA) and

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• measurements and analyzed with mMass [29] software. 1H and 13C NMR spectra were recorded on JNM-ECS 400 spectrometer using the sample solutions in chloroform-d (CDCl3). Raman spectra were recorded on LabRam HR800 (Horiba Ltd.) and take the average of more than ten different spots for the final curve. UV–Vis

• , rt, 1.5 h; iv) p-chloranil, dichloromethane, rt, 5 h. Supporting Information Supporting Information File 86: Details of theoretical calculations, experimental procedures, copies of 1H and 13C NMR spectra. Acknowledgements Computation time was provided by supercomputer system, Academic Center for

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• monoselenides 1 and 2, respectively. The signal at 371 ppm corresponded to compound 1, based on a previous report [47]. In turn, the other signal was assigned to the isomeric compound 2. A similar observation was made in the 77Se NMR spectra of the pure diaryl diselenide isomers obtained from the reaction of

• ]. The mass spectra of purified compounds 11 and 12 showed peaks for [M + H]+ (Figures S21 and S26, Supporting Information File 1). The 77Se NMR spectra of the purified isomers 11 and 12 showed resonance signals at 300 and 394 ppm, respectively (Figures S24 and S29, Supporting Information File 1

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

• Carolina S. Marques,
• Aday González-Bakker and
• José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

• -acetamide carboxamide isatin hybrids 8 easy accessed via deprotection reaction on the Ugi-adducts 5 and 7. TFA: trifluoroacetic acid. Supporting Information Supporting Information File 56: Experimental procedures, analytical data, NMR spectra and biological assays. Funding C. S. M. thanks the Norma

Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

• Manoel T. Rodrigues Jr.,
• Aline S. B. de Oliveira,
• Ralph C. Gomes,
• Amanda Soares Hirata,
• Lucas A. Zeoly,
• Hugo Santos,
• João Arantes,
• Catarina Sofia Mateus Reis-Silva,
• João Agostinho Machado-Neto,
• Leticia Veras Costa-Lotufo and
• Fernando Coelho

Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99

• reactivity of 9dc,dl. Supporting Information Supporting Information File 26: Experimental section and copies of 1H and 13C NMR spectra of all new compounds. Funding The authors thank the São Paulo Foundation Science (FAPESP, #2018/02611-0, #2013/07600-3 and #2023/18007-3, to FC) for financial support. F. C

Kinetically stabilized 1,3-diarylisobenzofurans and the possibility of preparing large, persistent isoacenofurans with unusually small HOMO–LUMO gaps

• Qian Liu and
• Glen P. Miller

Beilstein J. Org. Chem. 2024, 20, 1099–1110, doi:10.3762/bjoc.20.97

• modified cardboard box were utilized for detection of TLC spots. Melting points were determined in open capillary tubes using a Mel-Temp apparatus, and are uncorrected. Proton nuclear magnetic resonance (1H NMR) spectra and carbon nuclear magnetic resonance (13C NMR) spectra were recorded on either a

• -dimesityl-1,4-dihydro-1,4-epoxynaphthalene-2,3-dicarboxylate (27). Supporting Information Supporting Information File 24: 1H NMR stability studies for compounds 3 and 23, 1H and 13C NMR spectra for key compounds and ESI high-resolution mass spectra. Funding The authors gratefully acknowledge financial

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• building blocks for polymer and materials chemists, offering improved sustainability compared to standard methodologies. Experimental General Solvents and reagents were commercial grade and used as received. 1H NMR spectra were acquired with a Bruker Avance 400 spectrometer (Billerica, MA, USA). The

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

• Vladislav V. Nikol’skiy,
• Mikhail E. Minyaev,
• Maxim A. Bastrakov and
• Alexey M. Starosotnikov

Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94

• . Yields of compounds 12 and 13. Supporting Information Supporting Information File 16: Experimental section, NMR spectra and X-ray analysis data.

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• , 230−400 mesh from Whatman. Routine 300(75) MHz 1H(13C) NMR spectra were recorded on Varian Mercury 300 or Gemini 300 spectrometers. Routine 500(125) MHz 1H(13C) NMR were recorded on an INOVA 500 spectrometer. 2D NMR spectra were recorded using a 600 MHz Varian instrument. Chemical shifts (δ) are given

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• details and copies of 1H, 13C, and 19F NMR spectra. Acknowledgements T.D. thanks for the generous gift of fluoroalcohols from Central Glass Co., Ltd. Funding N.T. and T.D. acknowledge support from JSPS KAKENHI Grant Number 20K06980 (N.T.) and 19K05466 (T.D.), JST CREST grant number JPMJCR20R1 (T.D.), and