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

• (practical laboratory classes including examples of synthesis and compound characterization), NMRium provides a full 1D FT workflow and therefore an ideal possibility to introduce basic concepts of data processing, data presentation, and data evaluation. Spectra from most NMR instruments may be directly used

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

• embryo kidney cells (HEK-293), glioblastoma (A-172), and osteosarcoma (HOS) cells. Supporting Information Supporting Information File 25: Full experimental details and characterization data of all new compounds. Supporting Information File 26: Copies of NMR spectra of all new compounds. Funding Design

Long oligodeoxynucleotides: chemical synthesis, isolation via catching-by-polymerization, verification via sequencing, and gene expression demonstration

• Yipeng Yin,
• Reed Arneson,
• Alexander Apostle,
• Adikari M. D. N. Eriyagama,
• Komal Chillar,
• Emma Burke,
• Martina Jahfetson,
• Yinan Yuan and
• Shiyue Fang

Beilstein J. Org. Chem. 2023, 19, 1957–1965, doi:10.3762/bjoc.19.146

• ], direct evidence is lacking in the literature. For the CBP method to be practically useful, we believe that characterization of the ODNs via DNA sequencing is imperative. Based on this reasoning, ODNs from three colonies originated from the 399 nt GFP gene fragment were sequenced (see Supporting

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• , for other compounds α-bromo-N-tosylhydrazone was used. Yields refer to isolated compounds. Proposed reaction mechanism. Gram-scale synthesis of compound 7c. Optimizing the reaction conditions.a Supporting Information Supporting Information File 22: Characterization data and 1H, 13C NMR, and HRMS

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• sieves (4 Å). Dichloromethane (Aldrich), methanol (Merck), and sodium carbonate (Merck) were used as received. Compounds 2–6 were synthesized following our previous reports [20][21][22][23][44][45][46][47]. The characterization data of 7 and 8 are compatible with the published data in ref. [23

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

• beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation

• [12], and drug delivery [13]. In spite of the important advancements in this field, the synthesis and characterization of these fascinating, complex molecules remains an important challenge and often requires intricate synthetic approaches. After the first templated synthesis of a [2]catenane

• envisaged to combine active-metal template and clipping strategies and we report herein the synthesis and characterization of novel [2]rotaxanes by this new method that we name active-metal template clipping (Figure 1b). Thus, our approach involves the use of a metal ion connected to the dumbbell-shaped

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

• maintaining high selectivity for carbon products. Results and Discussion Synthesis and characterization of the new Co(II)-based catalyst The novel cobalt(II) complex 1 was synthesized in dry methanol (MeOH) by mixing in a 2:1 ratio, the chelating diimine ligand, 1-benzyl-4-(quinolin-2-yl)-1H-1,2,3-triazole

• detect, if the two polymorphs show different catalytic activity, as in the following investigations the amorphic powder was used. Spectroscopic and electrochemical characterization The Co(II) complex 1 was characterized by UV–vis absorption spectroscopy in N,N-dimethylacetamide (DMA), as it was the

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• errors of 2% (hdz-CH3) and 0% (hdz-NO2). In general, the structures calculated involving the IEFPCM formalism (water phase) displayed the best agreement with the experimental data. Regarding the vibrational characterization, infrared spectra were also calculated with both B3LYP/6-311G(d,p) – gas phase

• and hdz-NO2 (Figure 5A and 5B, respectively). 13C NMR and 2D homonuclear (COSY) and heteronuclear (13C,1H-HSQC and HMBC) experiments were employed for the full characterization of these hydrazones, and the spectra can be seen in Supporting Information File 1, Figures S5–S12. Both compounds exhibit

• maintained in DMSO-d6 solution. It is worth noting that the presence of the electron-withdrawing nitro substituent in hdz-NO2 makes the interaction stronger. An IR spectroscopy study, which was supported by computational calculations, as well as a complete NMR characterization of both compounds, align with

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

• Frontier Research Center, Vidyasirimedhi Institute of Science and Technology, Wangchan, Rayong 21210, Thailand 10.3762/bjoc.19.122 Abstract Herein, we report the synthesis and characterization of an efficient ambipolar charge-carrier-transporting deep-red fluorophore (TPECNz) based on a donor–acceptor

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• NMR spectroscopy, mass spectrometry, and elemental analysis. See Supporting Information File 1 for full synthetic and characterization details. Optical properties Using UV–visible spectroscopy, the optical properties for PDIN-FB, PDIN-B, CN-PDIN-FB, and CN-PDIN-FB in both solution and film form were

• no barriers between the active layer and the CIL interface, indicating efficient charge extractions. In addition, to further confirm the charge extraction and recombination, the PAIOS (platform for all-in-one characterization of solar cells) tool from Fluxim was used to measure transient photocurrent

• investigation of the processes involved in the formation of the interfacial layer between the donor–acceptor and the charge transport layer. Nevertheless, based on all the optoelectrical characterization, proposed N-annulated perylene diimides-based CILs are suitable candidates for CILs that can be replaced

Lewis acid-promoted direct synthesis of isoxazole derivatives

• Dengxu Qiu,
• Chenhui Jiang,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

• of reaction conditions for the synthesis of isoxazolesa. Supporting Information Supporting Information File 6: Characterization data and copies of spectra. Funding We are grateful for the financial support from the China Postdoctoral Science Foundation (2018T110533), the Natural Science Foundation

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

• chemical constituents of another new species of Diaporthe. This genus contains many plant pathogenic, endophytic, and saprobic species [7]. So far, the investigations of chemical constituents of Diaporthe species, have led to the isolation and characterization of a myriad of potent natural products with

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

• Tzu-Yu Huang,
• Mario Djugovski,
• Sweta Adhikari,
• Destinee L. Manning and
• Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

• was run in the absence of azide using optimized conditions (see Supporting Information File 1, mechanistic study, section 8). However, its further characterization was not possible because it disappeared upon workup. Finally, a 2D NOESY experiment was utilized to confirm the regiochemistry of 4-(1-(4

• . Proposed mechanism. Scale-up experiment. Optimization of reaction conditions.a Supporting Information Supporting Information File 2: General information, experimental procedures for all the substrates and intermediates, characterization data, and NMR spectra (1H, 19F, and 13C NMR). Funding Research

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• potential of those solvents in many applications (electrodeposition, organic syntheses, biomass extraction, etc.) [11][12]. The more recent ones also deal with the importance of a better characterization of DES [13] and a clear evaluation of their sustainability via life-cycle assessment to evaluate the

• Information Supporting Information File 96: Experimental procedures, characterization of compounds, copies of NMR spectra and HRMS spectra. Acknowledgements The author acknowledges the NMR platform of the University of Lorraine, especially Sandrine Rup-Jacques and the MassLor platform, especially Jasmine

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• –B14 as tested against 12 unique microbial species. Zones of inhibition of chelerythrine variants C1–C4 compared to chelerythrine (C). Supporting Information Supporting Information File 106: Synthetic procedures, characterization, methods for biological testing, and copies of NMR spectra of new

Cyclization of 1-aryl-4,4,4-trichlorobut-2-en-1-ones into 3-trichloromethylindan-1-ones in triflic acid

• Vladislav A. Sokolov,
• Andrei A. Golushko,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2023, 19, 1460–1470, doi:10.3762/bjoc.19.105

• . Selected calculated (DFT) electronic characteristics of the protonated forms Aa, Ba, Ca, and Da generated from hydroxy ketone 1a and enone 2a, and values of Gibbs energies of reactions (ΔG, kJ/mol). Supporting Information Supporting Information File 170: Experimental, characterization data and copies of

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

• Angel Palillero-Cisneros,
• Paola G. Gordillo-Guerra,
• Fernando García-Alvarez,
• Olivier Jackowski,
• Franck Ferreira,
• Fabrice Chemla,
• Joel L. Terán and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

• –H bonds.a Optimization of the air-promoted 1,4-addition of dialkylzinc reagents onto N-(tert-butanesulfinyl) α-(aminomethyl)acrylates. Supporting Information Supporting Information File 94: General information, characterization data, chemical correlation, and copies of NMR spectra

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

• Hans-Ulrich Reissig and
• Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

• . Supporting Information Supporting Information File 86: Experimental procedures, spectroscopic and analytical characterization data of new compounds as well as copies of the NMR spectra. Acknowledgements We thank Dr. Reinhold Zimmer for his valuable assistance during preparation of the manuscript. Funding We

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

• Feng Chen,
• Xiu-Hua Xu,
• Zeng-Hao Chen,
• Yue Chen and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

• Supporting Information File 188: Experimental procedures, product characterization, and copies of NMR spectra. Funding National Natural Science Foundation of China (21991121), National Key Research and Development Program of China (2021YFF0701700), Natural Science Foundation of Shandong Province

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

• Olfa Mhasni,
• Jalloul Bouajila and
• Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

• ) onto acyclic MBH alcohols 1a–f. Supporting Information Supporting Information File 69: Full experimental details and characterization data of all new compounds. Supporting Information File 70: 1H and 13C NMR and HRMS spectra of compounds. Acknowledgements We thank the Tunisian Chemical Society for

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• ://www.ccdc.cam.ac.uk). Supporting Information File 138: Characterization data, 1H NMR, 13C NMR, and HRMS spectra of the compounds. Funding This work was financially supported by the National Natural Science Foundation of China (Nos. 21871227).

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

• ]chromeno[2,3-h]quinoxalinoporphyrin 3. Optimization of the reaction conditions for the synthesis of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrin 3.a Supporting Information Supporting Information File 186: Characterization data, 1H and 13C NMR spectra of newly prepared porphyrin products

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

• Supporting Information File 131: Full experimental details and characterization data of all new compounds. Supporting Information File 132: Copies of NMR spectra of all new compounds. Funding The authors thank the Russian Science Foundation (project 23-13-00248).

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• Information Supporting Information File 124: Experimental procedures, characterization data, and 1H and 13C NMR spectra for all new compounds. Funding This work was supported by the Russian Science Foundation (grant No. 22-13-00356).

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

• Damiano Diprima,
• Hannes Gemoets,
• Stefano Bonciolini and
• Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

• the addition of 1 equivalent of aromatic molecules to the standard solution using tetrahydrothiophene as the substrate. Supporting Information Supporting Information File 104: General procedures, product characterization, and copies of 1H NMR and 13C NMR spectra of compounds. Funding We are grateful