Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids

• Luan A. Martinho,
• Victor H. J. G. Praciano,
• Guilherme D. R. Matos,
• Claudia C. Gatto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2025, 21, 2618–2636, doi:10.3762/bjoc.21.203

• crystal XRD analysis confirmed the presence of the expected products and the stereochemistry of the newly created olefinic compound as being Z, as expected. Compound 3n crystallizes in the monoclinic crystal system with four molecules in the asymmetric unit whereas 4n crystallizes in the triclinic crystal

Thiadiazino-indole, thiadiazino-carbazole and benzothiadiazino-carbazole dioxides: synthesis, physicochemical and early ADME characterization of representatives of new tri-, tetra- and pentacyclic ring systems and their intermediates

• Gyöngyvér Pusztai,
• László Poszávácz,
• Anna Vincze,
• András Marton,
• Ahmed Qasim Abdulhussein,
• Judit Halász,
• András Dancsó,
• Gyula Simig,
• György Tibor Balogh and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2220–2233, doi:10.3762/bjoc.21.169

• F254 and by UHPLC–MS on a Shimadzu LC-40 UHPLC equipment equipped with a quaternary pump, degasser, autosampler, column oven, diode array detector, and an LCMS-2020 quadrupole mass spectrometer. Single-crystal X-ray diffraction (SC-XRD) measurements were carried out on a Rigaku R-Axis Spider

Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines

• Margherita Gazzotti,
• Fabrizio Medici,
• Valerio Chiroli,
• Laura Raimondi,
• Sergio Rossi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147

• product was unambiguously determined, by XRD analysis, to be (2S,3S,4aR,8aR)-2b as shown in Figure 1. Following the promising results obtained from the batch approach, the electroreductive coupling was investigated under continuous flow conditions [48][49][50], with the aim to improve process efficiency

Calcium waste as a catalyst in the transesterification for demanding esters: scalability perspective

• Anton N. Potorochenko and
• Konstantin S. Rodygin

Beilstein J. Org. Chem. 2025, 21, 1520–1527, doi:10.3762/bjoc.21.114

• acetylene production, was investigated. The catalyst was obtained by calcination of calcium carbide slag at 600 °C (CS600) and characterized by XRD and FTIR analysis. The transesterification reactions were carried out with primary alcohols, producing fatty acid alkyl esters in 51–99% yields, depending on

• was calcined at 600 °C before use and the catalyst CS600 was characterized using XRD and FTIR analysis, confirming the presence of CaO as the main phase. The primary alcohols successfully reacted in the transesterification reaction to give the corresponding fatty acid alkyl ester mixtures in yields

• CS600 catalyst was analyzed by XRD and FTIR analysis and the results were consistent with our published work [72]. The main phase was CaO (Figure 1) with reflections at 2θ = 32.2, 37.3, 53.8, 64.1, 67.4, 79.6, 88.5 (XRD and FTIR data is given in Supporting Information File 1). The catalyst CS600 was

Synthetic approach to borrelidin fragments: focus on key intermediates

• Yudhi Dwi Kurniawan,
• Zetryana Puteri Tachrim,
• Teni Ernawati,
• Faris Hermawan,
• Ima Nurasiyah and
• Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

• LiAlH4 in ether to form alcohol 40 (89%) (Scheme 3). The primary alcohol 40 was then converted to its iodide derivative 42 (89%), from which single crystals were obtained, and its structure was determined unequivocally by XRD crystallography. Iodide 42 was then reacted with sodium phenylsulfinate in DMF

• 94% yield. Like 40, iodination of ent-40 gave crystalline product ent-42, and its structure was confirmed by XRD crystallography. The intermediate ent-40 was then subjected to the same tosylation/thiolation/oxidation sequence used for the 40 to 41 conversion, yielding ent-41 in comparable yield (82

• simple impurity removal from the key chiral intermediates through recrystallization, from which their exact structures could be elucidated by XRD crystallography. Zhou’s approach for constructing Omura’s C3–C11 fragment In 2018, Zhou and co-workers developed an efficient, high-yielding iterative

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

• Krishna Pandey,
• Lucas X. Orton,
• Grayson Venus,
• Waseem A. Hussain,
• Toby Woods,
• Lichang Wang and
• Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

• Information File 1. Single crystals with quality suitable for XRD analysis were obtained in both cases (Figure 5). Unlike the previous assumption of metal coordination at the macrocycle core [17], the crystal structures reveal complexation of both cations at the periphery of the macrocycle. Both 1/LiBArF20

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

• 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

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

• and DFT quantum chemical calculations for 7a, 7b, 8a and 8b. Supporting Information File 14: Crystallographic information file for compound 7b. Acknowledgements XRD studies were performed in accordance with the State Task, State registration № 124013100858-3 (V. V. Tkachev, G. V. Shilov, S. M

Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF₅- and CF₃SF₄-containing [2]staffanes

• Jón Atiba Buldt,
• Wang-Yeuk Kong,
• Yannick Kraemer,
• Masiel M. Belsuzarri,
• Ansh Hiten Patel,
• James C. Fettinger,
• Dean J. Tantillo and
• Cody Ross Pitts

Beilstein J. Org. Chem. 2024, 20, 3134–3143, doi:10.3762/bjoc.20.259

• truncated after incorporation of two bicyclopentane (BCP) units. Synthetic and computational studies suggest this phenomenon can be attributed to alternating radical polarity matching. In addition, single-crystal X-ray diffraction (SC-XRD) data reveal structurally interesting features of the CF3SF4

• bicyclopentyl radical philicities. In addition, we demonstrate that similar reaction conditions can be applied to the synthesis of the analogous CF3SF4-containing [2]staffane (CF3SF4-BCP-BCP-Cl, 3). Finally, we examined compound 3 by SC-XRD and found that it undergoes a phase transition as a function of rate of

• for the first time created an opportunity for structural analysis. We previously reported and contextualized single-crystal X-ray diffraction (SC-XRD) data on 2 [36]; thus, we proceeded to grow crystals of 3 suitable for X-ray analysis through slow evaporation of ethyl acetate. To our surprise, an

Structure and thermal stability of phosphorus-iodonium ylids

• Andrew Greener,
• Stephen P. Argent,
• Coby J. Clarke and
• Miriam L. O’Duill

Beilstein J. Org. Chem. 2024, 20, 2931–2939, doi:10.3762/bjoc.20.245

• ][26][27] and the mechanisms by which they decompose when heated through a systematic investigation of structural data from X-ray diffraction (XRD) and thermal stability data from differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The insights from this study will galvanise

• the rational design and synthesis of novel, unstabilised hypervalent iodine(III) compounds and expand the application of these powerful reagents in organic synthesis. Results and Discussion Structural data Twelve phosphorus-iodonium ylids were synthesised (Figure 2). X-ray diffraction data (XRD) of

• compounds 1a–f and 1i were measured (see Supporting Information File 2), and data for compounds 2–4 were sourced from the literature [24][26][28]. A representative set of structural parameters obtained from XRD is presented in Table 1. All compounds show a trigonal bipyramidal structure, in which the 3

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• substitution at the 4-position of benzofuranone hindered the reaction, leading to a very poor yield of the desired benzophenone product. Further, to confirm the structure and the substitution pattern in the 2-hydroxybenzophenones, single crystal XRD data were collected for the representative compounds 4ja, 4fb

• -crystal XRD The data were collected using a similar method as reported by us earlier [23], using a XtaLAB Synergy, Dualflex, HyPix four-circle diffractometer, a micro-focus sealed X-ray tube and a HyPix detector. The data were corrected using SCALE3 ABSPACK and the structure were solved using SHELXT

Asymmetric organocatalytic synthesis of chiral homoallylic amines

• Nikolay S. Kondratyev and
• Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

• ’-dibromo-BINOL [25]. aAbsolute configuration was confirmed by a single crystal XRD of the corresponding hydrochloride salt. (R)-3,3’-Di(3,5-di(trifluoromethyl)phenyl-BINOL-catalysed asymmetric geranylation and prenylation of dihydroisoquinolines [25]. aAbsolute configuration was established by single

• crystal XRD of the corresponding hydrochloride salt. Microwave-induced one-pot asymmetric allylation of in situ-formed arylimines, catalysed by (R)-3,3’-diphenyl-BINOL. Aldehyde and amine scope [26]. aThe reaction was conventionally heated at 50 °C for 24 hours instead of microwave irradiation. b1.0 equiv

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• . Isolated yield of 17:18 with ratios determined from the 1H NMR spectra. Supporting Information Supporting Information File 42: Experimental procedures and characterisation data, additional cyclisation studies, XRD data and NMR spectra of compounds. Acknowledgements The authors gratefully acknowledge

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• were isolated preparatively and fully characterized by IR, 1H, and 13C NMR spectroscopy as well as HRMS and XRD methods. The reverse thermal reaction was catalyzed by protonic acids. N-Acylated compounds exclusively with Fe2+ formed nonfluorescent complexes with a contrast naked-eye effect: a color

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• 5. As the XRD study of the crystals showed (Figure 3), the molecular and crystal structure of the isolated compound is strongly dominated, on the one hand, by intra- and intermolecular hydrogen bonds with the participation of N, Cl, and O heteroatoms (forming an endless slightly corrugated ribbon

• compounds 5·HBF4 and 8·HBF4 were recrystallized from acetonitrile and subjected to XRD analysis under the same conditions. Selected data obtained are shown in Table 1. As can be seen, in both protonated quinoquinoline systems, an intramolecular hydrogen bond is realized (strongly asymmetric in crystals, but

• between (Supporting Information File 1, Figure S22). Flat dipyridoacenaphthylene cations 8H+ give a denser packing, which, with an interplanar distance of only 3.328 Å, is the closest among all the studied compounds. Conclusion Using single crystal XRD technique, dipyridoacenaphthene tetrafluoroborate

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• . Crystallography Crystals of CAAC·CS2 zwitterions 4a and 4c suitable for X-ray diffraction (XRD) analysis were grown by slow diffusion of cyclohexane in a THF solution at 6 °C. Their molecular structures are depicted in Figure 3. The orange-red needles of compound 4a belonged to the trigonal space group, while

• layered with petroleum ether or n-hexane and kept at −18 °C for a few weeks. This procedure successfully afforded single crystals of products 6b and 6e suitable for XRD analysis (Figure 4). Orange prisms of zwitterion 6b belonged to the monoclinic P21/n space group, while the dark red-brown blocks of

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• @C2v-C82(CHClC6H3Cl2) [19] and La@C2v-C82(CBr(CO2Et)2) [23], by single-crystal X-ray diffraction (SC-XRD) analysis. Based on the similarity in the absorption spectra of La@C2v-C82(CHClC6H3Cl2), the addition site of 3a–c was expected to be at the C10 (for the numbering of carbon atoms in La@C2v-C82; see

• 3a was confirmed by the SC-XRD analysis, which showed that the addition site of addendum was indeed at the C10 position of La@C2v-C82 (Figure 5). The La@C2v-C82 anion can act as an electron donor and a nucleophile. To confirm the reaction mechanism, charge density and the p-orbital axis vector (POAV

• , assuming that La@C2v-C82 and the monoadducts have the same absorption coefficients. X-ray crystallography Black crystalline rods of 3a were obtained using the liquid–liquid bilayer diffusion method with 3a in a CS2 solution and an n-hexane solution in a glass tube (⌀ = 7 mm) at room temperature. The SC-XRD

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• 1758 cm−1 (C=O). X-ray diffraction (XRD) measurements of 1 and 2 are shown in Figure 2. The Miller indices indicate the Colhex and Colrect character of the mesophases [31]. Despite crystallization of 2, the Colrect order is partially preserved at room temperature. The Colhex lattice parameter (a

• square roughness (Rrms) of 1.7 nm and 2.8 nm for 1 (Figure 5a) and 2 (Figure 5b), respectively. The Rrms of the films deposited on Al for the electron-only devices are 1.1 nm for 1 (Figure 5c) and 16.0 nm for 2 (Figure 5d). XRD measurements of as-casted spin-coated films of 1 and 2 confirm their columnar

• the autofocus. XRD measurements were performed with an X’Pert PRO (PANalytical) diffractometer using Cu Kα radiation (λ = 1.5418 Å) equipped with an X’Celerator detector. A small amount of 1 or 2 was deposited onto a glass substrate and heated to the isotropic liquid phase. The diffracted radiation

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

• liquors and, in both cases, XRD confirmed the obtention of the (E)-isomer, in an anti-conformation. Computational calculations (gas and water phases) were performed in order to confirm some of the structural and vibrational aspects of the compounds. An important intramolecular H bond involving the

• ; phenol acidity; ring substituents; XRD; Introduction N-Acylhydrazones are a class of compounds that contain the hydrazonic functional group (–NH–N=C–) attached to an acyl group, which can be modified to generate a range of different structures with varying properties [1]. The versatility of this class

• vibrational aspects of the compounds. The optimized structures obtained with B3LYP/6-311G(d,p) (both in gas and water phases) were compared to the respective experimental XRD structures (Figure 3). The RMSD values for hdz-NO2 in gas (0.431 Å) and water (0.405 Å) phases were lower than the respective values

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• anion. The formed receptor: ion-pair 1:1 complex 4-CsF was stable in solution, as evidenced by 1H NMR spectroscopy. The binding constant Ka = 3.8·105 M−1 in CHCl3/MeOH 9:1 was reported. The XRD analysis in the solid state provided further proof of the binding mode, demonstrating the significant

• , accommodating the axially-positioned water molecule on the cobalt(III) centre. The latter assembled into a remarkable hexagonal wheel architecture when exposed to air in THF, as evidenced by XRD (Figure 12). The hexagonal wheel [16-Co(III)]6 was stabilised by intramolecular hydrogen bonding between the water

• nitrogen in the middle of the ether chain of 19-Cr. The reaction between in situ generated 17-K2 or 19-K2 and CoCl2 produced paramagnetic cobalt(II) complexes 17-Co or 19-Co [67]. The XRD analysis of 17-Co revealed a molecular structure with distorted octahedral Co(II) coordinating water and hydroxide

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

• Grédy Kiala Kinkutu,
• Catherine Louis,
• Myriam Roy,
• Juliette Blanchard and
• Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

• Supporting Information File 20: Experimental and copies of spectra. Acknowledgements The authors acknowledge MS3U of Sorbonne Université for HRMS analysis and CNRS. We also thank J. Forté for the XRD analyses (IPCM) and A. Miche for the XPS analyses (LRS). Funding The authors acknowledge H2020-WIDESPREAD-05

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• [7]. It is important to know the conformational capabilities of such ligands for construction of such complexes [8][9][10][11]. However, to date, XRD data on phosphorus derivatives containing a ferrocenyl substituent at the sulfur atom are presented only in oxidized and sulfurized forms

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• phenylacetylene in the presence of a series of PdCo bimetallic nanoparticles with different compositions on graphite sheets as highly active catalysts (Scheme 27) [40]. The catalyst was prepared by a chemical reduction method and characterized by various techniques like Raman, XRD, TEM, and XPS. The Pd/Co(1:1)NPs

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• XRD data (Figure 1). In order to select optimal conditions for the synthesis of compounds 3, the oxidative systems have been varied for the reactions of tetrazines 2a,b,g bearing methyl, phenyl, and pyrazolyl substituents. Attempts to use Pb(OAc)4 as an oxidizing agent in CHCl3 resulted in the

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• interchanged. However, to our delight only the formation of the desired species 1a occurred, as evidenced by two-dimensional NMR measurements (for atom labeling scheme used for assignment of resonances see Figure S1 in Supporting Information File 1) and confirmed by SC-XRD (Figure 2), being in agreement with

• [2,3-d][1]benzazepin-6(5H)-one (3a). This procedure delivered analytically pure 3a in 80% yield as also confirmed by SC-XRD (Figure 3). The final step to structure C required removal of the benzyl group. Debenzylation of amines is commonly performed by palladium-catalyzed hydrogenation [40]. However

• glacial acetic acid at 100 °C gave 1c in 53% yield. Compound 2c was obtained by palladium-catalyzed reduction of 1c with hydrogen in an excellent yield and its structure was confirmed by SC-XRD (Figure S4 in Supporting Information File 1). The following ring-closure reaction of 2c with trimethylaluminum