Synthesis of new tetra- and pentacyclic, methylenedioxy- and ethylenedioxy-substituted derivatives of the dibenzo[c,f][1,2]thiazepine ring system

• Gábor Berecz,
• András Dancsó,
• Mária Tóthné Lauritz,
• Loránd Kiss,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2645–2656, doi:10.3762/bjoc.21.205

• -crystal X-ray diffraction (SC-XRD) measurements were carried out on a Rigaku R-Axis Spider diffractometer with an imaging plate area detector using graphite monochromatic Cu Kα radiation. Single crystal X-ray structures were deposited at the Cambridge Crystallographic Data Centre under the following

• the dibenzo[c,f][1,2]thiazepine (1) skeleton. Drugs exhibiting a 1,3-benzodioxole or 1,4-benzodioxane structural unit marketed or in development. X-ray structures of compounds 20e and 21g. X-ray structure of compound 23a. X-ray structures of compounds 25, 26, and 27. Synthesis of tetracyclic key

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

• diffractometer with an imaging plate area detector using graphite monochromatic Cu Kα radiation. Single crystal X-ray structures were deposited at the Cambridge Crystallographic Data Centre under the following numbers: CCDC 2447633 (3b), CCDC 2447638 (3d), CCDC 2447632 (3e), CCDC 2447636 (3g), CCDC 2447639 (3h

• the excitation of NH) spectra of (E)-7h. 1H NMR and selective 1D NOESY (with the excitation of NH) spectra of (Z)-7h. X-ray structures of compounds 3d (A), 7d (B), (Z)-7h (C), and (E)-9a (D). The capacity factor (logk) vs calculated partition coefficients (clogP) by ACD Labs/Percepta [36]); the

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• -substituted diazocines were prepared via Stille, Suzuki, and Buchwald–Hartwig reactions. X-ray structures are presented for derivatives 1, 2 and 7. Keywords: cross-coupling; diazocine; N-acetyl diazocine; photoisomerization; photoswitch; thermal relaxation; Introduction Diazocines are frequently used

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• '-hexafluoro-6,6',7,7',10,10',11,11'-octakisalkoxy-2,2'-bitriphenylene dimers (G55, G66 and G48). Mesophases’ parameters. Supporting Information Synthesis (Schemes S1–S3) and characterization, 1H, 13C, and 19F NMR (Figures S1–S21), HRMS (Figures S22–S32), EA, single crystal X-ray structures (Figures S33, S34

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• were carried out by using the Gaussian 16 program [31]. Triazatriangulenium cations 1a+ and 1b+. Synthesis of triazatriangulenium ion pairs 2+-X− (X− = BF4−, PF6−, B(C6F5)4−, and PCCp−). Single-crystal X-ray structures of (a) 2+-Cl−, (b) 2+-BF4−, (c) 2+-PF6−, (d) 2+-B(C6F5)4−, and (e) 2+-PCCp− as (i

• +-Cl−, (b) 2+-BF4−, and (c) 2+-PF6−. Atom color code: yellow, green, orange, and green (spherical) refer to boron, fluorine, phosphorus, and chlorine, respectively. (i) Single-crystal X-ray structures and (ii) interaction energies for the pairs (a) 2+-Cl−, (b) 2+-BF4−, and (c) 2+-PF6−. In (i), the

• ) Single-crystal X-ray structures and (ii) interaction energies for the pairs for (a) 2+-B(C6F5)4− and (b) 2+-PCCp−. In (i), the cation and the anion are represented in cyan and magenta colors, respectively. Crystallographic details. Supporting Information Supporting Information File 136: 1H, 13C, and 19F

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• the X-ray structures of catechols 6, and 8 are shown in Figure 2. The geometrical characteristics of catechol moieties of these compounds, in general, have the standard parameters: the bonds C1–O1, C2–O2 are 1.369(11) and 1.377(9) Å in 5, 1.371(2) and 1.387(2) Å in 6, 1.389(3) and 1.377(3) Å in 8; the

• ellipsoids of 50% probability). The hydrogen atoms except those of hydroxy groups are omitted. The X-ray structures of catechols 6 (a) and 8 (b) (the thermal ellipsoids of 50% probability). The hydrogen atoms except those of hydroxy groups are omitted. Fragment of the pack of catechol 5 in crystal (the H

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• governed the regioselectivity. Reactivities of norcorroles with various reagents. Top and side views of the X-ray structures of a) 2a and b) 1 [2]. Mesityl groups and hydrogen atoms were omitted for clarity. Thermal ellipsoids are drawn at 50% probability. UV–vis–NIR absorption spectra of 1 and 2a in

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• Supporting Information File 1). DFT calculations were carried out to gain further insight into the structures of iodine(V) fluorides 21 and 22 whose X-ray structures could not be obtained, and hypothetical iodine(V) amides 7a and 7b which could not be made. Comparisons were made with iodine(V) compounds 6

(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

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

• concentrations of 1a. Photocatalytic CO2 reduction tests with different concentrations of HFIP.a Supporting Information Additional information regarding the instrumentation, structural analyses, and X-ray structures is provided. Crystal structures were deposited in the Cambridge Crystallographic Data Centre

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• : (i) FAIR open data from X-ray structures and Mercury® 2020.1 Software (Cambridge Crystallographic Data Center) to create Figures 1b (CCDC number 1943103), 3b (CCDC number 2018646) and 4 (CCDC numbers 2090727 and 2090729); (ii) chemical structures employing ChemBioDraw® Ultra 12.0 (CambridgeSoft

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• the extent of π-conjugation and the efficiency of particular donor–acceptor conjugation path in these new compounds. X-ray structures and absorption spectra of doubly protonated tetrafluoroborate salts of the oligomers are also discussed. Keywords: 1,8-bis(dimethylamino)naphthalene; cross-conjugated

• were obtained in good yields regardless of the substituent R in the benzene ring. Treatment of the latter with fluoroboric acid in dichloromethane gave double salts 11a–e. X-ray structures Slow evaporation of solutions of butadiynes 5 in the CHCl3/EtOAc system made it possible to grow single crystals

Synthesis, α-mannosidase inhibition studies and molecular modeling of 1,4-imino-ᴅ-lyxitols and their C-5-altered N-arylalkyl derivatives

• Martin Kalník,
• Sergej Šesták,
• Juraj Kóňa,
• Maroš Bella and
• Monika Poláková

Beilstein J. Org. Chem. 2023, 19, 282–293, doi:10.3762/bjoc.19.24

• active site almost identical to those of human GMII [22]. In addition, analysis of the available X-ray structures of GH38 enzymes such as dGMII [23], bovine lysosomal α-mannosidase II (bLMan) [17] and JBMan [24] showed that the active sites of Golgi and acidic α-mannosidases are structurally very similar

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• estimates obtained consequently correlated with the results from the 1H NMR analyses to varying degrees from very good to fair. PXRD patterns generated from the final single crystal X-ray structures were in good agreement with the respective PXRD patterns of the CD complexes formed via co-precipitation

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• /methanol, this H-bond is broken and two new H-bonds are formed resulting in a less strained structure with a normal pyramidal geometry of the N-4 nitrogen atom. The calculated structural metrics of complexes modeled by DFT are close to those observed in the X-ray structures. The formation of inclusion

• -tetraazaadamantane motif in X-ray structures of the obtained N-TAAD derivatives (representation of non-hydrogen atoms as thermal ellipsoids at 50% probability level). Anions and crystal-solvate molecules are omitted for clarity. (a) 4a·HCl·H2O·MeOH. (b) 4c·HCl·3.5MeOH. (c) Bn-4c·3CD3OD (bromide salt). (d) 8a. (e

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

• Dajana Barišić,
• Mario Pajić,
• Ivan Halasz,
• Darko Babić and
• Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

• Information Supporting Information File 167: Detailed experimental procedures, complete characterization data for new compounds, X-ray structures of compounds, and the results of in situ Raman monitoring. Supporting Information File 168: X-ray crystallographic data. Funding Financial support was provided by

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

• Kian Donnelly and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

• solving all X-ray structures reported in this article. Funding M.B. thanks the Royal Society of Chemistry for a Research Enablement Grant (E20-2998) as well as Science Foundation Ireland for generous support of our research program through grants 19/IFA/7420, 18/RI/5702 and 12/RC2275_P2. Support from the

Structural effects of meso-halogenation on porphyrins

• Keith J. Flanagan,
• Maximilian Paradiz Dominguez,
• Zoi Melissari,
• Hans-Georg Eckhardt,
• René M. Williams,
• Dáire Gibbons,
• Caroline Prior,
• Gemma M. Locke,
• Alina Meindl,
• Aoife A. Ryan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

• . Additionally, we have used density functional theory calculations to determine the structure of several halogenated porphyrins. This contrasts conformational analysis with existing X-ray structures and gives a method to characterize samples that are difficult to crystallize. By using the methods outlined above

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

• Vladimir Kubyshkin,
• Rebecca Davis and
• Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

• Vladislav A. Budevich,
• Sergei V. Voitekhovich,
• Alexander V. Zuraev,
• Vadim E. Matulis,
• Vitaly E. Matulis,
• Alexander S. Lyakhov,
• Ludmila S. Ivashkevich and
• Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

• -containing alkylation reagents [27]. Very recently, this aminide was found to be a suitable ligand for manganese complexes [28] and used as the agent for the preparation of salts with high energy density [29]. Also, it is worth noting that today only a few examples of mesoionic tetrazole aminide X-ray

• structures are known [17][28]. Thus, the information on tetrazole-5-aminides is very limited and fragmentary. In the present work, we try to fill this gap by carrying out experimental (synthesis, X-ray, UV–vis) and theoretical density functional theory (DFT) studies of some selected 1,3-dialkyltetrazolium-5

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

• Daria I. Tonkoglazova,
• Anna V. Gulevskaya,
• Konstantin A. Chistyakov and
• Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

• were used as starting materials. To discern the effect of merging an azine moiety within a helical skeleton, the X-ray structures, UV–vis absorption and fluorescence spectra of the helicenes were investigated and compared to that of the parent carbazole-based [6]helicene (7H-phenanthro[3,4-c]carbazole

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

• Csilla Hargitai,
• Györgyi Koványi-Lax,
• Tamás Nagy,
• Péter Ábrányi-Balogh,
• András Dancsó,
• Gábor Tóth,
• Judit Halász,
• Angéla Pandur,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

• shown by the X-ray structures of these compounds (Figure 1 and Figure 3), and also reflected by their low 3J(H,H) coupling constants (ca. 1 Hz) detected in CDCl3 solution. In the 1H NMR spectra of compounds 3b, 8a,b, and 23a, the δΝΗ chemical shifts appeared in a narrow range between 9.39–9.06 ppm

• (182 mg, 18%) was isolated as white solid. Analytical data are identical with those described in Method A. X-ray structures of compounds 3b (left) and 8b (right). Gibbs free energy diagram for the 1→2 rearrangement. X-ray structures of compounds 23a (left) and 23b (right). Structures of the minimal

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• rotaxane 1a (top) and thread 4a (bottom) in CDCl3 (a designation of the signals is described in Figure 2). 1H,1H-ROESY NMR spectrum (600 MHz) of the rotaxane 1a in CDCl3. Cyclic voltammogram of ferrocene rotaxane 1a (0.67 mM) in CH2Cl2/CH3CN 1:5 (TBAPF6 0.10 M, scan rate = 10 mV/s). Single crystal X-ray

• structures of (a) rotaxane 1a and (b) Leigh’s rotaxane I [4]. Selected H···O distances from the solid-state structures. Supporting Information Supporting Information File 71: Further experimental details and NMR spectra of new compounds. Supporting Information File 72: X-ray data of rotaxane 1a

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

• Carlos H. Escalante,
• Eder I. Martínez-Mora,
• Carlos Espinoza-Hicks,
• Alejandro A. Camacho-Dávila,
• Fernando R. Ramos-Morales,
• Francisco Delgado and
• Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

• 8b/7c and 8c/7c (Figure 4a,b and Supporting Information File 1, Appendix 6). All the observable π···π interactions were parallel-displaced (offset) π-stacking, and the distance values were within the range of the known values, whether determined from X-ray structures or calculated values (3.2–4.0 Å

A combinatorial approach to improving the performance of azoarene photoswitches

• Joaquin Calbo,
• Aditya R. Thawani,
• Rosina S. L. Gibson,
• Andrew J. P. White and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

• geometry of ortho-halogenated Z-arylazopyrazoles. Description of the lowest-lying n–π* excitation for the Z-isomers of halogenated 4pzH-F2 and 4pzH-Cl2 photoswitches. Description of the lowest-lying n–π* excitation for the E-isomers of halogenated 4pzH-F2 and 4pzH-Cl2 photoswitches. X-ray structures of