Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands

• Jennifer Klose,
• Tobias Severin,
• Peter Hahn,
• Alexander Jeremies,
• Jens Bergmann,
• Daniel Fuhrmann,
• Jan Griebel,
• Bernd Abel and
• Berthold Kersting

Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81

• Table S4 in Supporting Information File 1. Structure of the [Zn2L(μ-azo-OH)]+ cation in crystals of [Zn2L(μ-azo-OH)][Zn2L(μ-azo-O)]·4MeCN·3H2O (3'·4MeCN·3H2O). Hydrogen atoms omitted for clarity. Thermal ellipsoids are drawn at the 50% probability level (color codes: C dark grey, H pale gray, N green/or

• of [Cd2L(μ-azo-NMe2)]ClO4·0.5MeOH (6·0.5MeOH). Only one orientation of the disordered azobenzene carboxylato co-ligand is displayed. Hydrogen atoms omitted for clarity. Thermal ellipsoids are drawn at the 50% probability level. Space filling representation of the packing of four [Cd2L(μ-azo-NMe2

• ·8EtOH (7·8EtOH). Only one orientation of the disordered azo-carboxylato co-ligand is displayed. Hydrogen atoms omitted for clarity. Thermal ellipsoids are drawn at the 50% probability level. Left: ORTEP representation of the molecular structure of the [Cd2L(μ-azo-CO2Me)]+ cation in crystals of 8·MeCN

Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry

• Gábor Benkovics,
• Mihály Bálint,
• Éva Fenyvesi,
• Erzsébet Varga,
• Szabolcs Béni,
• Konstantina Yannakopoulou and
• Milo Malanga

Beilstein J. Org. Chem. 2019, 15, 710–720, doi:10.3762/bjoc.15.66

• the tosylation of 6-monoazido-β-CD in pyridine is selective for the primary rim and gives the three regioisomers with equal probability. Reaction 10 also gave only three components in 37:32:31 area ratio (reaction 10, Figure 6), identified as 6A,6D-, 6A,6C- and 6A,6B-diazido-β-CD, which definitely

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

• Rodrigo Abonia,
• Luisa F. Gutiérrez,
• Braulio Insuasty,
• Jairo Quiroga,
• Kenneth K. Laali,
• Chunqing Zhao,
• Gabriela L. Borosky,
• Samantha M. Horwitz and
• Scott D. Bunge

Beilstein J. Org. Chem. 2019, 15, 642–654, doi:10.3762/bjoc.15.60

• 9. aThis product was obtained as an inseparable mixture along compound 8{9,9,6} (see Supporting Information File 1). Thermal ellipsoid plot (40% probability level) of the tris(heteroaryl)methane triad 9{4,7,1}. DFT-optimized structure of 9{4,7,1} triad. 1D- and 2D-based NMR assignments for methylium

Silanediol versus chlorosilanol: hydrolyses and hydrogen-bonding catalyses with fenchole-based silanes

• Falco Fox,
• Jörg M. Neudörfl and
• Bernd Goldfuss

Beilstein J. Org. Chem. 2019, 15, 167–186, doi:10.3762/bjoc.15.17

• -interactions with dotted lines (M06-2X-D3/6-311++G(d,p)(PCM=THF)//B3LYP-D3BJ/6-31G(d) at 298 K). X-ray crystal structure of BIFOXSiCl2 (7). H atoms on the chiral backbone are omitted for clarity issues and the ellipsoids are shown with 65% probability. X-ray crystal structure of BIFOXSiCl(OH) (8). H atoms on

• the chiral backbone are omitted for clarity issues and the ellipsoids are shown with 65% probability. X-ray crystal structure ofrac-BIFOXSi(OH)2 (9) forming dimers. H atoms on the chiral backbone are omitted for clarity issues and the ellipsoids are shown with 65% probability. For bond lengths and

• angles see Table 5. X-ray crystal structure of BIFOXSi(OH)2 (9) forming a tetramer. H atoms on the chiral backbone are omitted for clarity issues and the ellipsoids are shown with 65% probability. For bond lengths and angles see Table 5. X-ray crystal structure of BIFOXSi(OH)2 (9) forming a dimeric

New standards for collecting and fitting steady state kinetic data

• Kenneth A. Johnson

Beilstein J. Org. Chem. 2019, 15, 16–29, doi:10.3762/bjoc.15.2

• . More precisely, kcat/Km is equal to the true second order rate constant for substrate binding to the enzyme multiplied by the probability that the bound substrate will be converted to product and released into solution. This principle can be illustrated using the simplest model: The term, k2/(k−1 + k2

• ), gives the probability that the substrate reacts rather than dissociating. With more realistic models, the more complex equations for kcat/Km can still be understood as the product of the rate constant for substrate binding times the probability of forward reaction. Interpretation of steady state kinetic

Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines

• Olga A. Storozhenko,
• Alexey A. Festa,
• Delphine R. Bella Ndoutoume,
• Alexander V. Aksenov,
• Alexey V. Varlamov and
• Leonid G. Voskressensky

Beilstein J. Org. Chem. 2018, 14, 3078–3087, doi:10.3762/bjoc.14.287

• annulation patterns. Biologically relevant imidazo[1,2-a]pyridines and chromenes. General view of the molecule 7b in the crystal state (CCDC 1849215). Anisotropic displacement parameters are drawn at 50% probability. Domino formation of imidazopyridines and current work. Scope of the reaction between N

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• . A probability value of p ≤ 0.05 was considered statistically significant. Murine model for corneal infection The corneas of the C57BL/6 mice were scratched with a scraper to create wounds. 10 µL of PAO1 planktonic cells (≈1 × 106 cells) were dripped onto each cornea and incubated for 24 h on the

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• observed with a total trans-diastereoselectivity controlled by intramolecular hydrogen bonds. Chemical structures of analogues. NOEs correlation showing the stereochemistry of the compound 5a. X-ray crystal structure of 5f shown at the 30% probability level. Strategy for the formation of 1-(arylamino)-1H

Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Brønsted acids. NMR and DFT study of these cations and their reactions

• Stanislav V. Lozovskiy,
• Alexander Yu. Ivanov,
• Olesya V. Khoroshilova and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2018, 14, 2897–2906, doi:10.3762/bjoc.14.268

• (CCDC 1843239); ellipsoid contours of probability levels are 50%. (Arylsulfinyl)allenes 1 and (arylsulfonyl)allenes 2 used in this study. Plausible reaction mechanisms of transformations of allene 2a in Brønsted acids. Selective formation of butadienes 3a–h from allenes 2a–h. Reactions of allenes 2 in

The influence of the cationic carbenes on the initiation kinetics of ruthenium-based metathesis catalysts; a DFT study

• Magdalena Jawiczuk,
• Angelika Janaszkiewicz and
• Bartosz Trzaskowski

Beilstein J. Org. Chem. 2018, 14, 2872–2880, doi:10.3762/bjoc.14.266

• catalysts the ammonium tag is relatively far from the carbene carbon atom chelating the ruthenium core. The reason behind such design was likely the low probability of the ammonium tag influencing the ruthenium core and therefore, having a potential negative effect on the efficiency and reaction rate of the

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus

• Jakob Bouton,
• Kristof Van Hecke,
• Reuven Rasooly and
• Serge Van Calenbergh

Beilstein J. Org. Chem. 2018, 14, 2822–2828, doi:10.3762/bjoc.14.260

• . Structures of hamamelitannin (1), lead compound 2 and target compounds 3. Molecular X-ray structure of 3a, showing thermal displacement ellipsoids at the 50% probability level. Positional disorder of the chlorophenyl ring and the water solvent molecule are not shown. Proposed strategy for the synthesis of

Domino ring-opening–ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles

• Ritabrata Datta and
• Subrata Ghosh

Beilstein J. Org. Chem. 2018, 14, 2708–2714, doi:10.3762/bjoc.14.248

• –ESI m/z: [M + Na]+ calcd for C30H44O7SiNa 567.2754; found, 567.2756. Structures of retigeranic acids A (1a) and B (1b). ORTEP of compound 13 (ellipsoids at 30% probability). Probable metathesis intermediates. Metathesis of norbornene derivatives. Synthesis plan. Metathesis of norbornene derivatives 7a

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

• Henrike Ehrhorn,
• Janin Schlösser,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

• applications of alkyne metathesis since this protocol represents a convenient approach to alkyne metathesis catalysts in two steps starting from WCl4. Selected homogeneous catalysts for alkyne metathesis. Molecular structure of W2F3·NHMe2 with thermal displacement parameters drawn at 50% probability. Hydrogen

• atoms are omitted for clarity. Molecular structure of WPhF3 with thermal displacement parameters drawn at 50% probability. Hydrogen atoms and minor components of the disordered OC(CF3)Me2 groups are omitted for clarity. Conversion versus time diagram for the self-metathesis of 1-phenyl-1-propyne

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

• Jiang Liu,
• Peter Leonard,
• Sebastian L. Müller,
• Constantin Daniliuc and
• Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

• ellipsoids are drawn at the 50% probability level and H-atoms are shown as small spheres of arbitrary size. Hydrogen bonds are shown as dashed lines. The crystal packing of 8 shows the intramolecular hydrogen-bonding network (projection parallel to the x-axis). N- and S-conformation for cyclonucleoside 8. B

Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds

• Liudmila L. Rodina,
• Xenia V. Azarova,
• Jury J. Medvedev,
• Dmitrij V. Semenok and
• Valerij A. Nikolaev

Beilstein J. Org. Chem. 2018, 14, 2250–2258, doi:10.3762/bjoc.14.200

• tetrahydrofuran used in the project. Molecular structure of hydrazone 2b as determined by X-ray analysis data (Olex2 plot with 50% probability level of ellipsoids). Photochemical cycloelimination of furans from hydrazones 2d,e. Different pathways of diazodiketones 1 light-induced reactions in the singlet

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

• Maroš Bella,
• Sergej Šesták,
• Ján Moncoľ,
• Miroslav Koóš and
• Monika Poláková

Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

• adjacent ChemDraw image) of compound 20. Atomic displacement ellipsoids are drawn at 50% probability level. Synthesis of pyrrolidines 2a and 3a. Synthesis of pyrrolidines 2b,c and 3b,c. Synthesis of pyrrolidines 4. Synthesis of pyrrolidines 5. Inhibitory activity of pyrrolidines 2–5 against the class II α

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Mikhail A. Syroeshkin,
• Alexander A. Korlyukov,
• Pavel V. Dorovatovskii,
• Yan V. Zubavichus,
• Gennady I. Nikishin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

• . bDMP (0.15 mmol) was used instead of PhI(OAc)2, reaction time 30 min. Molecular structure of 3ca. Atoms are presented as anisotropic displacement parameters (ADP) ellipsoids (50% probability). For clarity, only one set of positions of the disordered ethylene bridge and Ph groups is shown. CV curves of

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

• James T. Fletcher,
• Matthew D. Hanson,
• Joseph A. Christensen and
• Eric M. Villa

Beilstein J. Org. Chem. 2018, 14, 2098–2105, doi:10.3762/bjoc.14.184

• -formyltriazole analogs via ring-degenerate rearrangement of 1-substituted-4-imino-1,2,3-triazoles as first described by L’abbé [42]. ORTEP structure of 2cc’. Thermal ellipsoids shown at 25% probability. 1H NMR aromatic region of a product mixture compared with reference imine analogs. Singlets appearing from 8.5

D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation

• Michael R. Imrich,
• Jochen Kraft,
• Cäcilia Maichle-Mössmer and
• Thomas Ziegler

Beilstein J. Org. Chem. 2018, 14, 2082–2089, doi:10.3762/bjoc.14.182

• ligands 2 and 3 and spiro-fused PyOx and PHOX ligands 4 and 5. Molecular structure of 10j. Ellipsoids are given at the 50% probability level. Grey = carbon, red = oxygen, white = hydrogen, purple = nitrogen, orange = bromine. Preparation of 1,2-isopropylidene-protected D-fructose derivatives with

Chiral bisoxazoline ligands designed to stabilize bimetallic complexes

• Deepankar Das,
• Rudrajit Mal,
• Nisha Mittal,
• Zhengbo Zhu,
• Thomas J. Emge and
• Daniel Seidel

Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175

• the development of new catalytic enantioselective transformations. Examples of chiral bimetallic complexes utilized in asymmetric catalysis. Previously reported bisoxazoline ligands capable of stabilizing bimetallic complexes. Thermal ellipsoid plot (50% probability) of the molecular structure of 16

• with a = 14.1829(5) Å, b = 14.8645(6) Å, c = 25.2342(10) Å, α = 90°, β = 90°, γ = 90°, V = 5319.9(4) Å3, Z = 4, Dc = 1.450 mg m−3 and μ(Mo Kα) = 1.017 mm−1. Thermal ellipsoid plot (50% probability) of the molecular structure of 25·Ni2(OAc). Hydrogen and solvate atoms have been omitted for clarity: (A

• (2)°, γ = 90°, V = 1759.0(3) Å3, Z = 2, Dc = 1.614 mg m−3 and μ(Mo Kα) = 1.281 mm−1. Thermal ellipsoid plot (50% probability) of the molecular structure of 30·Pd2Br. Hydrogen and solvate atoms have been omitted for clarity: (A) view normal to the mean molecular plane; (B) side view nearly

Synthesis and characterization of π–extended “earring” subporphyrins

• Haiyan Guan,
• Mingbo Zhou,
• Bangshao Yin,
• Ling Xu and
• Jianxin Song

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

• . Thermal ellipsoids are drawn at the 50% probability level. All hydrogens on tolyl groups are omitted for clarity. Partial 1H NMR spectrum of 3Pd. X-ray crystal structures of 3Pd: a) top view; b) side view. Thermal ellipsoids are at the 30% probability level. All hydrogens on tolyl are omitted for clarity

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• of the mannoside are varied. In 5 a bis-diazirine functionalization is suggested to increase labeling probability. Connolly representation of photolabile α-D-mannoside 3 in the closed gate (A, PDB code 1UWF) and open gate crystal structure of FimH (B, PDB code 1KLF) [24]. The surface is colored

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

• Siva Sankar Murthy Bandaru,
• Darinka Dzubiel,
• Heiko Ihmels,
• Mohebodin Karbasiyoun,
• Mohamed M. A. Mahmoud and
• Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

• tuning of the stereoelectronic or steric properties of substituents. Structures of 9-substituted benzo[b]quinolizinium derivatives 1 and 2. Molecular structures of derivatives 2a (top) and 2b (bottom) in the solid state. Ellipsoids are shown at the 50% probability level. The counter anions and solvent

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

• Alphonse Fiebor,
• Richard Tia,
• Banothile C. E. Makhubela and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

• in literature [40]. The crystal structure of 17d also shows a static disorder of a CH2 carbon of one of the sec-butyl groups (C14). The atom site occupancy factors of the two positions of the CH2 carbon atom was refined to 0.571(11) and 0.429(11). This shows that the carbon atom has equal probability