Insertion of [1.1.1]propellane into aromatic disulfides

• Robin M. Bär,
• Gregor Heinrich,
• Martin Nieger,
• Olaf Fuhr and
• Stefan Bräse

Beilstein J. Org. Chem. 2019, 15, 1172–1180, doi:10.3762/bjoc.15.114

• peroxide, DTBP) led to increased amounts of insoluble polymer. Molecular structure of 6a (displacement parameters are drawn at 50% probability level), distance C1–C3 1.844(3) Å. NMR spectra of pure 6a (green) and 6d (red) and the obtained mixture with the new compound 15 (blue). Summary of the most recent

• structure of 14 could be proven by single-crystal X-ray diffraction (displacement parameters are drawn at 50% probability level). Reaction of propellane (1) with the two disulfides 10a and 10d. When two different disulfides were used, all three possible products were obtained. The yields were determined by

• by single-crystal X-ray diffraction (displacement parameters are drawn at 50% probability level). Results of the insertion of 1 into aromatic disulfide bonds. The ratio of 1:10 determines the amount of [2]staffane formed. Supporting Information Full experimental details and analytical data (1H NMR

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• Heck cyclization reaction between the substituted alkyne and aryl bromide in 133 takes place to form a cyclic palladium intermediate 134 with E-configuration, resulting from a syn-addition mechanism of this step. The addition of a silver salt reduces the probability of isomerization of the double bond

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• structure of 1-([1,1'-biphenyl]-4-yl)-5-oxo-7-phenyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-3-aminium 2,2,2-trifluoroacetate 9i according to X-ray diffraction data. Thermal ellipsoids of atoms are shown at 50% probability level. Molecular structure of 3-(2-amino-4-phenyl-1H-imidazol-5-yl)-3-(p-tolyl

• )propanoic acid 11b according to X-ray diffraction data. Thermal ellipsoids of atoms are shown at 50% probability level. Molecular structure of aminoimidazo[1,2-c]pyrrole 16a according to X-ray diffraction data. Thermal ellipsoids of atoms are shown at 50% probability level. 3,3’-Spirooxindole alkaloids

• . Molecular structure of aminoimidazo[1,2-c]pyrrole 19a according to X-ray diffraction data. Thermal ellipsoids of atoms are shown at 50% probability level. The three component condensation of imidazo[1,2-a]pyridine, aldehydes and Meldrum’s acid described by Gerencsér at al. [31]. Two forms of cation 9i

An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride

• Aytekin Köse,
• Aslı Ünal,
• Ertan Şahin,
• Uğur Bozkaya and
• Yunus Kara

Beilstein J. Org. Chem. 2019, 15, 931–936, doi:10.3762/bjoc.15.89

• for C10H13ClN2O3S, 276.7350; found, 277.0434. The dipolar intermediate formed in the reaction of CSI with olefins. (a) Molecular structure of racemic molecule 10 (asymmetric unit). Thermal ellipsoids are drawn at the 30% probability level. (b) Geometric parameter with H-bonded geometry. Hydrogen bonds

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

• Razieh Navari,
• Saeed Balalaie,
• Saber Mehrparvar,
• Fatemeh Darvish,
• Frank Rominger,
• Fatima Hamdan and
• Sattar Mirzaie

Beilstein J. Org. Chem. 2019, 15, 874–880, doi:10.3762/bjoc.15.85

• molecules based on the pyrazolopyridine framework. ORTEP Structure of compound 4a and intermolecular hydrogen bonding; the ellipsoid probability level of each ORTEP diagram is 50%. Structures of synthesized pyrazolopyridines 4a–m. Reaction conditions: 3-formylchromone derivatives (1 mmol), primary amine

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• excitation is possible because the probability of TP excitation is proportional to the square of the light intensity [46]. The light-induced generation of nitroxides using the TP excitation technique, i.e., the concentration jump of nitroxides, is one promising method of exploring the role of these species

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

• Maryam Khalesi,
• Azim Ziyaei Halimehjani and
• Jürgen Martens

Beilstein J. Org. Chem. 2019, 15, 852–857, doi:10.3762/bjoc.15.82

• . cIsolated yield of one of the diastereomers as pure stereoisomer after several recrystallization steps. ORTEP representation of compound (R*,S*)-4a with thermal ellipsoids at 50% probability. Opposite enantiomer is omitted for clarity. The atom numbering does not follow IUPAC nomenclature. Synthesis of

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