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

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

• Grzegorz Mlostoń,
• Katarzyna Urbaniak,
• Paweł Urbaniak,
• Anna Marko,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156

• (for C26H20O2S): 395 (100, [M − 1]−). ORTEP plot [29] of the molecular structure of 4k showing the major conformation of the disordered thiophene ring (50% probability ellipsoids; arbitrary numbering of the atoms). Products of the reactions of thiochalcones 1a and 1b with 1,4-benzoquinone (2a) and of

Synthesis of new tricyclic 5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepine derivatives by [3⁺ + 2]-cycloaddition/rearrangement reactions

• Lin-bo Luan,
• Zi-jie Song,
• Zhi-ming Li and
• Quan-rui Wang

Beilstein J. Org. Chem. 2018, 14, 1826–1833, doi:10.3762/bjoc.14.155

• present synthetic protocol paves the way for further applications in drug-discovery research. Examples of marketed pharmaceutical 1,2,4-triazolobenzodiazepines. Crystal structure of salt 10k. The displacement ellipsoids are drawn at the 30% probability level. Crystal structure of the free base 13e. The

• displacement ellipsoids are drawn at the 30% probability level. Preparation of N-acylated 2,3-dihydro-4(1H)-quinolones 6. Synthesis of α-acetoxyazo compounds 8a–g. Reaction conditions: for synthesis of 8a: 7a (10.42 mmol), PhI(OAc)2 (12.50 mmol), AcOH (10 mL); for synthesis of 8b–g: 7b–g (0.71 mmol), PhI(OAc)2

Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases

• Svetlana O. Kasatkina,
• Ekaterina E. Stepanova,
• Maksim V. Dmitriev,
• Ivan G. Mokrushin and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2018, 14, 1734–1742, doi:10.3762/bjoc.14.147

• under solvent-free conditions. ORTEP drawing of compound 3g (CCDC 1834011) showing thermal ellipsoids at the 30% probability level. ORTEP drawing of compound 3j (CCDC 1834012) showing thermal ellipsoids at the 30% probability level. Thermolysis of five-membered 2,3-dioxoheterocycles resulting in acyl

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

• Mark Kelada,
• John M. D. Walsh,
• Robert W. Devine,
• Patrick McArdle and
• John C. Stephens

Beilstein J. Org. Chem. 2018, 14, 1222–1228, doi:10.3762/bjoc.14.104

• of versatile 5-aminopyrazoles is reported. Bioactive pyrazolo[1,5-a]pyrimidinones. X-ray crystal structure of pyrazolo[1,5-a]pyrimidinone 3m with ellipsoids at 50% probability. Synthesis of 5-aminopyrazoles. Reaction conditions: ketonitrile (2.0 mmol, 1.0 equiv), hydrazine (2.6 mmol, 1.3 equiv), MeOH

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

• Akira Yoshimura,
• Michael T. Shea,
• Cody L. Makitalo,
• Melissa E. Jarvi,
• Gregory T. Rohde,
• Akio Saito,
• Mekhman S. Yusubov and
• Viktor V. Zhdankin

Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

• assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate to good yields. X-ray crystal structure of compound 7a. Ellipsoids are drawn to the 50% probability level. Selected bond lengths and angles: I(1)–C(1) 2.040 (4) Å; I(1)–N(1) 2.184 (4) Å; I

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• substrates through the hydrogels and increased the probability of the reactant to be in contact with the catalyst (Ag NPs). Conclusion In this review we have discussed the utility of supramolecular polymersomes, micelles, dendrimers and nanogels in catalysis. Over the past decades, many groups have

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

• Rebecca Pittkowski and
• Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

• ); 195Pt NMR (CDCl3, 64.52 MHz) δ (ppm) −3383; ESIMS m/z = 688.4 [M + H]+; anal. calcd for C33H36N2O2Pt: C, 57.63; H, 5.28; N, 4.07; found: C, 57.93; H, 5.46; N, 3.82. ORTEP representation of 3. Thermal ellipsoids are drawn at the 50% probability level. Selected bond lengths (Å) and angles (deg): C(1)–Pt(1

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

• Robby Vroemans,
• Fante Bamba,
• Jonas Winters,
• Joice Thomas,
• Jeroen Jacobs,
• Luc Van Meervelt,
• Jubi John and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

• examples. X-ray crystal structure of hydantoin-fused triazolobenzodiazepine 10a. (Displacement ellipsoids are drawn at the 30% probability level.) Retrosynthetic analysis towards 2,5-diketopiperazine fused triazolobenzodiazepine. Ugi 4-CR reaction. Synthesis of diketopiperazine-fused triazolobenzodiazepine

An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

• Longcheng Hong,
• Sebastian Ahles,
• Andreas H. Heindl,
• Gastelle Tiétcha,
• Andrey Petrov,
• Zhenpin Lu,
• Christian Logemann and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2018, 14, 618–625, doi:10.3762/bjoc.14.48

• distilled off from the resulting mixture in vacuo. The residue was purified by column chromatography over SiO2 (ethyl acetate/cyclohexane 1:1) to obtain the product. Time-dependent 1H NMR spectra of the air-exposed complex B. ORTEP drawing (50% probability) of complex B. UV–vis spectrum of complex B was

Carbohydrate inhibitors of cholera toxin

• Vajinder Kumar and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34

• ligand group dissociates from the protein, then the others will continue to make contact between the protein and the inhibitor, thus maintaining a high effective concentration of the dissociated ligand group in the vicinity of the binding site and increasing the probability of rebinding occurring. The