Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles

• Sara Tejera,
• Giada Caniglia,
• Rosa L. Dorta,
• Andrea Favero,
• Javier González-Platas and
• Jesús T. Vázquez

Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282

• /H2O, 1:2, v/v, middle right), 12 (DMSO, bottom left), and 14 (DMSO/H2O, 9:1, v/v, bottom right). ORTEP representation of the molecular structure of compound 12 (trans configuration) obtained from X-ray diffraction data. Crystal packing of compound 12 (trans configuration) in DMSO. Crystal packing of

Preparation of anthracene-based tetraperimidine hexafluorophosphate and selective recognition of chromium(III) ions

• Qing-Xiang Liu,
• Feng Yang,
• Zhi-Xiang Zhao,
• Shao-Cong Yu and
• Yue Ding

Beilstein J. Org. Chem. 2019, 15, 2847–2855, doi:10.3762/bjoc.15.278

• tertiary amine, did not shift discernibly during 1H NMR titration; (2) if the tertiary amine groups coordinated to one Cr3+ ion each, a 1:2 binding mode would have been determined for 3⋅Cr3+; and (3) from the molecular structure of 3, due to the distance, it is spatially impossible that one Cr3+ ion is

• ]. SHELXS was used to solve the structure of 3 [57]. Other crystallographic data are shown in Supporting Information File 1, Table S1. View of the molecular structure of the cationic moiety of 3 in the crystal. Selected bond angles and lengths are N(2)–C(3)–N(1): 125.2(3)°; N(5)–C(18)–N(4): 124.3(4)°; C(3

Photoreversible stretching of a BAPTA chelator marshalling Ca²⁺-binding in aqueous media

• Aurélien Ducrot,
• Arnaud Tron,
• Robin Bofinger,
• Ingrid Sanz Beguer,
• Jean-Luc Pozzo and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811, doi:10.3762/bjoc.15.273

• the absorption at a certain wavelength. The x-intercept gives the log Kd. Molecular modelling: The molecular structure of 1E·Ca2+ and 1Z·Ca2+ were built with AMPAC 10.1. A geometry optimization was performed by energy minimization using the PM6 method; solvation was not considered. Synthetic

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• ]): 557 (6000); quantum yield (CH2Cl2) Φf = < 0.01; Anal. calcd for C25H22N2O4 (414.2): C, 72.45; H, 5.35; N, 6.76; found: C, 71.97; H, 5.45; N, 6.52. Molecular structure of 1H-pyridine 5a (50% thermal ellipsoids), showing the intramolecular N–H···O bond as dashed orange line. H-bond details N1–H 0.90(2

AgNTf₂-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

• Ziping Cao,
• Jiekun Zhu,
• Li Liu,
• Yuanling Pang,
• Laijin Tian,
• Xuejun Sun and
• Xin Meng

Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255

• %) in DCE (2.0 mL) at 80 °C, unless otherwise noted. Isolated yields are provided. Scope with regard to the 5-aminoisoxazole 8 (see Figure 2). aReaction conditions: 2.0 equiv of 8e, 100 °C. Molecular structure in the solid state of compound 10ad. Two modes of reactions of alkynes by silver catalysis

Probing of local polarity in poly(methyl methacrylate) with the charge transfer transition in Nile red

• Aydan Yadigarli,
• Qimeng Song,
• Sergey I. Druzhinin and
• Holger Schönherr

Beilstein J. Org. Chem. 2019, 15, 2552–2562, doi:10.3762/bjoc.15.248

• ., USA) according to published protocols [2][3]. Molecular structure of Nile red (NR). Fluorescence (a) and absorption (b) spectra of NR in solvents of different polarity at 25 °C. The solvent marks are hexane for n-hexane, CHCl3 for chloroform, EtOAc for ethyl acetate, CH2Cl2 for dichloromethane, (CH2Cl

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

• Celine Bittner,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

• 1b crystallises in the monoclinic space group P21/c. The asymmetric unit for the molecular structure of 1b shows only half a molecule with the other half being generated through an inversion centre located on the iron atom. For both structures, the iron-centroid (Fe–Ct) distances of 1.6947(12) Å (Fe

• cyclopentadienyl rings should disclose alternate positions as well, however, the central position of Fe’ prevents such observation. Nevertheless, it should be taken into account that the discussed structural parameters for 1a should not be viewed representative for the molecular structure of 1a as a result of the

• . Crystallisation from a saturated solution of DCM layered with hexanes finally yielded 96% of the ferrocenium compound 4 as blue needles, which were suitable for X-ray diffraction analysis (Scheme 2). An ORTEP diagram of the molecular structure of 4 can be seen in Figure 8. The oxidized ferrocenophane 4

Photochromic diarylethene ligands featuring 2-(imidazol-2-yl)pyridine coordination site and their iron(II) complexes

• Andrey G. Lvov,
• Max Mörtel,
• Anton V. Yadykov,
• Frank W. Heinemann,
• Valerii Z. Shirinian and
• Marat M. Khusniyarov

Beilstein J. Org. Chem. 2019, 15, 2428–2437, doi:10.3762/bjoc.15.235

• successfully applied for the synthesis of a new family of photochromic ligands. The structures of the synthesized diarylethene-based ligands 3, 4, 6, and 7 were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry. The molecular structure of 6 was additionally confirmed by X-ray crystallography. In

• irradiation (313 nm, toluene, c = 3.4 × 10−5 M). Inset: fatigue resistance upon multiple subsequent irradiation with UV (365 nm) and visible light (green LED) in acetonitrile. Molecular structure of complexes 8 (top) and 9 (bottom) at 100 K. The H atoms are omitted for clarity; the thermal ellipsoids are

Effect of ring size on photoisomerization properties of stiff stilbene macrocycles

• Sandra Olsson,
• Óscar Benito Pérez,
• Magnus Blom and
• Adolf Gogoll

Beilstein J. Org. Chem. 2019, 15, 2408–2418, doi:10.3762/bjoc.15.233

• ]. For example, each CH2 signal is generated by four CH2 protons which are chemically equivalent in the averaged chemical structure (≈ the 2D molecular structure) but not in individual conformers. They cannot be distinguished on the NMR timescale. Therefore, the calculated distances rave, being averages

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• ); EIMS (70 eV, m/z (%)): 295 (15) [M+], 294 (100), 277 (12), 276 (60), 180 (25); Anal. calcd for С9Н12F3N5O3 (295.23): C, 36.62; H, 4.10; F, 19.31; N, 23.72%; found: C, 36.53; H, 4.21; F, 19.20; N, 23.84%. Molecular structure of 9a according to X-ray data. Displacement ellipsoids are shown at the 50

Excited state dynamics for visible-light sensitization of a photochromic benzil-subsituted phenoxyl-imidazolyl radical complex

• Yoichi Kobayashi,
• Yukie Mamiya,
• Katsuya Mutoh,
• Hikaru Sotome,
• Masafumi Koga,
• Hiroshi Miyasaka and
• Jiro Abe

Beilstein J. Org. Chem. 2019, 15, 2369–2379, doi:10.3762/bjoc.15.229

• photoswitch molecules, the phenoxyl-imidazolyl radical complex (PIC) is a recently developed thermally reversible photochromic molecule whose thermal back reaction can be tuned from tens of nanoseconds to tens of seconds by rational design of the molecular structure. While the wide range of tunability of the

Characterization of two new degradation products of atorvastatin calcium formed upon treatment with strong acids

• Jürgen Krauß,
• Monika Klimt,
• Markus Luber,
• Peter Mayer and
• Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2085–2091, doi:10.3762/bjoc.15.206

• treatment with acids: lactone 2, dehydrated lactone 3, α,β-unsaturated carboxylic acid 4, and carboxylic acid 5 (resulting from postulated anilide hydrolysis). Top: Molecular structure of artefact 6. Shown here is the molecular structure of one of three independent molecules in 6 drawn at the 50% ellipsoid

• probability level. Bottom: Molecular structure of artefact 7 (drawn at the 50% ellipsoid probability level). Separation of atorvastatin (1; retention time: 5.8 min) from the four decomposition products 2 (retention time: 9.2 min), 3 (retention time: 15.6 min), 6 (retention time: 21.4 min) and 7 (retention

Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs₂CO₃-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

• Mio Matsumura,
• Yuki Kitamura,
• Arisa Yamauchi,
• Yoshitaka Kanazawa,
• Yuki Murata,
• Tadashi Hyodo,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2019, 15, 2029–2035, doi:10.3762/bjoc.15.199

• group having bromine to generate the tetracyclic target molecule. Conclusion Benzo[d]imidazo[2,1-b]benzoselenoazoles were prepared via Cs2CO3-mediated tandem cyclization followed by reaction of 1-(2-bromoaryl)benzimidazoles with Se powder without a transition metal catalyst. The molecular structure of

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• , 1325, 1228, 1113, 1066. HRMS-APCI: [M − H]− calcd for C63H41N21O15F9, 1502.2953; found, 1502.2972; anal. calcd for C63H42F9N21O15·H2O: C, 49.71; H, 2.91; N, 19.32. found: C, 49.42; H, 3.04; N, 19.01. X-ray molecular structure of 3a (CCDC 1913907) with side (left) and top (right) views. All solvent

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

• Xiao Xie,
• Michela Zuffo,
• Marie-Paule Teulade-Fichou and
• Anton Granzhan

Beilstein J. Org. Chem. 2019, 15, 1872–1889, doi:10.3762/bjoc.15.183

• common feature of mono- and distyryl dyes, including long-known mono-styryl dyes used as mitochondrial probes or protein stains. However, the magnitude of the G4-induced “light-up” effect varies drastically, as a function of both the molecular structure of the dyes and the nature or topology of G4

• to the molecular structure of dyes, it may be concluded that lipophilic substituents (1c, 1d, 1ð, 1y, 1Þ) and/or π-expanded heterocyclic cores (9a, 10a, 12a, 14p) promote the dye aggregation, but the nature of the resulting aggregate (H vs J) is unpredictable. Conversely, small or hydrophilic

• solvents (MeOH, DMSO) and in aqueous buffer, as assessed by visual inspection of the respective solutions. In non-aggregating conditions, the influence of the molecular structure of the dyes on their absorption bands can be clearly observed. Thus, when Ar contains poor electron-donating substituents (1g–1j

Cyclobutane dication, (CH₂)₄²⁺: a model for a two-electron four-center (2e-4c) Woodward–Hoffmann frozen transition state

• G. K. Surya Prakash and
• Golam Rasul

Beilstein J. Org. Chem. 2019, 15, 1475–1479, doi:10.3762/bjoc.15.148

• . This type of bonding could occur in rigid frameworks such as in 1,3-dehydro-5,7-adamantanediyl dication (iii) [7] and pagodane dication (iv) [8]. The question is can a 2e-4c bond exist in a molecular structure involving four atoms without any rigid frameworks such as in the diprotonated hydrogen (H42

One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

• Christina Görgen,
• Katharina Boden,
• Guido J. Reiss,
• Walter Frank and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

• intermediate 5a could be a 1,5-diacylpyrazole. However, upon performing the terminal cyclization step starting from 1,4-diphenylbut-3-yne-1,2-dione (3a) and Boc-hydrazine (4a) under identical conditions 1-Boc-5-benzoyl-5-hydroxypyrazoline was isolated in 83% yield (Scheme 3). The molecular structure was

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

• Andrew T. King,
• Hugh G. Hiscocks,
• Lidia Matesic,
• Mohan Bhadbhade,
• Roger Bishop and
• Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

• (H···H = 2.48 Å) there is also a linear C6D–H6D···H6D–C6D close contact (H···H = 2.37 Å) around a further inversion centre. These two motifs alternate along the a axis to produce infinite hydrocarbon tapes with inversion centres separated by a/2 (Figure 6). The molecular structure of 8 precludes

Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones

• Alexander N. Reznikov,
• Anastasiya E. Sibiryakova,
• Marat R. Baimuratov,
• Eugene V. Golovin,
• Victor B. Rybakov and
• Yuri N. Klimochkin

Beilstein J. Org. Chem. 2019, 15, 1289–1297, doi:10.3762/bjoc.15.127

• suitable for X-ray analysis were obtained for compound 8d (which is formed as an individual diastereomer). This made it possible to determine its absolute (2R,3S)-configuration, as well as to assign the absolute configuration for the other compounds obtained. The molecular structure of compound 8d is shown

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• 70 °C) and a small focused library of 23 Ugi products was created. The target compounds containing two pharmacophore pyrazolopyridine and peptidomimetic moieties were screened for their antibacterial activity and demonstrated weak antibacterial effect. Molecular structure of N-(2-(tert-butylamino)-1

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

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

Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• present in the molecular structure. Combined with merits of host molecules and electrospun nanofibers, the supramolecular host functionalized nanofibers have been widely reported in recent years as efficient molecular filters and absorbent for the removal of hazardous chemicals or polluting substances. A

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

• Leon Buschbeck,
• Aleksandra Markovic,
• Gunther Wittstock and
• Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

• ), which is expected from the molecular structure of compounds 3 and 7, may be caused by residual adsorbed water that also causes an O 1s component at 533.0–533.5 eV [57][58]. The main doublet in the S 2p spectra of both monolayers at 161.8 eV corresponds to sulfur bound to gold [59]. Although, S 2p

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