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

• , so that the pure products were only available by crystallization from appropriate solvents, which resulted in lower yields of these products. Single crystal X-ray diffraction analysis of 9-(arylethynyl)benzo[b]quinolizinium derivatives 2a and 2b Single crystals of derivatives 2a and 2b were obtained

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

• Irina A. Mironova,
• Pavel S. Postnikov,
• Rosa Y. Yusubova,
• Akira Yoshimura,
• Thomas Wirth,
• Viktor V. Zhdankin,
• Victor N. Nemykin and
• Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

• -iodobenzenesulfonate with Oxone or sodium periodate in water is reported. The single crystal X-ray diffraction analysis reveals a complex polymeric structure consisting of three units of IBS as potassium salt and one unit of 2-iodoxybenzenesulfonic acid linked together by relatively strong I=O···I intermolecular

• -iodosylbenzenesulfonic acid as confirmed by X-ray diffraction analysis [17]. In the present work, we report the preparation and isolation of IBS (as potassium or sodium salts) and its structural study by X-ray analysis. Furthermore, we have developed a new method for the preparation of the IBS reduced form, 2

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

• Rakesh Puttreddy,
• Ngong Kodiah Beyeh,
• S. Maryamdokht Taimoory,
• Daniel Meister,
• John F. Trant and
• Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

• Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, N9B 3P4, Canada 10.3762/bjoc.14.146 Abstract Host–guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• molecular structure of 4,5-benzotropone (11) was determined by Hata’s group [50]. X-ray diffraction analysis showed that the molecule is approximately planar and the bond alternation in the seven-membered ring and C=O bond length support satisfactory aromaticity. 2.1. Synthesis of 4,5-benzotropone (11

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• pyrenyl–thymine 2 was confirmed by single-crystal X-ray analysis. Crystal structure Crystals of 2 suitable for X-ray diffraction analysis were obtained by slow diffusion of pentane into a chloroform solution of 2. The oak ridge thermal-ellipsoid plot (ORTEP) with the atom labelling scheme is shown in

Enzymatic separation of epimeric 4-C-hydroxymethylated furanosugars: Synthesis of bicyclic nucleosides

• Neha Rana,
• Manish Kumar,
• Vinod Khatri,
• Jyotirmoy Maity and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2017, 13, 2078–2086, doi:10.3762/bjoc.13.205

• , IR spectra and HRMS) analysis. The structure of known compounds 9 [19] and 14 [20] were further confirmed on the basis of comparison of its physical and spectral data with those reported in the literature. The single crystal X-ray diffraction analysis has been performed on compounds 5, 10 and 14 and

Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

• Mario Pérez-Venegas,
• Gloria Reyes-Rangel,
• Adrián Neri,
• Jaime Escalante and
• Eusebio Juaristi

Beilstein J. Org. Chem. 2017, 13, 1728–1734, doi:10.3762/bjoc.13.167

• ); however, the best results continued to be obtained by using the conditions indicated in Table 1, entry 3. To establish the absolute configuration of product 2a, a sample was crystallized to give a suitable single-crystal for X-ray diffraction analysis. The resulting structure showed the R configuration

First total synthesis of kipukasin A

• Chuang Li,
• Haixin Ding,
• Zhizhong Ruan,
• Yirong Zhou and
• Qiang Xiao

Beilstein J. Org. Chem. 2017, 13, 855–862, doi:10.3762/bjoc.13.86

• -isopropylidene-D-ribofuranose (12) with 2-iodobenzoyl chloride (0.9 equiv) gave the corresponding 5-O-benzoyl ester 13 in 80% yield along with a small amount of the 3,5-dibenzoyl ester. The structure of 5-O-benzoyl ester 13 was unambiguously confirmed by X-ray diffraction analysis (Figure 3) [34]. Then

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• with respect to their structural and electronic properties, we herein present some relevant data of the 1,2,4-triazolium-hydrazinides 7. Thus, the molecular structure of 7a in the solid state was determined by X-ray diffraction analysis and is shown in Figure 4. Two symmetrically independent molecules

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

• Ramana Sreenivasa Rao and
• Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

• evidence for cyclized compounds 9b and 10a was supported by single-crystal X-ray diffraction analysis (Figure 3) in addition to IR, NMR and HRMS data. To show the synthetic utility of substituted pyrazinones, we introduce a phenyl group at the C-3 position in pyrazinone derivative 10a. To begin with, the

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• evidences for the structural assignment were sought from X-ray crystallography. Fortunately, we got the single crystals of (±)-5k by slow evaporation of a solution of 5k in hexane/EtOAc, and its molecular structure was confirmed by X-ray diffraction analysis (Figure 3). The 1H and 13C NMR spectra of all the

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• racemates (2a, 2c/2b, 2d; 3a, 3c/3b, 3d) by HPLC–ECD analysis (Figure 1). The planar structure and absolute configuration of the first-eluted stereoisomer of dracocephins A (±)-2a–d was determined by single-crystal X-ray diffraction analysis as (2R,5”S)-2a [2]. The biosynthesis of these flavonoid

Et₃B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

• Ahlem Abidi,
• Yosra Oueslati and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2402–2409, doi:10.3762/bjoc.12.234

• conjugate addition of the β-keto ester carbanion onto the enone moiety (Scheme 2) [50][51]. The structure of the tricyclic compound 6j was elucidated on the basis of X-ray diffraction analysis (Figure 2). In a previous report, Alexakis and co-workers have demonstrated that copper-catalyzed conjugate

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

• Alexei N. Izmest’ev,
• Galina A. Gazieva,
• Natalya V. Sigay,
• Sergei A. Serkov,
• Valentina A. Karnoukhova,
• Vadim V. Kachala,
• Alexander S. Shashkov,
• Igor E. Zanin,
• Angelina N. Kravchenko and
• Nina N. Makhova

Beilstein J. Org. Chem. 2016, 12, 2240–2249, doi:10.3762/bjoc.12.216

• Supporting Information File 1 for full experimental data). Finally, the regio- and stereochemistry of the cycloaddition were confirmed by single crystal X-ray diffraction analysis of compounds 4c (Figure 5), 4e (Figure 6), and 4r (Figure 7) (see Supporting Information Files 2–4). The relative configurations

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• counter and pseudoreference electrodes. Crystals suitable for X-ray diffraction analysis were obtained by the slow diffusion of methanol into a dichloromethane solution. The crystals obtained were dark blue-black in appearance. Single-crystal X-ray diffraction studies were carried out using a Rigaku Rapid

Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

• Sambasivarao Kotha and
• Rama Gunta

Beilstein J. Org. Chem. 2016, 12, 1877–1883, doi:10.3762/bjoc.12.177

• propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules. Keywords: norbornene; propellane derivatives; ring-closing metathesis; single-crystal X-ray diffraction; vicinal

• supported by HRMS data. In addition, the configuration of 1b and 2b were unambiguously determined via single-crystal X-ray diffraction analysis (Figure 4). Based on this data it is clear that the bridgehead allyl groups in the RCM precursor 2b are in endo configuration. Subsequent RCM of diallyl compound 2b

• X-ray diffraction analysis. A control experiment with propyl bromide provided an insight into the reaction mechanism that the bridgehead allylation proceeds through enolization, O-allylation followed by CR and not via carbanion chemistry. This alternative strategy is useful to introduce vicinal

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• then the resulting pH (pHf) was measured. The difference between the initial and final pH values (ΔpH) was plotted against the initial pH. The PZC was represented by the point ΔpH = 0 [32]. X-ray diffraction analysis (XRD) was performed on a Bruker D8 Advance diffractometer using Cu Kα radiation with a

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

• Valeria Corne,
• Ariel M. Sarotti,
• Carmen Ramirez de Arellano,
• Rolando A. Spanevello and
• Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

• the π-stacking interaction also affects the equilibrium kinetics. In order to better understand the conformational studies, a crystal of acrylate 6a suitable for X-ray diffraction analysis was obtained (for further information, see Supporting Information File 1). The crystal structure shows the vinyl

A T-shape diphosphinoborane palladium(0) complex

• Patrick Steinhoff and
• Michael E. Tauchert

Beilstein J. Org. Chem. 2016, 12, 1573–1576, doi:10.3762/bjoc.12.152

• the ligand pointing towards the formation of a bisligand complex (DPB)2Pd [7]. Unlike complex 2 we were unable to form a pyridine adduct complex by treatment of 9 with 10 equiv of pyridine. Single crystals of complex 9 suitable for X-ray diffraction analysis were grown from hexane (Figure 2). The

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

• Bo Yang,
• Chuanye Tao,
• Taofeng Shao,
• Jianxian Gong and
• Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

• products were characterized by 1H NMR, 13C NMR, HRMS spectra and the structure of 1o was further confirmed by X-ray diffraction analysis (see Supporting Information File 1 for details). A possible mechanism for the MCR is proposed in Figure 2. The MCR proceeds through the formation of a protonated imine

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• range of 157.6–216 ppm [34][35]. Single crystal X-ray diffraction studies To obtain additional insight into the coordination and supramolecular properties, suitable single crystals of all the copper complexes were obtained for single-crystal X-ray diffraction analysis. Crystals were grown by slow

• desired product X-ray diffraction analysis Analogously as described in [27], single-crystal X-ray diffraction data were collected at 298(2) K on a Siemens Smart/CCD area-detector or Oxford Diffraction Gemini A Ultra diffractometer with a Mo Kα radiation (λ = 0.71073 Å) by using an ω-2θ scan mode. Unit

• route: imidazolium salt (0.2 mmol) and an excess of copper powder (64 mg, 1.0 mmol) were placed in 3 mL of MeCN to form a heterogeneous mixture solution. After the mixture was stirred at 50 °C for 10 h under air, the solution was filtered through Celite. Single crystals suitable for X-ray diffraction

A modular approach to neutral P,N-ligands: synthesis and coordination chemistry

• Vladislav Vasilenko,
• Torsten Roth,
• Clemens K. Blasius,
• Sebastian N. Intorp,
• Hubert Wadepohl and
• Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 846–853, doi:10.3762/bjoc.12.83

• crystals of [2a-PdCl2] and [5-Pd(2-Me-allyl)]OTf suitable for X-ray diffraction analysis (Figure 6). For an overview of metric parameters of all palladium complexes see Table 3. The solid-state structures of [2a-PdCl2] (Figure 6, left) and its cationic congener [2a-PdCl]2(BF4)2 (Figure 5) show distinct

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

• Štěpán Horník,
• Lucie Červenková Šťastná,
• Petra Cuřínová,
• Jan Sýkora,
• Kateřina Káňová,
• Roman Hrstka,
• Ivana Císařová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75

• acetal with acetic anhydride gave a mixture containing 1,2-oxazoline 41 as the main product (Scheme 5). The structure of oxazoline 41 was confirmed by single crystal X-ray diffraction analysis which also confirmed the retention of configuration during the preceding fluorine introduction. To prevent

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

• M. Fernanda N. N. Carvalho,
• M. João Ferreira,
• Ana S. O. Knittel,
• Maria da Conceição Oliveira,
• João Costa Pessoa,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2016, 12, 732–744, doi:10.3762/bjoc.12.73

• concerning the analytical formulation of 2, its structure remained unclear. In the absence of crystals suitable for single crystal X-ray diffraction analysis, this point was fully clarified by NMR (Supporting Information File 1, Figure S2–S6) and further supported by calculations. The assignment of all

Pyridylidene ligand facilitates gold-catalyzed oxidative C–H arylation of heterocycles

• Kazuhiro Hata,
• Hideto Ito,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2015, 11, 2737–2746, doi:10.3762/bjoc.11.295

• -ray diffraction analysis was obtained by recrystallization from nitrobenzene and pentane. 1H NMR (CDCl3, 600 MHz) δ 8.17 (d, J = 2.1 Hz, 1H), 7.90 (d, J = 2.1 Hz, 1H), 7.29 (td, J = 7.6, 2.7 Hz, 2H), 7.19 (d, J = 7.6 Hz, 2H), 7.16 (d, J = 7.6 Hz, 2H), 7.07 (s, 2H), 2.36 (s, 3H), 2.28 (s, 12H), 2.15 (s

• atmosphere. After stirring at room temperature for 19 h, the reaction mixture was filtered through a pad of Celite®. The filtrate was poured into hexane and the resulting precipitate was collected by filtration to obtain pure AuCl3(PyC) as a white solid (140 mg, 99%). The colorless single crystal used for X