Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

• Masahiro Kako,
• Masato Kai,
• Masanori Yasui,
• Michio Yamada,
• Yutaka Maeda and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

• 305-8577, Japan 10.3762/bjoc.20.100 Abstract The addition reaction of C60 with silylene 1, a silicon analog of carbene, yielded the corresponding bis-adduct 3. The structure of 3 was determined by single-crystal X-ray structure analysis, representing the first example of a crystal structure of a

• ions of 3. Finally, the structure of 3 was established by single-crystal X-ray structure analysis. The ORTEP diagram of 3 is presented in Figure 5 with the selected bond lengths and angles collected in Table 1. The cage C–C bond lengths of the addition sites are C1–C9: 1.623(2) Å and C21–C40: 1.6282(19

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

• Matthias R. Steiner,
• Max Schmallegger,
• Larissa Donner,
• Johann A. Hlina,
• Christoph Marschner,
• Judith Baumgartner and
• Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

• product of interest 2a. Compound 2a was identified by a combination of NMR spectroscopic methods and single-crystal X-ray structure analysis (vide infra) as the zwitterionic phospha-Michael adduct of 1 and acrylonitrile, formally stabilized by proton transfer from the phenol group to the initially formed

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• at 90–100 °C was reported to give 3β-azidocholest-5-ene [10]. Comparing the respective NMR data with the published ones [12] revealed a difference of about 0.6 ppm for the chemical shift of H3 suggesting a miss-assignment [23]. This assumption was confirmed by the X-ray structure analysis of single

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

• Jolita Bruzgulienė,
• Greta Račkauskienė,
• Aurimas Bieliauskas,
• Vaida Milišiūnaitė,
• Miglė Dagilienė,
• Gita Matulevičiūtė,
• Vytas Martynaitis,
• Sonata Krikštolaitytė,
• Frank A. Sløk and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

• analysis, 1H, 13C, and 15N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data. Keywords: β-enamino ketoesters; heterocyclic amino acids; 15N-labeled 1,2-oxazole; NMR (1H; 13C; 15N); 1,2-oxazole (isoxazole); X-ray structure analysis; Introduction 1,2-Oxazoles (isoxazoles) constitute an

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• were characterized by 1H NMR, 13C NMR, HRMS, and 19F NMR (5b, 5c and 5h) spectroscopy wherever applicable. The structures of compounds 3, 5c and 7b were unambiguously confirmed by single crystal X-ray analysis diffraction method. Single crystal X-ray structure analysis supported the formation of the

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• -Performance LC-MS (electrospray ionization quadrupole time-of-flight) spectrometer. X-ray structure analysis was carried out at a Bruker KAPPA APEXII single crystal X-ray diffractometer. Melting points (mp) are uncorrected and were measured on a Veego melting point apparatus (capillary method). Analytical

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• quantitative yield [47]. Single crystals of intermediate thienopyrrole 25 were obtained by slow evaporation of a chloroform solution and an X-ray structure analysis was performed. Structural details and packing motifs of the molecule are described in Supporting Information File 1. Alkylation to N-propyl

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

• Thomas Schneider,
• Michael Keim,
• Bianca Seitz and
• Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

• = −46.76 ppm, a value quite different from those of products 12 and 13) could finally be isolated in modest yield and was identified by an X-ray structure analysis as the CF3-substituted fulvene 19 (Scheme 7). A reaction pathway leading to fulvene 19 is proposed in Scheme 8. It begins with the formal [2

Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes

• Zeguo Fang,
• Nawaf Al-Maharik,
• Peer Kirsch,
• Matthias Bremer,
• Alexandra M. Z. Slawin and
• David O’Hagan

Beilstein J. Org. Chem. 2020, 16, 674–680, doi:10.3762/bjoc.16.65

• isomer 11b for subsequent analysis. Stereoisomer 11a was a crystalline solid and a suitable crystal was subject to X-ray structure analysis and the structure is shown in Scheme 4. In this way the stereochemistry of 11a and 11b could be confirmed unambiguously. Evaluation of liquid crystal candidates 8

Indium-mediated C-allylation of melibiose

• Christian Denner,
• Manuel Gintner,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2019, 15, 2458–2464, doi:10.3762/bjoc.15.238

• conversion (98%) was obtained by employing indium as the metal species, a solvent mixture of ethanol/water 4:1 (v/v), at a temperature of 65 °C under vigorous stirring. The resulting epimeric forms were isolated and the stereochemical outcome was determined via X-ray structure analysis of the per-O

Synthesis of acremines A, B and F and studies on the bisacremines

• Nils Winter and
• Dirk Trauner

Beilstein J. Org. Chem. 2019, 15, 2271–2276, doi:10.3762/bjoc.15.219

• 16 (CCDC 1854563) and 17 (CCDC 1854564) are available free from charge on https://www.ccdc.cam.ac.uk/structures/). Supporting Information File 296: Experimental part. Acknowledgements The authors thank Dr. Peter Mayer for X-ray structure analysis. Additionally, we acknowledge the Deutsche

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

• Arnault Heynderickx,
• Sébastien Nénon,
• Olivier Siri,
• Vladimir Lokshin and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

• led to variation of its electron donor/acceptor capability that allowed fine-tuning the absorption properties. The propensity of these compounds and a number of its derivatives to form infinite chains involving >N–H···N= and >N–H···Hal−···N+ atoms is demonstrated by X-ray structure analysis. The DFT

• (Figure 3). At the same time, the geometry optimized structure of 6a exhibits much greater torsion angles of 6.23 and 2.28 degrees. The X-ray structure analysis of 7a confirms that the methylation occurs at the N4 atom to form the respective cation (Figure 4). Examination of the bond distances revealed a

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• different spectroscopic techniques, 1H NMR, 13C NMR, IR and HRMS. In addition, one of the compounds, 4d, was also examined by single crystal X-ray structure analysis (Figure 5). Mechanistic pathway A probable mechanism is portrayed in Scheme 3 including the role of the BATA-MC nanoreactor. The nanoreactor

Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif

• Andrea Rodil,
• Alexandra M. Z. Slawin,
• Nawaf Al-Maharik,
• Ren Tomita and
• David O’Hagan

Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144

• of sulfoxide 7 was also confirmed by X-ray structure analysis. The incubation of 4 in C. elegans, and then HPLC purification, was repeated three times all with very similar results. These incubations showed full conversion into the metabolites, and no starting thioether 4 was observed by NMR or HPLC

• Spectrometer, operating in positive and negative mode, from solutions of the analyte in methanol or acetonitrile. The X-ray structure analysis of 7 (CCDC deposition code 1911894) was obtained using a Rigaku XtaLAB P200 diffractometer, using multi-layer mirror monochromed Mo Kα radiation. Structures of

• confirmed by X-ray structure analysis. Putative pathways for (α,α-difluoroethyl)(4-methoxyphenyl)sulfane (4) metabolism. C. elegans incubation of 5. Ratios are the average of three incubations. Incubation (four times) of oxygen ether 14 with C. elegans, gave 4-acetoxyphenol (15) as the major metabolite. On

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• starting material, but also ring fusion to selenophene was achieved by Cu-catalyzed C–Se cross-coupling reaction [28]. The detailed geometric structure and the packing behaviour in the solid state of triacenes 2–4 have been elucidated by single crystal X-ray structure analysis and X-ray diffraction on

• accordance with data for selenophene compared to thiophene [35]. Single crystal X-ray structure analysis Single crystals of heterotriacenes DTS 2, DST 3, and DSS 4 suitable for X-ray structure analysis were obtained and details of the refinements are summarized in Tables S1-S3 (Supporting Information File 1

• ). X-ray structure analysis of DTT 1 was already published by Brédas et al. [36][37]. Single crystals of DTS 2 and DSS 4 as very thin crystalline needles were obtainned by careful sublimation. Both heterotriacenes crystallized in the monoclinic space group P21/c with 18 molecules in the unit cell (DTS

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

• to spectroscopic assignment the structure of 6a has now been corroborated by an X-ray structure analysis showing infinite chains of molecules 6a formed by intermolecular hydrogen bonding between the pyrazole N1 and the carbonyl O1 (Figure 3) [53]. The first assumption was that the tentative

• additionally corroborated by X-ray structure analysis showing that the assignment of intermediate 5a was not a fully unsaturated pyrazole (Figure 4) [53]. Therefore, we set out to optimize the one-pot synthesis of 1,5-diacyl-5-hydroxypyrazolines by choosing the model reaction of phenylglyoxylic acid (1a

• analyses. Additionally, the structure was corroborated by an X-ray structure analysis of compound 5r showing dimers held together by inter- and intramolecular hydrogen bonding (Figure 5) [53]. The three-component synthesis allows addressing three points of diversity and especially for the hydrazide

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

• Amrita Das,
• Mitasree Maity,
• Simon Malcherek,
• Burkhard König and
• Julia Rehbein

Beilstein J. Org. Chem. 2018, 14, 2520–2528, doi:10.3762/bjoc.14.228

• the limit of the scope of the method. The substrate scope is shown in Scheme 3. The structures of compounds 3a, 3d, 3e and 3i in the solid state were determined by X-ray structure analysis (Figure 2). We performed various control experiments to support the proposed reaction mechanism, which is shown

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

• Information File 214: X-ray structure analysis data for 3ca (CCDC-1845323). Acknowledgements This work was supported by the Russian Science Foundation (18-13-00027).

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

• interactions in the context of structure formation in R3Bi compounds (Bi···Bi contacts vary between 4.015 and 4.059 Å) [63]. (C6H4-OMe-4)3Bi (3) (C6H4-OMe-4)3Bi (3) crystallized from CHCl3 in the form of colorless cube-shaped or block-shaped crystals which were suitable for single crystal X-ray structure

• analysis. Compound 3 crystallizes in the trigonal space group (Figure 6). While our work was in progress, Gagnon and co-workers reported the crystal structure of 3, which exhibits very similar lattice parameters [64]. However, the packing structure has not been discussed in detail and thus its description

An unusual thionyl chloride-promoted C−C bond formation to obtain 4,4'-bipyrazolones

• Gernot A. Eller,
• Gytė Vilkauskaitė,
• Algirdas Šačkus,
• Vytas Martynaitis,
• Ashenafi Damtew Mamuye,
• Vittorio Pace and
• Wolfgang Holzer

Beilstein J. Org. Chem. 2018, 14, 1287–1292, doi:10.3762/bjoc.14.110

• prepared. Moreover, the structure of a representative 5,5'-dioxo-4,4'-bipyrazole-4,4'-dicarboxylate was confirmed by X-ray crystal structure analysis. Keywords: dimerization; NMR (1H; 13C; 15N); pyrazolones; thionyl chloride; X-ray structure analysis; Introduction Many biologically active substances

Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations

• Koichi Mitsudo,
• Junya Yamamoto,
• Tomoya Akagi,
• Atsuhiro Yamashita,
• Masahiro Haisa,
• Kazuki Yoshioka,
• Hiroki Mandai,
• Koji Ueoka,
• Christian Hempel,
• Jun-ichi Yoshida and
• Seiji Suga

Beilstein J. Org. Chem. 2018, 14, 1192–1202, doi:10.3762/bjoc.14.100

• –C6, and NMR spectra of all new compounds and C1–C6. Supporting Information File 156: X-ray structure analysis data for 1a (CCDC-1813600), 1b (CCDC-1813582), 1d (CCDC-1813594), 1e (CCDC-1813595), 1f (CCDC-1813596). These data can be obtained free of charge from The Cambridge Crystallographic Data

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

• ; H, 4.87; N, 17.80; found: C, 73.05; H, 5.09; N, 17.59. Single-crystal X-ray structure analysis A good quality single-crystal of 2 was selected for the X-ray diffraction experiments at T = 100(2) K. Diffraction data were collected on an Agilent Technologies SuperNova Dual Source diffractometer with

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

• Matthias Wünsch,
• David Schröder,
• Tanja Fröhr,
• Lisa Teichmann,
• Sebastian Hedwig,
• Nils Janson,
• Clara Belu,
• Jasmin Simon,
• Shari Heidemeyer,
• Philipp Holtkamp,
• Jens Rudlof,
• Lennard Klemme,
• Alessa Hinzmann,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240

• Kuduk et al. [96], remained unsuccessful. The (S)-configuration of the newly generated chiral center of amine 10k was determined by X-ray structure analysis (Figure 7), suggesting two possible transition states for the ligand transfer. Whereas transition state TII requires only one equivalent of AlMe3

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• after purification by column chromatography shows no traces of copper in the ESR spectrum (Supporting Information File 1, Figure S21). X-ray crystal structure analysis Single-crystal X-ray structure analysis was performed for all products. It provided clear identification of the novel triazole

• 5–8 suitable for single crystal X-ray structure analysis were obtained at room temperature by partial evaporation of the solvent from the mixture of dichloromethane and methanol. Data for 5–7 were collected at 295 K on a Oxford Diffraction Xcalibur2 diffractometer with a Sapphire 3 CCD detector