Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• ) was synthesized via consecutive Suzuki coupling and Scholl reaction in a total yield of 77%. The synthesis, molecular structures, nomenclature, and synthetic yields of all compounds are shown in general Scheme 1. All prepared molecules were fully characterized by NMR (1H, 19F and 13C), HRMS, and CHN

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• of ceratinadin G (1) and psammaplysin F (2). Selected 2D NMR correlations for ceratinadin G (1). ECD spectra of ceratinadin G (1) and psammaplysin F (2) in MeOH. 1H and 13C NMR data of ceratinadin G (1) in methanol-d4. Supporting Information Supporting Information File 46: 1H NMR, 13C NMR, 1H-1H

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole

• Baris Temelli and
• Pinar Kapci

Beilstein J. Org. Chem. 2022, 18, 1403–1409, doi:10.3762/bjoc.18.145

• , which is an acid-catalyzed rearrangement of the substituent in intermediates of the condensation reaction. The structures of the meso-pyrrole substituted corroles were identified by using 1H NMR, 1H,1H-COSY NMR and HRMS techniques (see Supporting Information File 1). The 1H NMR spectrum of 2a is shown

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

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

• Sandeep Kumar,
• Jyotirmoy Maity,
• Banty Kumar,
• Sumit Kumar and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

• , 13C NMR, 1H,1H-COSY NMR, 1H,13C-HETCOR NMR, NOESY NMR and HRMS) data analysis. The structures of known compounds 11 and 17 were further confirmed by comparison of their physical and spectral data with those reported in literature [28]. Conclusion The efficiency of Lipozyme® TL IM was discovered for

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• hoshinoamide A. Hindered peptide coupling: conditions and yields. Supporting Information Supporting Information File 278: NMR (1H NMR and 13C NMR) spectra of compounds 2−8, and comparison of the spectral data of natural and synthetic hoshinoamide A. Acknowledgements The authors also sincerely thank Mr

Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

• Takashi Yamazaki,
• Yoh Nakajima,
• Minato Iida and
• Tomoko Kawasaki-Takasuka

Beilstein J. Org. Chem. 2021, 17, 132–138, doi:10.3762/bjoc.17.14

• . The crude mixture proved to be substantially pure, and thus 2c and 2d afforded appropriate analytical data, including NMR (1H, 13C, and 19F), IR, as well as high-resolution MS data. This process allowed us to obtain the required ynones 2 as long as the residue R was aromatic, while with an aliphatic

Particle size effect in the mechanically assisted synthesis of β-cyclodextrin mesitylene sulfonate

• Stéphane Menuel,
• Sébastien Saitzek,
• Eric Monflier and
• Frédéric Hapiot

Beilstein J. Org. Chem. 2020, 16, 2598–2606, doi:10.3762/bjoc.16.211

• throughout the experiments. NMR 1H NMR spectra were recorded on a 300 MHz Bruker Avance III HD spectrometer using D2O (99.92% isotopic purity, Eurisotop) as the solvent. Sampling at several positions in the jar (bulk, powder stuck on the jar or the ball surface) gave comparable results. Generally, the

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

• . Supporting Information Supporting Information File 533: Experimental procedures, NMR (1H, 13C, 19F) and IR spectra of synthesized compounds. Supporting Information File 534: Crystal and structure refinement data for compounds 11, 12c, 12d and 19. Acknowledgements We thank Bernhard Müller for the X-ray data

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• performed in the CESAMO analytical facilities (Bordeaux, France). NMR: 1H and 13C NMR spectra were recorded using a Bruker Avance 300 or a Bruker Avance III 600 spectrometer. Chemical shifts were reported in ppm and referenced to the residual solvent peaks. NMR chemical shifts (δ) were reported in parts per

The McKenna reaction – avoiding side reactions in phosphonate deprotection

• Katarzyna Justyna,
• Joanna Małolepsza,
• Damian Kusy,
• Waldemar Maniukiewicz and
• Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

• the reaction between compound 12, phosphonoacetates 8 and BTMS.a Studies on the reactivity of 13 in the presence of BTMS.a The stability of compounds 8/9 during the McKenna reaction.a,b. Supporting Information Supporting Information File 52: Synthesis of starting materials, copies of 31P NMR, 1H NMR

Experimental and computational electrochemistry of quinazolinespirohexadienone molecular switches – differential electrochromic vs photochromic behavior

• Eric W. Webb,
• Jonathan P. Moerdyk,
• Kyndra B. Sluiter,
• Benjamin J. Pollock,
• Amy L. Speelman,
• Eugene J. Lynch,
• William F. Polik and
• Jason G. Gillmore

Beilstein J. Org. Chem. 2019, 15, 2473–2485, doi:10.3762/bjoc.15.240

• chemical oxidant (benzoquinone) added to complete the reduction of the dianion to the LW isomer. NMR spectroscopy was performed on samples 5 mm NMR tubes (Wilmad) made of clear quartz (photolyzed samples) or amber pyrex (dark samples) on a Varian Mercury or Bruker AvanceIII 400 MHz NMR. 1H NMR experiments

Selective detection of DABCO using a supramolecular interconversion as fluorescence reporter

• Indrajit Paul,
• Debabrata Samanta,
• Sudhakar Gaikwad and
• Michael Schmittel

Beilstein J. Org. Chem. 2019, 15, 1371–1378, doi:10.3762/bjoc.15.137

• in Scheme 1. Therefore, ligands 1 and 2 were synthesized by a palladium-catalyzed Sonogashira coupling reaction (Supporting Information File 1). All compounds were fully characterized by 1H NMR, 1H,1H-COSY, UV–vis, ESIMS and elemental analysis (Supporting Information File 1). Subsequently, we

• prepared the supramolecular rectangle 5 and sandwich complex 6. At first, ligands 1, 2, and [Cu(CH3CN)4]PF6 (1:1:2) were mixed in CD2Cl2 immediately giving rise to rectangle 5 at room temperature. The clear red complex was characterized by ESIMS, 1H NMR, 1H,1H COSY, UV–vis and by elemental analysis

Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

• Fangfang Pan,
• Mohadeseh Dashti,
• Michael R. Reynolds,
• Kari Rissanen,
• John F. Trant and
• Ngong Kodiah Beyeh

Beilstein J. Org. Chem. 2019, 15, 947–954, doi:10.3762/bjoc.15.91

• evidence from 19F NMR, 1H NMR showed small changes of the –OH and –NH2 signals of 1, attributed to the formation of HB and XB in solution (Figure 5 and Figure S4 in Supporting Information File 1). In the presence of the guests (MeOH and MeCN), 1H NMR reveal significant complexation-induced shielding of the

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• via a 13C magic angle spinning nuclear magnetic resonance spectroscopy (MAS NMR) 1H-13C-CP experiment. An overall information of the compound is obtained by attenuated total reflection infrared spectroscopy (ATR-IR). Figure 1 shows the results of the characterization exemplarily for the fullerenol

• with ESIMS, TGA and MAS NMR. These compounds can serve as precursors for further modified fullerenols or as true surfactants. Characterization of fullerenol amphiphile with substituent 1. a) ESIMS in positive mode, molecular ion peak marked with circle, b) TGA under nitrogen with 5 K/min, c) MAS-NMR

• (1H-13C-CP) with structure of substituent, d) ATR–IR. Reaction scheme for the one-pot reaction of C60Cl6 to produce Janus-type fullerenols (OH)19+/−3C60(HNR)5. Scope of the reaction and isolated yields. Supporting Information Supporting Information File 358: General methods and characterization data

Non-metal-templated approaches to bis(borane) derivatives of macrocyclic dibridgehead diphosphines via alkene metathesis

• Tobias Fiedler,
• Michał Barbasiewicz,
• Michael Stollenz and
• John A. Gladysz

Beilstein J. Org. Chem. 2018, 14, 2354–2365, doi:10.3762/bjoc.14.211

• NMR (1H, 31P{1H}, 13C{1H}; always CDCl3) and IR spectroscopy, mass spectrometry, and microanalysis, as summarized in the experimental section. The 13C{1H} NMR spectra proved to be most diagnostic of structure, and were analyzed in detail. The 31P{1H} NMR spectra were all very similar (broad apparent

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

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• hybrid compound 4g in 17% yield (Scheme 3). The structures of the hybrid compounds were identified by using 1H NMR, 13C NMR, 1H,1H-COSY NMR and HRMS techniques (see Supporting Information File 1). The 1H NMR spectrum of 4a is shown in Figure 1. As reported for similar dimeric porphyrin systems, one of

Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity

• Tathagata Mukherjee,
• Soumik Biswas,
• Andreas Ehnbom,
• Subrata K. Ghosh,
• Ibrahim El-Zoghbi,
• Nattamai Bhuvanesh,
• Hassan S. Bazzi and
• John A. Gladysz

Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246

• analogous reaction at room temperature gave Rf15CH2OTf in 22% yield. The triflates were white solids with some solubility in acetone. They were characterized by IR and NMR (1H, 13C{1H}, 19F{1H}) spectroscopy and microanalyses as summarized in the experimental section. The triflates were treated with NaI in

Synthesis of tetrasubstituted pyrazoles containing pyridinyl substituents

• Josef Jansa,
• Ramona Schmidt,
• Ashenafi Damtew Mamuye,
• Laura Castoldi,
• Alexander Roller,
• Vittorio Pace and
• Wolfgang Holzer

Beilstein J. Org. Chem. 2017, 13, 895–902, doi:10.3762/bjoc.13.90

• condensation product was confirmed by crystal structure analysis. Keywords: Negishi coupling; NMR (1H; 13C; 15N); pyrazole; pyridine; X-ray structure analysis; Introduction The pyrazole nucleus is a frequently occurring motif in many pharmaceuticals [1][2] and biologically active compounds [3][4

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• discussed in the following of this work represent an example. Results and Discussion Solid-state NMR 1H MAS NMR spectroscopy 1H high-resolution spectra of small organic molecules, characterised by the isotropic chemical shift and J couplings, are easily obtained in solution. By contrast, for rigid solids

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• % yield). The number of HEE groups in 6 was determined to be 226.6 by comparing the 1H NMR peak area between 3.12 ppm (-NH-CH2-CH2-O- of HEE group) and 4.7–5.2 ppm (H1 proton of α-CD). The Mn of 6 was determined to be 79,800 from the 1H NMR. 1H NMR (500 MHz, DMSO-d6) δ 3.12 (m, -NH-CH2-CH2- of HEE group

Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

• Reji Thomas and
• Nobuyuki Tamaoki

Beilstein J. Org. Chem. 2016, 12, 2211–2215, doi:10.3762/bjoc.12.212

• references. Experimental All solvents and chemicals were obtained from commercial sources and used without further purification, unless otherwise stated. NMR (1H and 13C) spectra were recorded with a JEOL ECX 400 spectrometer using tetramethylsilane as an internal standard. Matrix-assisted laser desorption

Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation

• Tai Nguyen Van,
• Audrey Hospital,
• Corinne Lionne,
• Lars P. Jordheim,
• Charles Dumontet,
• Christian Périgaud,
• Laurent Chaloin and
• Suzanne Peyrottes

Beilstein J. Org. Chem. 2016, 12, 1476–1486, doi:10.3762/bjoc.12.144

• acids. Thus, nucleoside phosphonate analogues 1a–q (Scheme 2) were isolated as their sodium salts with yields ranging from 21 to 77% over three steps. Structures of all final compounds were unambiguously confirmed on the basis of NMR (1H, 13C and 31P) and MS (MS and HRMS) data analysis (see Supporting

On the mechanism of imine elimination from Fischer tungsten carbene complexes

• Philipp Veit,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2016, 12, 1322–1333, doi:10.3762/bjoc.12.125

• C21H19NFe2. A tiny peak cluster at m/z = 693, assignable to the loss of CO from W(CO)5(E-2), and peaks at higher m/z ratios, assignable to tungsten clusters, are also observed when traces of oxygen/water were present. Using 1H and 13C NMR spectroscopy as well as 2D NMR (1H,1H COSY, 1H,1H NOESY, 13C,1H HSQC