Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• . Inert reactions were performed under an argon atmosphere. Nuclear magnetic resonance (NMR) spectra were obtained on an Agilent Premium Compact NMR spectrometer (600 MHz for 1H NMR, 150 MHz for 13C NMR) with tetramethylsilane as internal standard. Elemental analysis was performed on a Costech Elemental

Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis

• Quentin Lefebvre,
• Christophe Salomé and
• Thomas C. Fessard

Beilstein J. Org. Chem. 2020, 16, 982–988, doi:10.3762/bjoc.16.87

• coupled to benchtop analysis tools, namely thin-layer chromatography–mass spectrometry (TLC–MS, purchased from https://www.advion.com/rsc-product-note/direct-mass-analysis-of-tlc-plates/) and low-field nuclear magnetic resonance (NMR, purchased from https://www.nanalysis.com/) analysis (Scheme 1). To

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• JEOL JMS-S3000 SpiralTOF (MALDI–TOF MS). Nuclear magnetic resonance (NMR) spectra were recorded on a JEOL ECS-600 (1H 600 MHz, 13C 150 MHz) spectrometer or a JEOL ECA 600II spectrometer with UltraCoolTM probe (1H 600 MHz, 13C 150 MHz). Chemical shifts for 1H NMR are expressed in parts per million (ppm

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• Counter Solvent Dispending System (Nikko Hansen & Co., Ltd.). DMSO was distilled from CaH2 and stored over molecular sieves 4 Å. Silica gel column chromatography was performed using Wakosil® C-200 (64–210 μm). Nuclear magnetic resonance spectra were measured at 400 MHz (1H NMR) and at 100 MHz (13C NMR) in

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• gel 60, 0.040–0.063 mm) or centrifugal chromatography conducted on a Harrison Research Chromatotron model 7924T (glass plates coated with silica gel 60 PF254 containing gypsum, 2 and 4 mm thick layer) was used. Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance 400 spectrometer

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

• Cloudius R. Sagandira and
• Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

• appropriate drying agents. Nuclear magnetic resonance (NMR) spectra were recorded at room temperature as solutions in deuterated chloroform (CDCl3). A Bruker Avance-400 spectrometer (400 MHz) was used to record the spectra and the chemical shifts are reported in parts per million (ppm) with coupling constants

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

• Małgorzata Urbańczyk,
• Michał Jewgiński,
• Joanna Krzciuk-Gula,
• Jerzy Góra,
• Rafał Latajka and
• Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

• conformation of the molecule as well an on the stereochemistry of amino acid residues. The desired monoglycosylated analogues with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational nuclear magnetic resonance (NMR) studies of the designed analogues

• . We assume that ʟ-configured AFGP analogues may exhibit antifreeze activity due to their higher flexibility, hence they can expose more ice-binding groups onto the ice surface, therefore, the amphipathic character of AFGPs might play a crucial role in their activity. Experimental Nuclear magnetic

• resonance NMR spectra were recorded on a Bruker AMX600 spectrometer in deuterated dimethyl sulfoxide (DMSO-d6) at 298 K. Chemical shifts are given in ppm, relative to residual solvent signals (δH = 2.49 ppm, δC = 39.0 ppm). NMR spectral signal assignment and integration were carried out with Bruker TopSpin

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

• Emeline Benoit,
• Ahmed Fnaiche and
• Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

• indicated solvent system according to standard techniques. Proton nuclear magnetic resonance spectra were recorded on a 300 or 600 MHz spectrometer. Chemical shifts for 1H NMR spectra are recorded in parts per million from tetramethylsilane with the solvent resonance as the internal standard (chloroform, δ

Extending mechanochemical porphyrin synthesis to bulkier aromatics: tetramesitylporphyrin

• Qiwen Su and
• Tamara D. Hamilton

Beilstein J. Org. Chem. 2019, 15, 1149–1153, doi:10.3762/bjoc.15.111

• recorded on a Varian 300 MHz nuclear magnetic resonance spectrometer. Mechanochemical synthesis meso-Tetrakis[2,4,6-(trimethyl)phenyl]porphyrin. Equimolar amounts of pyrrole (0.259 g, 3.75 mmol) and 2,4,6-trimethylbenzaldehyde (0.556 g, 3.75 mmol) were placed in a 10 mL stainless steel grinding jar along

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

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• sciences. These applications include spin-labels [5][6][7], fluorophore-nitroxide probes [8], contrast agents in magnetic resonance imaging (MRI) [9], polarization transfer agents for nuclear magnetic resonance (NMR) [10][11][12][13], and radical batteries [14][15]. Furthermore, the efficient synthesis of

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

• Pedro N. Batalha,
• Luana da S. M. Forezi,
• Maria Clara R. Freitas,
• Nathalia M. de C. Tolentino,
• Ednilsom Orestes,
• José Walkimar de M. Carneiro,
• Fernanda da C. S. Boechat and
• Maria Cecília B. V. de Souza

Beilstein J. Org. Chem. 2019, 15, 388–400, doi:10.3762/bjoc.15.35

• regioselective manner, without the formation of any byproduct derived from the N-alkylation of the amide group. Structural characterization Table 1 gives the nuclear magnetic resonance spectroscopic data that allowed to confirm the structures of substances 5 and 7, and thus also confirmed the regioselectivity of

Synthesis of C₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step

• Sambasivarao Kotha and
• Saidulu Todeti

Beilstein J. Org. Chem. 2019, 15, 371–377, doi:10.3762/bjoc.15.33

• , respectively. Infrared (IR) spectra were recorded on a Nicolet Impact-400 FTIR spectrometer. Specific rotation experiments were measured at 589 nm (Na) and 25 °C (HPLC, CHCl3 stabilized with 0.7–1.0% ethanol). Proton nuclear magnetic resonance (1H NMR, 400 MHz and 500 MHz) spectra and carbon nuclear magnetic

• resonance (13C NMR, 100 MHz and 125 MHz) spectra were recorded on a Bruker spectrometer. The high-resolution mass measurements were carried out by using electrospray ionization (ESI) spectrometer. Melting points were recorded on a Veego melting point apparatus. Negishi coupling product 10 Zinc (Zn) dust was

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

• Yan Xiao,
• Bing Jing,
• Xiaoxia Liu,
• Hongyu Xue and
• Yajun Liu

Beilstein J. Org. Chem. 2019, 15, 279–284, doi:10.3762/bjoc.15.24

• reaction mixture by proton nuclear magnetic resonance spectroscopy showed that no byproduct was formed. It should be noted that the length of aliphatic dithiols had a significant effect on the reaction performance. The reaction with 1,3-propanedithiol (2b) showed the best reaction performance, providing 3a

Catalysis of linear alkene metathesis by Grubbs-type ruthenium alkylidene complexes containing hemilabile α,α-diphenyl-(monosubstituted-pyridin-2-yl)methanolato ligands

• Tegene T. Tole,
• Johan H. L. Jordaan and
• Hermanus C. M. Vosloo

Beilstein J. Org. Chem. 2019, 15, 194–209, doi:10.3762/bjoc.15.19

• and 5d Proton nuclear magnetic resonance spectrometry (1H NMR) is a powerful tool to study ruthenium alkylidene complexes and was used to study 1-octene metathesis in the presence of 1 and 2 [10][21][22]. The conversion of the benzylidene, [Ru]=CHPh, to the heptylidene, [Ru]=CHC6H13, and methylidene

Mechanistic studies of an L-proline-catalyzed pyridazine formation involving a Diels–Alder reaction with inverse electron demand

• Anne Schnell,
• J. Alexander Willms,
• S. Nozinovic and
• Marianne Engeser

Beilstein J. Org. Chem. 2019, 15, 30–43, doi:10.3762/bjoc.15.3

• from the enamine/dienophile I and the tetrazine. Thus, we decided to use NMR (nuclear magnetic resonance) spectroscopy and ESI mass spectrometry in combination with a charge-tagging strategy to get deeper insights in the presence or absence of the three intermediates by experimental means. Results 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

• ) and monosubstituted tetrahydro-7H-benzo[7]annulenone, St-Jacques' group benefited extensively from the use of dynamic nuclear magnetic resonance (DNMR) techniques [126][127]. A catalytic deuterogenation of 4,5-benzotropone (11) followed by deuteration led to deuterated 5,6,8,9-tetrahydro-7H-benzo[7

Gram-scale preparation of negative-type liquid crystals with a CF₂CF₂-carbocycle unit via an improved short-step synthetic protocol

• Tatsuya Kumon,
• Shohei Hashishita,
• Takumi Kida,
• Shigeyuki Yamada,
• Takashi Ishihara and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 148–154, doi:10.3762/bjoc.14.10

• found to be identical to the more polar adducts based on comparison of various physical data, such as the 1H, 13C, 19F nuclear magnetic resonance (NMR) signals, retardation factors (Rf values), melting points, etc. From these analyses, 3b and 3c obtained by the present protocol were eventually

An efficient synthesis of 1,6-anhydro-N-acetylmuramic acid from N-acetylglucosamine

• Matthew B. Calvert,
• Christoph Mayer and
• Alexander Titz

Beilstein J. Org. Chem. 2017, 13, 2631–2636, doi:10.3762/bjoc.13.261

• . Optical rotation was measured using a P-2000 polarimeter (Jasco, Gross-Umstadt, Germany) at 589 nm. Nuclear magnetic resonance (NMR) spectroscopy was performed on a Bruker Avance III 500 UltraShield spectrometer at 500 MHz (1H) or 126 MHz (13C) or a Bruker Fourier 300 spectrometer at 300 MHz (1H) or 75

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones

• Sergii V. Melnykov,
• Andrii S. Pataman,
• Yurii V. Dmytriv,
• Svitlana V. Shishkina,
• Mykhailo V. Vovk and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2017, 13, 2617–2625, doi:10.3762/bjoc.13.259

• Organofluorine compounds now play an essential role in the development of new materials for solar cells [1][2][3], radiotracers for PET imaging [4], agrochemicals [5][6], sensitive chemical probes for 19F nuclear magnetic resonance investigation of biological experiments [7][8], and are most widely used in the

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

• Markéta Bláhová,
• Sergey K. Filippov,
• Lubomír Kováčik,
• Jiří Horský,
• Simona Hybelbauerová,
• Zdenka Syrová,
• Tomáš Křížek and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

• were studied by a set of methods allowing characterization of supramolecular behavior at various levels – from binary complexation, over supramolecular oligomers to large assemblies; namely by isothermal titration calorimetry (ITC) [16], 1H nuclear magnetic resonance spectroscopy (1H NMR), dynamic

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• . The standard deviations of experimentally derived CE50% of complexes were below 3% (for majority of experimental points about 1%) for various experimental parameters such as ion-spray voltage (−3.5 kV and −4.5 kV) and MRM scanning time. Nuclear magnetic resonance (NMR) The 1H NMR spectra were recorded

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

• Patrick A. Julien,
• Ivani Malvestiti and
• Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

• analysis of the crude reaction product by 1H nuclear magnetic resonance (NMR) spectroscopy (see Supporting Information File 1) suggested quantitative conversion, with the presence of only trace impurities. Importantly, as the melting points of the starting materials and the product are considerably above

Conformational impact of structural modifications in 2-fluorocyclohexanone

• Francisco A. Martins,
• Josué M. Silla and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2017, 13, 1781–1787, doi:10.3762/bjoc.13.172

• population of the equatorial conformer increased with the solvent polarity, as dipolar repulsion between Y and F decreases in solvents with increasing dielectric constants. Nuclear magnetic resonance (NMR) parameters, namely chemical shifts and coupling constants, can be useful to provide information on

An efficient Pd–NHC catalyst system in situ generated from Na₂PdCl₄ and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

• Nan Sun,
• Meng Chen,
• Liqun Jin,
• Wei Zhao,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

• grade and used as purchased. Monomethylated PEG1900 (MeO-PEG1900-OH) was obtained from Meryer Chem. Tech. Co. Ltd, China. All proton and 13C nuclear magnetic resonance (NMR) spectra were recorded on Bruker AVANCE III 500 MHz spectrometer in deuterated solvents with tetramethylsilane (TMS) as internal