Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• and 100 MHz for 1H and 13C, respectively). 1H NMR and 13C NMR spectra were referenced to residual solvent peaks. High-resolution mass spectrometry (HRMS) analyses were carried out on a Dual-ESI Q-TOF 6520 (Agilent Technologies) mass spectrometer. Photophysical properties were analyzed in 10−5 M

Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions

• Robin Schulte and
• Heiko Ihmels

Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41

• the neighboring methyl group at the reaction center. The novel compounds 2a, 2b, and 3 were identified and characterized by NMR spectroscopy (1H, 13C, COSY, HSQC, HMBC), melting point, and elemental analysis. In addition, the structure of product 2b was supported by high resolution mass spectrometry

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• Abstract Four new phenolic siderophores were isolated from the actinomycete Nocardia altamirensis along with the known natural product amamistatin B and a putative biosynthetic shunt product. The structures of all compounds were elucidated through 1D and 2D NMR analyses as well as mass spectrometry. The

• conditions. The structures of these natural products were verified by high-resolution mass spectrometry, tandem mass spectrometry as well as 1D and 2D NMR analyses. Their absolute configuration is consistent with the already known amamistatin B according to a comparison of optical rotation values and NOE

Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

• Yuki Naito,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

• column (Mightysil RP-18 GP II 250-4.6 (5 µm), Cica) using a mixture of H2O/MeCN/H3PO4 (60/40/0.1%) as a mobile phase. All chromatograms were recorded using an LC workstation (LabSolutions DB, Shimadzu). Helium gas was used as a carrier gas for the gas chromatography/mass spectrometry (GC–MS) analyses. 1H

Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines

• Marco Manenti,
• Leonardo Lo Presti,
• Giorgio Molteni and
• Alessandra Silvani

Beilstein J. Org. Chem. 2022, 18, 303–308, doi:10.3762/bjoc.18.34

• optimized conditions (Table 1, entry 12) followed by flash chromatography, the unprecedented bisoxindole 2a was fully characterized by high-resolution mass spectrometry and by one- and two-dimensional NMR analysis. In particular, from HSQC, HMBC and COSY experiments all single frequencies could be safely

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• , but their efficiencies were found to be lower than that of 1,10-phenanthroline. Metal impurities in FeCl3·6H2O were detected by using ICP mass spectrometry. Lipshutz and co-workers prepared nanoparticles from inexpensive iron(III) chloride containing reusable palladium in ppm level and XPhoS as ligand

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• kindly provided by Prof. Sabine Flitsch, University of Manchester. We thank Dr. Reynard Spiess for providing the HRMS data through the Michael Barber Centre for Collaborative Mass Spectrometry. Funding This work was supported by the Flexible Talent Mobility Account (grant BB/S507957/1), funded by the

Diametric calix[6]arene-based phosphine gold(I) cavitands

• Gabriele Giovanardi,
• Andrea Secchi,
• Arturo Arduini and
• Gianpiero Cera

Beilstein J. Org. Chem. 2022, 18, 190–196, doi:10.3762/bjoc.18.21

• via conventional protocols using (Me2S)AuCl. Notably, the organometallic macrocycles A,B,C(AuCl)2 could be isolated via column chromatography separation. Gold(I) catalysts were subsequently fully characterized by NMR analysis and high-resolution mass spectrometry. The conformation of the catalysts, in

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

• nucleoside under basic conditions of 2 M NaOH in dioxane and water (1:1) was the first of its kind in the literature. The progress of the reaction (from nucleoside 22b to nucleoside 9b) was investigated by mass spectrometry (MS) and a sample of the reaction mixture was collected during the reaction. The mass

• -homoarabinofuranosyl nucleosides 9a,b. Chemical synthesis of nucleosides 9a,b starting from diacetone ᴅ-glucofuranose. a) Plausible mechanism for the synthesis of (5′R)-3′-azido-3′-deoxy-2′-O,5′-C-bridged-β-ᴅ-homoarabinofuranosyl nucleosides 9a,b from 16a,b and b) intermediates detected on the basis of mass

• spectrometry during the conversion of 22b into 9b. Supporting Information Supporting Information File 2: Experimental part and NMR spectra. Funding We are grateful to the Institute of Imminence, University of Delhi for providing financial support to strengthen research and development. We are thankful to the

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• phenethylamine derivatives (amphetamine, methamphetamine, 2,5-dimethoxy-4-methylamphetamine, mescaline, ephedrine, and norephedrine). The reaction products were separated by thin-layer chromatography and analyzed by elemental analysis, nuclear magnetic resonance, infrared spectroscopy, and mass spectrometry. In

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

• Tanmoy Halder and
• Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

• , DEPT-135, 13C NMR, COSY, and HSQC as well as mass spectrometry using HRMS. The NMR data were found to correlate well with the data reported for the natural polysaccharide [38]. Conclusion In conclusion, the trisaccharide repeating unit of the O-polysaccharide of Providencia stuartii O49 in its p

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• DICzTRZ were determined by a combination of NMR spectroscopy, mass spectrometry, and IR spectroscopy. Theoretical calculations Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations in the gas phase at the PBE0/6-31G(d,p) level reveal the potential of DICzTRZ as a TADF material. The

Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

• Nicolai Wippert,
• Martin Nieger,
• Claudine Herlan,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187

• , failed under similar procedures. Abbreviations TFA, trifluoroacetic acid; DMSO, dimethyl sulfoxide; THF, tetrahydrofuran, TLC, thin-layer chromatography, LC–MS, liquid chromatography/mass spectrometry. Structural differences of several known (2–4) and so far unknown (5 and 6) pyrazolo[3,4-d][1,2,3]-3H

GlycoBioinformatics

• Kiyoko F. Aoki-Kinoshita,
• Frédérique Lisacek,
• Niclas Karlsson,
• Daniel Kolarich and
• Nicolle H. Packer

Beilstein J. Org. Chem. 2021, 17, 2726–2728, doi:10.3762/bjoc.17.184

• knowledge. Most structural data at this stage is generated by analytical approaches, such as mass spectrometry (MS), high-pressure liquid chromatography (HPLC), and capillary electrophoresis (CE). The articles by Phung et al. [9] and by Lippold et al. [10] suggest ways of combining and customising available

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• ). Multiplicity is defined as s = singlet, d = doublet, t = triplet, q = quartet, p = pentet, m = multiplet. NMR spectra were analyzed with NMR software MestReNova, version 14.2.0-26256 (Mestrelab Research S.L.). High-resolution mass spectra were performed by the LMU Mass Spectrometry Service applying a Thermo

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• . Analysis of data combination from ovicidal activity, mass spectrometry, and metabolomics using HPLC-diode array detector-MS (HPLC-DAD-MS), partial least squares regression analysis (PLS-DA), and a correlation map (univariate correlation analyses) enabled the prediction of compounds that have a positive

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A–C (1–3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR

• Wang of the Marine Biodiscovery Centre, Aberdeen for assisting in NMR, mass spectrometry and Marfey analyses, respectively. We also appreciate the support of Dr. Soji Fakoya and Blessing Akinboyo of Ondo State University of Science and Technology, Okitipupa, Nigeria, for their support in the collection

Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

• Matthew J. Fleming and
• David M. Hodgson

Beilstein J. Org. Chem. 2021, 17, 2385–2389, doi:10.3762/bjoc.17.155

• . Supporting Information Supporting Information File 268: Experimental procedures and characterisation data for all new compounds. Acknowledgements We thank the EPSRC National Mass Spectrometry Service Centre for mass spectra. Funding The EPSRC and GlaxoSmithKline are acknowledged for a CASE studentship to M

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

• Pieterjan Winant and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 2315–2320, doi:10.3762/bjoc.17.149

• . Funding We thank the KU Leuven (Project C14/19/78) and the FWO-Vlaanderen (bilateral project G0F6619N) for financial support. Mass spectrometry was made possible by the support of the Hercules Foundation of the Flemish Government (grant 20100225-7).

Facile and innovative catalytic protocol for intramolecular Friedel–Crafts cyclization of Morita–Baylis–Hillman adducts: Synergistic combination of chiral (salen)chromium(III)/BF₃·OEt₂ catalysis

• Karthikeyan Soundararajan,
• Helen Ratna Monica Jeyarajan,
• Raju Subimol Kamarajapurathu and
• Karthik Krishna Kumar Ayyanoth

Beilstein J. Org. Chem. 2021, 17, 2186–2193, doi:10.3762/bjoc.17.140

• (6a–f) were deduced from 1H NMR, 13C NMR, elemental analysis and high-resolution mass spectrometry. To account for the observed synthesis of indene from MBH adducts a model was suggested based on the reports of Rawal et al. [17][19], Katsuki et al. [20][21] and Jurczak et al. [22]. The proposed model

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• behaves as a terminal oxidant to form α-aminoalkyl radicals, whereas the formation of an Fe-peroxo species in the catalytic cycle was confirmed using a combination of EPR and ESI mass spectrometry experiments (Scheme 31D). One-pot processes for the synthesis of benzo[b]furans from aryl- or alkylketones

Development of N-F fluorinating agents and their fluorinations: Historical perspective

• Teruo Umemoto,
• Yuhao Yang and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• /glycoproteomics-based mass spectrometry, would further support the proposed TF–glycogene relationships [43]. Some caveats in our analysis are important to note. First, we only used selected values of RP and ρ to filter TF–glycogene relationships from the Cistrome Cancer DB. Further studies are needed in order to

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• the presence of 10 mM MgCl2. Enzyme products were extracted from the assays with hexane and analyzed using gas chromatography–mass spectrometry. Myrcene (9); (E)-β-ocimene (10); (Z)-β-ocimene (11); linalool (5); (E,E)-α-farnesene (12); (E)-β-caryophyllene (1); (E,E)-β-springene (13); (E,E,E)-α

Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

• Feng Xiong,
• Bo Li,
• Chenrui Yang,
• Liang Zou,
• Wenbo Ma,
• Linghui Gu,
• Ruhuai Mei and
• Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

• determined by 1H NMR spectroscopy. Chromatographic separation was carried out on silica gel 60H (200–300 mesh) manufactured by Qingdao Haiyang Chemical Group Co. (China). High-resolution mass spectrometry (HRMS) was measured on a Thermo-DFS mass spectrometer. NMR spectra were recorded on a JEOL 600 NMR