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

• -heterotetracenes and -hexacene were clearly identified, fully characterized, and their structures confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS) via matrix-assisted laser desorption/ionization (MALDI) (Supporting Information File 1, Figures S1–S5). In the 1H NMR spectra, the

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• fully characterized by 1H and 13C NMR spectroscopy and mass spectrometry (see Supporting Information File 1) and the data were found to be consistent with the proposed structures. For the hexakis-propargyl ether TBTQ-(OP)6, the signals at δ = 2.53 ppm in the 1H NMR spectrum and at δ = 78.98 and 76.07

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• to the trimethylsumanene synthesis, Sakurai and his co-workers selectively generated mono-, di- and trianions (29–31) using t-BuLi as a base and the formation of these sequential anions were confirmed by 1H and 13C NMR spectroscopy (Scheme 4) [32]. Next, the in situ generated trianion 31 was quenched

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Valerii V. Tkachev,
• Andrey N. Utenyshev,
• Olga Yu. Karlutova,
• Alexander D. Dubonosov,
• Vladimir A. Bren,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2020, 16, 1820–1829, doi:10.3762/bjoc.16.149

• -isomers and of products of the photoinduced rearrangement completed by 1,5-H shift reaction, 3a,4-dihydronaphtho[2,3-c]furans(pyrroles) C, were established based on the data of 1H and 13C NMR spectroscopy and X-ray diffraction studies. Keywords: benzo[b]thiophene; fulgide; fulgimide; photorearrangement

• afford exclusively fulgimides 3Z and 7E, respectively, as the single products (Scheme 2 and Scheme 3). According to IR, 1H and 13C NMR spectroscopy data Z- and E-isomers of fulgide 3 exist in the form of the open isomers O. This was also confirmed by X-ray diffraction study. The molecular structures of

• -, Z-isomers and closed forms C were identified with the use of 1H and 13C NMR spectroscopy and their molecular structures confirmed by X-ray diffraction studies. Experimental General: The 1H and 13C NMR spectra in CDCl3 were obtained on an integrated analytical LC-SPE-NMR-MS AVANCE-600 system from

Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner–Wadsworth–Emmons-based approach

• Rhys A. Lippa,
• John A. Murphy and
• Tim N. Barrett

Beilstein J. Org. Chem. 2020, 16, 1617–1626, doi:10.3762/bjoc.16.134

• with CD3OD by 1H and 13C NMR spectroscopy indicated the formation of the monolabelled compound 17 as the major product, demonstrating that lithiation only occurs at a single position of compound 13 (Scheme 6). When performed on a multigram scale, phosphonate 7 was isolated in 68% yield after

Aryl-substituted acridanes as hosts for TADF-based OLEDs

• Naveen Masimukku,
• Dalius Gudeika,
• Oleksandr Bezvikonnyi,
• Ihor Syvorotka,
• Rasa Keruckiene,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

• presence of a palladium catalyst, with yields ranging from 27 to 50%. The chemical structures of 3–6 were confirmed by 1H and 13C NMR spectroscopy, elemental analysis and mass spectrometry. Transparent thin films of these compounds could be prepared by vacuum evaporation or by spin coating from solutions

Direct borylation of terrylene and quaterrylene

• Haruka Kano,
• Keiji Uehara,
• Kyohei Matsuo,
• Hironobu Hayashi,
• Hiroko Yamada and
• Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

• 2,5,10,13-tetramesitylterrylene (TM4) in 58% yield. TM4 was successfully isolated through a silica gel pad and by reprecipitation. The structure of TM4 was characterized by mass spectrometry and 1H and 13C NMR spectroscopy. High-resolution MALDI mass spectrometry detected the parent ion peak at m/z

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• 13C NMR spectroscopy, and HRMS. Furthermore, the structures of compounds I18 and III4 were verified by X-ray diffractometry (Figure 3). Crystallographic data for crystalline I18 and III4 have been deposited with the Cambridge Crystallographic Data Centre (CCDC 1959130, CCDC 1959152). HPPD inhibition The

• that yielded compound F. Subsequent preparations for compounds G, H, J and II were respectively the same as for compounds C, D, E and I. All intermediates were synthesized and characterized as detailed in Supporting Information File 1. The structures of all prepared compounds were confirmed by 1H and

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

• Renata Kaczmarek,
• Dariusz Korczyński,
• James R. Green and
• Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

• of alkynyl nucleosides 2 and 3 were confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry [64][65]. The conversion of alkynyl nucleosides 2 and 3 into the corresponding dicobalt hexacarbonyl nucleosides complexes of 4 and 5 was accomplished at room temperature (Co2(CO)8, THF

Preparation of anthracene-based tetraperimidine hexafluorophosphate and selective recognition of chromium(III) ions

• Qing-Xiang Liu,
• Feng Yang,
• Zhi-Xiang Zhao,
• Shao-Cong Yu and
• Yue Ding

Beilstein J. Org. Chem. 2019, 15, 2847–2855, doi:10.3762/bjoc.15.278

• 10.3762/bjoc.15.278 Abstract A novel anthracene-based tetraperimidine hexafluorophosphate 3 was prepared, and its structure was determined through X-ray analysis, HRMS as well as 1H and 13C NMR spectroscopy. In the cationic moiety of 3, two (N-ethylperimidinyl–C2H4)2NCH2– arms were attached to the 9- and

• X-ray analysis as well as 1H and 13C NMR spectroscopy. Particularly, compound 3 was tested as a chemosensor for the recognition of Cr3+ through fluorescence, UV, IR, and 1H NMR spectroscopy along with HRMS. Altogether, the results indicate the utility of 3 as an effective chemosensor for Cr3

• upon complexation, and the C=N absorption band at 1664 cm−1 shifted to a value of 1672 cm−1. Conclusion In summary, a new anthracene-based tetraperimidine hexafluorophosphate 3 was prepared, and its structure was determined through X-ray analysis and 1H and 13C NMR spectroscopy. Compound 3 was proved

Photochromic diarylethene ligands featuring 2-(imidazol-2-yl)pyridine coordination site and their iron(II) complexes

• Andrey G. Lvov,
• Max Mörtel,
• Anton V. Yadykov,
• Frank W. Heinemann,
• Valerii Z. Shirinian and
• Marat M. Khusniyarov

Beilstein J. Org. Chem. 2019, 15, 2428–2437, doi:10.3762/bjoc.15.235

• successfully applied for the synthesis of a new family of photochromic ligands. The structures of the synthesized diarylethene-based ligands 3, 4, 6, and 7 were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry. The molecular structure of 6 was additionally confirmed by X-ray crystallography. In

Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs₂CO₃-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

• Mio Matsumura,
• Yuki Kitamura,
• Arisa Yamauchi,
• Yoshitaka Kanazawa,
• Yuki Murata,
• Tadashi Hyodo,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2019, 15, 2029–2035, doi:10.3762/bjoc.15.199

• was fully characterized by 1H and 13C NMR spectroscopy and HRMS, and further confirmed by single-crystal X-ray diffraction (XRD) analysis. The ORTEP drawing and packing structure of 2a obtained from the single crystal XRD analysis are illustrated in Figure 1. The crystal structure contained two

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

• good yields (Scheme 5, Table 3). The structures of the 1,5-diacyl-5-hydroxypyrazolines 5 were unambiguously assigned by 1H and 13C NMR spectroscopy, in selected cases by NOESY, HSQC, and HMBC experiments, as well as by EI mass spectrometry and the elemental composition was confirmed by combustion

Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

• Sven Götz,
• Andreas Schneider and
• Arne Lützen

Beilstein J. Org. Chem. 2019, 15, 1339–1346, doi:10.3762/bjoc.15.133

• these studies an intermediate saddle conformer could also be isolated and characterized by 1H and 13C NMR spectroscopy. The HPLC separation method was further developed in order to allow investigations on the racemization behavior of the cyclotriveratrylene derivative. Keywords: chiral resolution

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• final compounds were carefully characterized by 1H and 13C NMR spectroscopy and electrospray ionization mass spectroscopy (ESI-MS, Supporting Information File 1, Figures S1–S8). UV–vis absorption and fluorescence spectra of 1 in different solvents, including CHCl3, MeCN, MeOH, H2O, and mixed solvent

Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands

• Jennifer Klose,
• Tobias Severin,
• Peter Hahn,
• Alexander Jeremies,
• Jens Bergmann,
• Daniel Fuhrmann,
• Jan Griebel,
• Bernd Abel and
• Berthold Kersting

Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81

• salts are stable in air both in solution and in the solid state, and are very soluble in a range of common polar organic solvents (CH3CN, EtOH, MeOH). The new compounds gave satisfactory elemental analyses and were characterized by mass spectrometry, spectroscopic methods (IR, UV–vis, 1H and 13C NMR

• spectroscopy) and in case of 3' and 5–8 also by X-ray crystal structure analysis. Characterization of complexes IR and NMR spectroscopy Table 1 lists selected analytical data for the synthesized compounds. The infrared spectra of 1–9 were recorded in the 4000–400 cm−1 spectral range. The IR spectra display in

Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes

• Krzysztof M. Zwoliński and
• Julita Eilmes

Beilstein J. Org. Chem. 2019, 15, 617–622, doi:10.3762/bjoc.15.57

• -ATR, 1H and 13C NMR spectroscopy and elemental analysis. Keywords: crown ether; dibenzotetraaza[14]annulene; DBTAA; macrocycle; Schiff base; Introduction The design and synthesis of novel polycyclic receptor architecture is of fundamental importance, since model recognition studies contribute to

• been fully characterized by FTIR-ATR, 1H and 13C NMR spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESIMS) and elemental analysis, and the results are in agreement with expected structures (vide infra). Both the crown ether-capped compounds 3a and 3b are highly symmetrical

• satisfactory 26–28% isolated yields and fully characterized based on HR-ESIMS, FTIR-ATR, 1H and 13C NMR spectroscopy and elemental analysis. These novel receptors are expected to bind both the transition, alkali and alkaline-earth metals, and also, after DBTAA subunit metalation the whole ion pairs. The

Microwave-assisted synthesis of biologically relevant steroidal 17-exo-pyrazol-5'-ones from a norpregnene precursor by a side-chain elongation/heterocyclization sequence

• Gergő Mótyán,
• László Mérai,
• Márton Attila Kiss,
• Zsuzsanna Schelz,
• Izabella Sinka,
• István Zupkó and
• Éva Frank

Beilstein J. Org. Chem. 2018, 14, 2589–2596, doi:10.3762/bjoc.14.236

• heterocyclization. In order to enlarge the compound library available for pharmacological studies, the 3β-OH analogs 7a–j of the primary products 6a–j were also synthesized through simple alkaline deacetylation (Scheme 2, Table 1). The structures of all synthesized compounds were characterized by 1H and 13C NMR

• spectroscopy supplemented by IR and MS measurements. The dependence of the tautomeric equilibrium on the polarity of the applied solvent was observed during the NMR experiments. For example, in the 1H NMR spectrum of compound 7f recorded immediately after dissolution in CDCl3, the pyrazolone heterocyclic ring

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

• Jiang Liu,
• Peter Leonard,
• Sebastian L. Müller,
• Constantin Daniliuc and
• Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

• by ESI–TOF mass spectra, 1H and 13C NMR spectroscopy as well as 2D NMR spectra (Supporting Information File 1). The NMR data gave evidence of the structural assignment of the 5’-azido compounds and the macrocycles. A strong upfield shift (≈10 ppm) for the C5’-carbon signal as well as a moderate

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• established by 1H and 13C NMR spectroscopy as well as by IR spectroscopy and MALDI–TOF mass spectrometry. Their compositions were determined by elementary analysis. A standard set of signals typical for distal disubstituted calixarenes was found in the 1H NMR spectra of 4a and b (Supporting Information File 1

Efficient catenane synthesis by cucurbit[6]uril-mediated azide–alkyne cycloaddition

• Antony Wing Hung Ng,
• Chi-Chung Yee,
• Kai Wang and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2018, 14, 1846–1853, doi:10.3762/bjoc.14.158

• complex helps the CBAAC by avoiding any cycloadditions outside of the CB[6] cavity and that CBAAC can be an efficient strategy for catenane synthesis. Cat-1 and its interlocked nature were further characterized by MS2, 1H and 13C NMR spectroscopy. The PF6− salt of Cat-1 was isolated in 69% yield as a

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

• . Consequently it was not removed prior to the rearrangement experiments. Treatment of 11i and 11k with the mild base piperidine led to the formation of α,β-unsaturated sulfinylimines 12i and 12k. The structures of the rearranged products were proven unequivocally by 1H and 13C NMR spectroscopy and X-ray crystal

Is the tungsten(IV) complex (NEt₄)₂[WO(mnt)₂] a functional analogue of acetylene hydratase?

• Matthias Schreyer and
• Lukas Hintermann

Beilstein J. Org. Chem. 2017, 13, 2332–2339, doi:10.3762/bjoc.13.230

• through the solution for 4 h at 35 °C produced plenty of precipitate in the DNPH-exhaust solution, which was shown to be acetaldehyde dinitrophenylhydrazone 9 by 1H and 13C NMR spectroscopy. The NMR spectrum of the catalyst solution contained distinct signals for acetaldehyde (δH 2.11, 9.64; 3J(H,H) = 9.6

• 13C NMR spectroscopy, IR spectroscopy, and by its dark purple color. A diagnostic analytical property in solution is δC of C-2/3 in the mnt ligand (δC = 140.4 ppm for 1) that depends on changes in the oxidation state, particularly oxidation to [WO2(mnt)2]2− (δC = 123.3 ppm). In a preliminary

• -Markovnikov hydration [18][24][25][26][27][28]. Results and Discussion Tungsten complex (NEt4)2[WO(mnt)2] (1) was prepared according to the literature procedure from Na2WO4, Na2mnt and buffered aqueous dithionite, followed by precipitation with Et4NBr (Scheme 3a) [29]. The compound was characterized by 1H and

Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

• Henryk Myszka,
• Patrycja Sokołowska,
• Agnieszka Cieślińska,
• Andrzej Nowacki,
• Maciej Jaśkiewicz,
• Wojciech Kamysz and
• Beata Liberek

Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227

• NaBH3CN resulted in N-ethylamino (11) and N,N-diethylamino (12) saponins, which were separated by column chromatography. An analogous reaction of 4 with 3 molar excess of propionaldehyde, followed by the reduction with NaBH3CN resulted solely in N,N-dipropylaminosaponin 13. The 1H and 13C NMR spectroscopy

18-Hydroxydolabella-3,7-diene synthase – a diterpene synthase from Chitinophaga pinensis

• Jeroen S. Dickschat,
• Jan Rinkel,
• Patrick Rabe,
• Arman Beyraghdar Kashkooli and
• Harro J. Bouwmeester

Beilstein J. Org. Chem. 2017, 13, 1770–1780, doi:10.3762/bjoc.13.171

• expressing HdS-mit yielded 26.2 mg of the pure diterpene alcohol from 100 g of fresh leaves (0.03% of fresh leaf weight). The obtained material was identical to 3 obtained by in vitro incubation of GGPP with recombinant HdS by 1H and 13C NMR spectroscopy. A compound with the same structure as determined from