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Search for "neat" in Full Text gives 321 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

  • Aaron H. Shoemaker,
  • Elizabeth A. Foker,
  • Elena P. Uttaro,
  • Sarah K. Beitel and
  • Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

Graphical Abstract
  • substrates. a) Substrate 7, reagents and conditions: 1) neat (5 equiv 5), 24 h; 2) Boc2O, NaHCO3, EtOH, ultrasound, 1 h, 88% (2 steps); 3) AcOH, hν (360 nm), 6 h, 74%. b) Substrate 9, reagents and conditions: 1) 11 (2 equiv), EtOAc, 23 °C, 1 h; 2) Boc2O, NaHCO3, EtOH, ultrasound, 23 °C, 1 h, 68% (2 steps); 3
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Published 23 Oct 2023

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

  • Bel Youssouf G. Mountessou,
  • Élodie Gisèle M. Anoumedem,
  • Blondelle M. Kemkuignou,
  • Yasmina Marin-Felix,
  • Frank Surup,
  • Marc Stadler and
  • Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

Graphical Abstract
  • , white neat solid, tR = 85 min). The LC–MS analysis of other fractions suggested the presence of very low amounts of compounds and these fractions were not further investigated. Series C (1.2 g) eluted with CH2Cl2/MeOH 97.5:2.5 (v/v) was divided into three portions of 400 mg each. Every portion was
  • oil, tR = 8 min), 9 (1.3 mg, yellow oil, tR = 14 min), 3 (2.76 mg, white neat solid, tR = 16 min), and 1 (0.79 mg, yellow oil, tR = 22 min), respectively. Series E (294 mg) was further purified to yield compounds 5 (0.95 mg, white amorphous powder, tR = 35.20 min), 17 (6.1 mg, white amorphous powder
  • , tR = 11.21 min), and 7 (1.45 mg, yellow neat solid, tR = 15.00 min), 4 (2.45 mg, white amorphous powder, tR = 22.00 min), respectively. Successive purifications of series F (898 mg) over normal (CH2CH2/MeOH 92:8, Nucleosil 120 OH Diol column) and reversed-phase preparative HLPC (Gilson, PLC 2020
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Published 13 Oct 2023

Cyclization of 1-aryl-4,4,4-trichlorobut-2-en-1-ones into 3-trichloromethylindan-1-ones in triflic acid

  • Vladislav A. Sokolov,
  • Andrei A. Golushko,
  • Irina A. Boyarskaya and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2023, 19, 1460–1470, doi:10.3762/bjoc.19.105

Graphical Abstract
  • was found that enones 2 were transformed into the corresponding 3-trichloromethylindan-1-ones 3 upon heating in neat TfOH at 80 °C for 2–10 h (Scheme 5). Under the same reaction conditions, hydroxy ketones 1 were cyclized into indanones 3 as well (Scheme 6). The structure of compound 3a was confirmed
  • Brønsted and Lewis acids were also tested for this cyclization. Thus, enones 2a and 2e were not transformed into the corresponding indanones 3 in neat sulfuric acid (H2SO4) at room temperature for 3 days. That is in accord with literature data [19], where H2SO4 was used for dehydration of hydroxy ketones 1
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Published 27 Sep 2023

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

  • Dileep Kumar Singh and
  • Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

Graphical Abstract
  • of the catalyst for up to nine consecutive runs without loss of catalytic activity. Recently, Rohit et al. [86] described a modified Clauson–Kaas synthesis of N-substituted pyrrole with up to 89% yields by microwave irradiation at 120 °C in neat conditions by reacting amines 66 with 2,5-DMTHF (2) in
  • derivatives 77 in good to excellent yields using a microwave-assisted and bismuth nitrate Bi(NO3)3∙5H2O-catalyzed reaction between various amines 76 and 2,5-dimethoxytetrahydrofuran (2) in neat, H2O or THF (Scheme 37). This approach provides different pyrrole derivatives without the use of sensitive or
  • , H2O, neat), reaction times (10–22 minutes), and amount of oxone were investigated in order to stabilize the best reaction conditions. Among these, CH3CN as the best solvent system, 0.09 g of oxone, and a temperature of 110 ± 10 °C were chosen as optimized reaction conditions and used for the synthesis
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Published 27 Jun 2023

A fluorescent probe for detection of Hg2+ ions constructed by tetramethyl cucurbit[6]uril and 1,2-bis(4-pyridyl)ethene

  • Xiaoqian Chen,
  • Naqin Yang,
  • Yue Ma,
  • Xinan Yang and
  • Peihua Ma

Beilstein J. Org. Chem. 2023, 19, 864–872, doi:10.3762/bjoc.19.63

Graphical Abstract
  • 6.5) of probe G@TMeQ[6] (3.0 × 10−5 mol·L−1) to Hg2+ ions; (b) detection limit of probe G@TMeQ[6] to Hg2+ ions. (A) Titration 1H NMR spectra (400 MHz) obtained for TMeQ[6] with (a) 0.00, (b) 0.50, (c) 1.00 and (d) 1.20 equiv of G and (e) neat TMeQ[6] (5.0 × 10−4 mol·L−1); (B) titration 1H NMR spectra
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Published 13 Jun 2023

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

  • Lukáš Marek,
  • Jiří Váňa,
  • Jan Svoboda and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

Graphical Abstract
  • . Elemental analyses were performed on a Flash 2000 Organic Elemental Analyser (Thermofisher). For samples containing chlorine, mercurimetric titration was used. IR spectra were recorded on a Nicolet iS50 equipped with an ATR diamond crystal (neat solid samples). Flash chromatography was performed using a
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Published 09 Jun 2023

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

  • Sarot Cheenpracha,
  • Ratchanaporn Chokchaisiri,
  • Lucksagoon Ganranoo,
  • Sareeya Bureekaew,
  • Thunwadee Limtharakul and
  • Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

Graphical Abstract
  • silica gel CC eluting with 100% CH2Cl2 afforded compound 2 (6.9 mg). 14β-Hydroxycassa-11(12),13(15)-dien-12,16-olide (1): amorphous, white powder; −22 (c 0.01, MeOH); UV (MeOH) λmax (log ε) 283 (4.20) nm; ECD (0.001, MeOH) λmax (Δε) 241 (+11.5), 271 (−10.4), 297 (+2.5) nm; IR (neat) νmax 3429, 2926
  • ) 243 (+21.1), 330 (−4.70) nm; IR (neat) νmax: 2973, 1724, 1660, 1508, 1733 cm−1; 1H NMR (500 MHz, CDCl3) and 13C NMR (125 MHz, CDCl3) spectra, see Table 1; HRESI–TOF–MS m/z: 733.4305 [M + H]+ (calcd for C44H61O9, 733.4310). α-Glucosidase inhibitory assay α-Glucosidase inhibitory activity was performed
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Published 11 May 2023

An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

  • Shubham Sharma,
  • Dharmender Singh,
  • Sunit Kumar,
  • Vaishali,
  • Rahul Jamra,
  • Naveen Banyal,
  • Deepika,
  • Chandi C. Malakar and
  • Virender Singh

Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22

Graphical Abstract
  • thioamidation reaction. After that, DMSO and NMP were also screened as solvents in the absence of base, but a longer reaction time was required for similar transformation (7 h) (entries 20 and 21, Table 1). A reaction of model substrates under neat conditions delivered product 1C in poor yield (entry 22, Table
  • yield was observed (entries 2–5, Table 2). The oxidant TBHP (10 equiv) failed to deliver the anticipated product in good yield (36%, entry 6, Table 2). Similar results were obtained with H2O2 (25.0 equiv) under neat reaction conditions (entry 7, Table 2). Next, we performed the oxidative amidation
  • , 0.25 mm). Column chromatography was performed using Spectrochem silica gel (60–120 mesh). Melting points were determined in open capillary tubes on the Precision Digital melting point apparatus (LABCO make) containing silicone oil, and the results are uncorrected. IR spectra (neat) were recorded on an
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Published 02 Mar 2023

Germacrene B – a central intermediate in sesquiterpene biosynthesis

  • Houchao Xu and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

Graphical Abstract
  •  11), is only known as a synthetic compound. This hydrocarbon has first been obtained by dehydration of (+)-valerianol (42) with SOCl2 or POCl3, yielding – besides the Hofmann product as main product (75%) – (+)-39 (25%, [α]D20 = +167.5, neat) (Scheme 12B) [95]. After the first description of 39, also
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Published 20 Feb 2023

Inline purification in continuous flow synthesis – opportunities and challenges

  • Jorge García-Lacuna and
  • Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

Graphical Abstract
  • system consists of a membrane reactor for the enzyme-mediated synthesis, a saturator vessel for the continuous supply of the amine donor, and a crystallizer where the desired product precipitates. Flow reactions can be performed as neat reactions in certain circumstances allowing for the precipitation of
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Published 16 Dec 2022

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

  • Merve Karaman,
  • Abhishek Kumar Gupta,
  • Subeesh Madayanad Suresh,
  • Tomas Matulaitis,
  • Lorenzo Mardegan,
  • Daniel Tordera,
  • Henk J. Bolink,
  • Sen Wu,
  • Stuart Warriner,
  • Ifor D. Samuel and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

Graphical Abstract
  • TADF emitter, imCzDPS (λPL = 440 nm, ΦPL = 44%, neat film) [19]. The EL of the LEEC was red-shifted at λEL of 470 nm compared to the PL. Following these initial reports Edman and co-workers demonstrated how neutral TADF small molecules [20], polymers [21], and dendrimers [22] could be employed in LEECs
  • tert-butylcarbazole as donor groups [24]. Pym-CZ showed red emission in dichloromethane (λPL = 691 nm, ΦPL = 43%) and in the neat film (λPL = 583 nm, ΦPL = 15%). The emission is further red-shifted and attenuated in Pym-tBuCZ in dichloromethane (λPL = 740 nm, ΦPL = 8%) and in the neat film (λPL = 593
  • DiKTa (λPL = 466 nm, FWHM = 40 nm, ΦPL = 70%, ΔEST = 0.20 eV, τD = 168 μs, 2 wt % mCP) in the same host [28]. Both emitters exhibited high ΦPL values in the mCP film at 71% and 61% under nitrogen, and these reduced to 57% and 53% in air for DiKTa-OBuIm and DiKTa-DPA-OBuIm, respectively. As neat thin
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Published 22 Sep 2022

Polymer and small molecule mechanochemistry: closer than ever

  • José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1225–1235, doi:10.3762/bjoc.18.128

Graphical Abstract
  • the covalent capsule 5 (made from resorcinarene caps connected by four dihydrazone units of ʟ-cysteine) with C60 and C70 fullerenes upon neat ball milling in a planetary ball mill (Figure 6). The mechanochemical complexation is remarkable since the porous capsule does not possess large enough openings
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Published 14 Sep 2022

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

  • Ashish Kumar Mazumdar,
  • Gyana Prakash Nanda,
  • Nisha Yadav,
  • Upasana Deori,
  • Upasha Acharyya,
  • Bahadur Sk and
  • Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

Graphical Abstract
  • -pTC and BPy-p3C exhibit lone-pair electrons at the pyridinyl nitrogen atom and show prominent emission in the solid and aggregated states. We therefore demonstrated the switching of fluorescence using acid and base vapors in neat film (Figure 6a and Figure 6c). Both emitters exhibited switching of the
  • fluorescence responses upon exposure to acidic and basic fumes on neat film (Figure 6a and Figure 6c). The intense green emission of the BPy-pTC film turned dark upon exposure to trifluoroacetic acid (TFA) vapor for 4 s (Figure 6a). The green fluorescence reappeared after neutralization with triethylamine (TEA
  • -p3C aggregates in 90 vol % water/THF mixture. Fluorescence switching by acid and base fumes exposure: Emission spectra (λex = 375 nm) of (a) BPy-pTC and (c) BPy-p3C in neat film upon exposure to TFA and TEA vapor at room temperature. Fluorescence switching by addition of TFA and KOH to (b) BPy-pTC and
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Published 08 Sep 2022

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

  • Dharmendra Das,
  • Akhil A. Bhosle,
  • Amrita Chatterjee and
  • Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

Graphical Abstract
  • reaction conditions was carried out using p-cresol (1a) as the model substrate with 1.1 equiv of N-bromosuccinimide (NBS) for attempted monobromination. They were ground together at the speed of 100 rpm in an electrical grinder (EG) of Agate-made under neat conditions for 30 min. The reaction was
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Published 09 Aug 2022

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

  • Nisha Devi and
  • Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

Graphical Abstract
  • functionalization of the β-carboline framework. Accordingly, 3-formyl-9H-β-carbolines 6a–e were subjected to MBH reaction with acrylonitrile A and various acrylates B–E under neat conditions in the presence of DABCO as depicted in Scheme 2. All the products were furnished smoothly in 27–72% yield. During this study
  • . For this purpose, the N-ethyl derivative 9e of 6e was prepared and subjected to MBH reaction with acrylonitrile A and methylacrylate B under neat conditions to generate the corresponding MBH adducts (10eA and 10eB) (Scheme 3). Interestingly, 9e showed more affinity towards this C–C bond forming
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Published 26 Jul 2022

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

  • Koji Kubota,
  • Emiru Baba,
  • Tamae Seo,
  • Tatsuo Ishiyama and
  • Hajime Ito

Beilstein J. Org. Chem. 2022, 18, 855–862, doi:10.3762/bjoc.18.86

Graphical Abstract
  • serve as reactants and solvents (neat liquid conditions). In addition, a long reaction time (12 h) is required to complete the reaction [15]. A general and efficient solvent-free borylation protocol that can be applied to liquid as well as solid aryl halides remains undeveloped. Recently
  • 3). Reactions with DPEphos and XPhos, which are the optimal ligands for neat liquid conditions reported by Nechaev [15], also yielded only poor results (Table 1, entries 4 and 5). Other monophosphine ligands, such as SPhos, PCy3, and PAd3, did not improve the yield of 3a (Table 1, entries 6–8). The
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Published 18 Jul 2022

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

  • Maxime Pypec,
  • Laurent Jouffret,
  • Claude Taillefumier and
  • Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

Graphical Abstract
  • proton exchange. Overall, the NMR study suggests that the N-methylamino glycine monomer and oligomers have a strong propensity to form intermolecular hydrogen bonds, an interesting and sought-after property for self-assembling and interaction with biological targets. Neat peptoids 1–6 were also
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Published 14 Jul 2022

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

  • Hengjia Liu and
  • Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

Graphical Abstract
  • /TFA 5000:1 (v/v); device C, neat film of compound 7. Figure 6a and 6b were reproduced from [37], P. Zalar et al., “Color Tuning in Polymer Light-Emitting Diodes with Lewis Acids”, Angew. Chem., Int. Ed., with permission from John Wiley and Sons. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA
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Published 12 Jul 2022

Synthesis of odorants in flow and their applications in perfumery

  • Merlin Kleoff,
  • Paul Kiler and
  • Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

Graphical Abstract
  • ) with molecular oxygen at elevated temperatures providing (+)-nootkatone (8) in 10% yield (Scheme 2). In this setup, neat (+)-valencene (7) is mixed with a stream of oxygen resulting in the formation of a segmented gas–liquid flow. In segmented flow a higher surface-to-volume ratio is achieved and
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Published 27 Jun 2022

Complementarity of solution and solid state mechanochemical reaction conditions demonstrated by 1,2-debromination of tricyclic imides

  • Petar Štrbac and
  • Davor Margetić

Beilstein J. Org. Chem. 2022, 18, 746–753, doi:10.3762/bjoc.18.75

Graphical Abstract
  • ), even with the agitation by ultrasound (Table 1, entry 22). The ratios of side-products vary depending on the reaction conditions (Table S1, Supporting Information File 1). The endo-product 15 was dominant in the neat grinding experiment (Table 1, entry 1), whereas phthalimide 16 dominates when NaCl was
  • could be also obtained by cycloaddition parity reversal principle [16][36], employing norbornene dibromide 11 and furan (18). Ball milling reaction without THF (neat grinding) provided 22 as the major product, together with a minor amount of dehalogenated product 40 (Scheme 2). When THF was added for
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Published 24 Jun 2022

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

  • Dajana Barišić,
  • Mario Pajić,
  • Ivan Halasz,
  • Darko Babić and
  • Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

Graphical Abstract
  • using N-halosuccinimides as the halogen source under neat grinding or liquid-assisted grinding conditions in a ball mill has been described. Depending on the azobenzene substrate used, halogenation of the C–H bonds occurs in the absence or only in the presence of PdII catalysts. Insight into the
  • -bromosuccinimide (NBS) under neat grinding (NG) and liquid-assisted grinding (LAG) conditions in a ball mill [51]. Insight into the dynamics of the formation of reaction intermediates and products was obtained by in situ Raman monitoring that provided information on the nature of the catalytically active PdII
  • product as a single isomer in both the catalyzed and uncatalyzed reactions. Neat grinding of L3 and L4 with NCS produced the monochlorinated products L3Cl-I and L4Cl-I as single isomers within one hour (Table 1, entries 2 and 3). In contrast, the reaction of L5 with NCS resulted in a mixture of mono- and
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Published 15 Jun 2022

New synthesis of a late-stage tetracyclic key intermediate of lumateperone

  • Mátyás Milen,
  • Bálint Nyulasi,
  • Tamás Nagy,
  • Gyula Simig and
  • Balázs Volk

Beilstein J. Org. Chem. 2022, 18, 653–659, doi:10.3762/bjoc.18.66

Graphical Abstract
  • 24 was accomplished in neat conditions within 3 days of reaction time using a literature procedure [5]. Attempts in acetonitrile as solvent were unsuccessful: after 1 day at room temperature, product 28 was isolated in only 20% yield, while at reflux temperature, a decomposition has been observed
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Published 10 Jun 2022

Sesquiterpenes from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346

  • Wiriya Yaosanit,
  • Vatcharin Rukachaisirikul,
  • Souwalak Phongpaichit,
  • Sita Preedanon and
  • Jariya Sakayaroj

Beilstein J. Org. Chem. 2022, 18, 479–485, doi:10.3762/bjoc.18.50

Graphical Abstract
  • mg) was then washed with acetone to afford compound 5 (3.7 mg). Trichocitrinovirene A (1): Colorless gum; +46.1 (c 0.67, MeOH); UV (MeOH) λmax, nm (log ε): 210 (3.32); ECD (MeOH, c 0.0008) λmax, nm (Δε): 227 (+4.3); IR (neat) νmax: 3336, 1684, 1649 cm−1; 1H and 13C NMR (CD3OD) see Table 1; HRMS–ESI
  • (m/z): [M + Na]+ calcd for C15H22O5Na, 305.1356; found, 305.1359. Trichocitrinovirene B (2): Colorless gum; +44.6 (c 0.67, MeOH); UV (MeOH) λmax, nm (log ε): 210 (3.67); IR (neat) νmax: 3386, 1683, 1645 cm−1; 1H and 13C NMR (CD3OD) see Table 1; HRMS–ESI (m/z): [M + Na]+ calcd for C15H22O6Na
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Published 29 Apr 2022

Trichloroacetic acid fueled practical amine purifications

  • Aleena Thomas,
  • Baptiste Gasch,
  • Enzo Olivieri and
  • Adrien Quintard

Beilstein J. Org. Chem. 2022, 18, 225–231, doi:10.3762/bjoc.18.26

Graphical Abstract
  • 1). Presence of TCA in the 1H NMR spectra is easily monitored through a broad peak around 9 ppm and also through the upfield migration of the other peaks of the amine ammonium salt. Heating the amine salt precipitate neat at 100 °C also provided partial decarboxylation (Table 1, entry 2). In sharp
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Published 24 Feb 2022

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

Graphical Abstract
  • solvent-tuned [129]. In neat CH2Cl2, the reaction produced the expected β-trichloromethyl alkyl azide; however, the reaction was chemoselective for diazidation when tert-butanol was used as co-solvent. The authors hypothesized the presence of the alcohol suppresses the polar-unmatched HAT process from
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Published 07 Dec 2021
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