Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

• Emese Gal,
• Luiza Gaina,
• Hermina Petkes,
• Alexandra Pop,
• Castelia Cristea,
• Gabriel Barta,
• Dan Cristian Vodnar and
• Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

• that the C-(hetero)aryl-α-(arylamino)acetonitrile derivatives can be considered genotoxically safe and possibly antimutagenic. Keywords: Ames test; α-aminoacetonitriles; ferrocene; phenothiazine; SEM; single crystal XRD; sonochemistry; Introduction Sonochemistry can be considered as a major

Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

• Alexander P. Molchanov,
• Mariia M. Efremova,
• Mariya A. Kryukova and
• Mikhail A. Kuznetsov

Beilstein J. Org. Chem. 2020, 16, 2679–2686, doi:10.3762/bjoc.16.218

• of azomethine imine, generated from pyrazolopyrazole 3g. Supporting Information Supporting Information File 422: Experimental and characterization data of all new compounds. Acknowledgements NMR, HRMS and XRD studies were performed at the Saint Petersburg State University Center for Magnetic

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

• (Table 1). As expected, an increase in the SSA was observed upon grinding because of the reduction of the β-CD particle size. XRD analysis X-ray diffraction data give additional evidence for the crystallinity variation of the β-CD particles upon grinding. Figure 3 shows a series of X-ray powder

• diffraction X-ray diffraction (XRD) measurements were performed using a Rigaku ULTIMA IV diffractometer equipped with Cu anticathode (λKα = 1.5418 Å), Soller slits to limit the divergence of X-ray beam and a nickel foil filter to attenuate the CuKβ line. XRD patterns were recorded in the range of 3–50° (scan

• modified CDs. Kinetics In a similar manner as described in [14]. SEM images of β-CD particles a) before grinding and ground for b) 5 min, c) 10 min, d) 29 min, e) 85 min, and f) 297 min. Granulometric composition of β-CD particles against time after grinding at 30 Hz. XRD patterns of β-CD powders obtained

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• afford much stronger coordination to Pd(II) than OH typically present in CNC, and potentially prevent its full reduction. Through FTIR (Supporting Information File 1, Figure S2) and XRD (Supporting Information File 1, Figure S3) analysis, there is little to no structural changes occurring in either the

• ChNC or the ChsNC during catalyst fabrication. The lack of metallic Pd peaks present in XRD is indicative of extreme broadening of the reflections of very small Pd NPs within the packets found. Heck coupling is a prominent reaction for arene alkenylation, as the production of stilbene derivatives is

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

• cyclization required extended heating in refluxing toluene and finally furnished the neutral polycycle 11 in good yield. The paddlewheel-shaped structure of 11 was established by an XRD structure determination and is shown in Figure 1. The reactivity of 1a in the Diels–Alder reaction with anthracene may be

• reaction mechanism. Thus, the reaction of 1a with α-methylstyrene or 1,1-diphenylethene proceeded at a faster rate than with styrene and yielded 3-methyl- and 3-phenyl-2-vinylindenes 12b and 12c (structure confirmed by an XRD analysis, see Figure 2) in high yields. Benzo[a]fluorenes were found to a minor

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation

• Kumar Godugu,
• Venkata Divya Sri Yadala,
• Mohammad Khaja Mohinuddin Pinjari,
• Trivikram Reddy Gundala,
• Lakshmi Reddy Sanapareddy and
• Chinna Gangi Reddy Nallagondu

Beilstein J. Org. Chem. 2020, 16, 1881–1900, doi:10.3762/bjoc.16.156

• pyridines via C–N, C–C, and C–S bond formations in a mixture of ethanol and H2O under ultrasound irradiation. The catalyst is characterized by XRD, FTIR, Raman spectroscopy, SEM, and EDAX analysis. The main advantages of this methodology include the wide substrate scope, cleaner reaction profile, short

• indicators. The catalyst was characterized by XRD, IR, Raman, SEM, and EDAX analysis. The chemical composition of the NDL was determined by adopting a standard quantitative analysis [75]. The obtained results are summarized in Table 1. The basic strength of the NDL catalyst (H_) was measured using Hammett

• 0.02 M benzoic acid solution. From the titer values of the benzoic acid solution, the amount of the basic sites was found to be 0.033 mmol/g. The powder XRD pattern of the NDL catalyst is shown in Figure 2. The diffraction peaks at 2θ = 23.16, 29.51, 31.05, 36.02, 38.07, 39.40, 43.0, 47.2, 47.5, 48.5

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

• Dominik Göbel,
• Marius Friedrich,
• Enno Lork and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2020, 16, 1683–1692, doi:10.3762/bjoc.16.139

• previous deprotection reactions, fluorene 21 was converted by means of a three-step sequence to the desired azide-functionalized 7-bromofluorene-2-carbaldehyde 5 in 86% yield and an overall yield of 45% (starting from fluorene). The molecular structure of 5 could be verified by X-ray diffraction (XRD, see

Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

• Csilla Hargitai,
• Györgyi Koványi-Lax,
• Tamás Nagy,
• Péter Ábrányi-Balogh,
• András Dancsó,
• Gábor Tóth,
• Judit Halász,
• Angéla Pandur,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136

• ) coupled with a Dionex Ultimate 3000 RS HPLC (Sunnyvale, CA, USA) system with a diode array detector. HRMS spectra of the diastereomeric 23a and 23b compounds are shown on page S44 of Supporting Information File 1. Single-crystal X-ray diffraction (SC-XRD) measurements were carried out on a Rigaku R-Axis

• Spider diffractometer (Tokyo, Japan) with imaging plate area detector using graphite monochromatic Cu Kα radiation. SC-XRD structures were deposited at the Cambridge Crystallographic Data Centre under the following numbers: CCDC 1953421 (3a), 1953424 (3b), 1953422 (8b), 1953423 (23a) and 1958809 (23b

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

• Gui-Feng Kang and
• Gang Zhang

Beilstein J. Org. Chem. 2020, 16, 1447–1455, doi:10.3762/bjoc.16.120

• structure unambiguously, as a representative example, the structure of 6aa was also confirmed by single crystal X-ray diffraction (XRD) studies after crystallization from ethyl acetate/hexane (Figure 2). CCDC 1991859 (for 6aa) contains the supplementary crystallographic data for this paper. These data are

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• /O elemental analysis, EDX, XPS, XRD and TGA. Keywords: activated carbon; catalysis; characterization techniques; metal supported on carbon catalysts; preparation methods; Introduction Support materials for metal catalysts allow the dispersion and stabilization of small metal particles on a surface

• phosphorous species in the carbons could be responsible for the examined difference [130]. X-ray diffraction (XRD): X-ray diffraction gives information on the crystallinity or amorphicity of activated carbons. Comparison of resulting XRD patterns with the crystallographic databases clarify that partially

• graphitic structures are available in the activated carbon materials. In addition, XRD can be used for investigations of the activation process by detecting crystalline intermediates of the activation reagents. Liang and co-workers found in the activated carbon prepared by microwave-induced ZnCl2 activation

Formal preparation of regioregular and alternating thiophene–thiophene copolymers bearing different substituents

• Atsunori Mori,
• Keisuke Fujita,
• Chihiro Kubota,
• Toyoko Suzuki,
• Kentaro Okano,
• Takuya Matsumoto,
• Takashi Nishino and
• Masaki Horie

Beilstein J. Org. Chem. 2020, 16, 317–324, doi:10.3762/bjoc.16.31

• fluoroalkyl group and a branched oligosiloxane unit in hexanes was noted. XRD analysis of the copolymer 6c, bearing branched oligosiloxane and methyl groups, was carried out. Two remarkable peaks were observed at 2θ = 3.94° and 12.18°, respectively, as shown in Figure 2a. The result suggested that the thin

• our result from the XRD analysis (7.3 Å) corresponding to the aggregation of the alternating methyl substituent [27]. Conclusion In summary, we showed that formally alternating thiophene–thiophene copolymers could be synthesized by employing differently substituted halobithiophenes as monomers in

• and KF-404HQ. Molecular weights and molecular weight distributions were estimated on the basis of the calibration curve obtained by 6 standard polystyrenes. UV–vis absorption spectra of the polymer films were measured with a Shimadzu UV-3150 spectrometer. XRD analysis was carried out with a Rigaku

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

• Sarah Kölsch,
• Heiko Ihmels,
• Jochen Mattay,
• Norbert Sewald and
• Brian O. Patrick

Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

• single crystals after slow evaporation, their structure was determined by single crystal X-ray diffraction (XRD) analysis (Figure 8, cf. Supporting Information File 1). The cyclobutane 4b crystallized from water in the monoclinic space group P21/n, and the derivative 4c crystallized from water in the

• triclinic space group . Both XRD analyses clearly showed that both cyclobutane products were formed as rctt configured dimers 4b and 4c (Figure 8). The products 4b and 4c may have formed by a syn head-to-tail dimerization of the E-configured substrate 3a and 3b or by an anti head-to-tail photodimerization

Carbazole-functionalized hyper-cross-linked polymers for CO₂ uptake based on Friedel–Crafts polymerization on 9-phenylcarbazole

• Dandan Fang,
• Xiaodong Li,
• Meishuai Zou,
• Xiaoyan Guo and
• Aijuan Zhang

Beilstein J. Org. Chem. 2019, 15, 2856–2863, doi:10.3762/bjoc.15.279

• of rough surface particles. The particles had different size and agglomerated to loose aggregates. There were plentiful pores randomly distributed among the particles. X-ray diffraction (XRD) of obtained HCPs exhibited similar diffraction patterns, only a round peak at 10°, hinting that P1–P11 were

• NETZSCH TG 209F1 TG analyzer for 40–800 °C at a heating rate of 10 °C min−1 under a nitrogen flow of 50 mL min−1. The X-ray diffraction (XRD) patterns of the as prepared polymers were collected using a PANalytical X’pert Pro MPD diffractometer with Cu Kα radiation at room temperature, with step size of

• 100% which was due to the adsorbed catalyst or solvent in the pore structure [15]. All obtained samples were colored ranging from pale brown to dark brown. FTIR spectrum of HCPs P1–P5 and 9-PCz. Solid state 13C NMR spectrum of P3. TGA curves of HCPs P1–P5. Scanning Electron micrograph of HCPs. The XRD

Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

• Nadezhda S. Demina,
• Nikita A. Kazin,
• Nikolay A. Rasputin,
• Roman A. Irgashev and
• Gennady L. Rusinov

Beilstein J. Org. Chem. 2019, 15, 2678–2683, doi:10.3762/bjoc.15.261

• suitable for XRD analysis (Figure 2). Conclusion In summary, in this study, we showed the convenience of the Fiesselmann thiophene synthesis for the construction of new aryl-substituted thieno[3,2-b]thiophene derivatives, namely the reaction of 5- or 4-aryl-3-chlorothiophene-2-carboxylates with methyl

A photochemical determination of luminescence efficiency of upconverting nanoparticles

• Baptiste Amouroux,
• Clément Roux,
• Jean-Claude Micheau,
• Fabienne Gauffre and
• Christophe Coudret

Beilstein J. Org. Chem. 2019, 15, 2671–2677, doi:10.3762/bjoc.15.260

• volatile solvents removal, (iii) the high temperature crystallization step for 90 minutes. Spherical nanoparticles of 21.8 ± 1.3 nm were collected. Crystal quality was assayed by XRD and only the hexagonal β-phase could be detected (Supporting Information File 1). These particles are kept well dispersed in

• knowing NYb the number of ytterbium per nanoparticle: NYb and NEr (NEr: number of erbium atom per particles) can be derived from the number of RE atoms per NP, itself computed from TEM and XRD measurements taking into account the nanoparticles size (volume ≈ 5400 ± 1000 nm3), unit cell volume (107.6 Å3

1,5-Phosphonium betaines from N-triflylpropiolamides, triphenylphosphane, and active methylene compounds

• Vito A. Fiore,
• Chiara Freisler and
• Gerhard Maas

Beilstein J. Org. Chem. 2019, 15, 2603–2611, doi:10.3762/bjoc.15.253

• XRD analysis (vide supra), the stereochemistry at the P-substituted olefinic bond could be determined in all cases from characteristic chemical shifts of the olefinic proton and from 3J(P,H) and 3J(P,C) coupling constants. The olefinic proton signal of the E-isomers was found in the δ range 6.8–7.7

• acid chlorides. Two mechanistic scenarios for the formation of betaines 3. Resonance structures describing the bonding in 1,2-oxaphospholes/1,5-betaines 8. Bond distances and torsion angles in betaines E-3a, E-3b, E-3e, and Z-3e based on XRD data.a Selected NMR data of betaines 3a. Supporting

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

Installation of -SO₂F groups onto primary amides

• Jing Liu,
• Shi-Meng Wang,
• Njud S. Alharbi and
• Hua-Li Qin

Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186

• converted to the corresponding N-fluorosulfonyl amides and only a mixture of undesired products were observed. Interestingly, during the work-up process of drying 2e with Na2SO4, a colourless crystal 4e was observed and its structure was confirmed by XRD analysis (Scheme 3). We speculate that the

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• crucial cyclization steps to the stable and soluble fused systems were achieved by copper-catalyzed C–S and C–Se coupling/cyclization reactions. Structures and packing motifs in the solid state were elucidated by single crystal X-ray analysis and XRD powder measurements. Comparison of the optoelectronic

• 45–52%) and a mixture of both, parallel and antiparallel stacked dimers, were found in the X-ray structure analysis of heterotriacenes 2 (Figure S6b,c) and 4 (Figure S8b and S8c in Supporting Information File 1), respectively. XRD powder measurements For completion, we performed XRD measurements on

• microcrystalline powders of all derivatives (Supporting Information File 1, Figure S9). At first glance, the stronger intensity of the signals for DTT 1 and DST 3 clearly evidences a higher crystallinity compared to triacenes DTS 2 and DSS 4. XRD plots of heterotriacenes 1 to 3 obtained from the corresponding

Mechanochemical synthesis of hyper-crosslinked polymers: influences on their pore structure and adsorption behaviour for organic vapors

• Sven Grätz,
• Sebastian Zink,
• Hanna Kraffczyk,
• Marcus Rose and
• Lars Borchardt

Beilstein J. Org. Chem. 2019, 15, 1154–1161, doi:10.3762/bjoc.15.112

• protocol the polymer obtained through this mechanochemical route is also amorphous as visualized by the XRD (X-ray diffraction) patters recorded (Supporting Information File 1, Figure S1) [43]. Furthermore, NG-HCP similarly shows a high thermal stability with a decomposition onset in air (Supporting

Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• , Xiangnan University, Chenzhou 423000, China 10.3762/bjoc.15.97 Abstract The fabrication of electrospun nanofibers comprising cucurbit[7]uril (CB[7]) and poly(ε-caprolactone) (PCL) is reported. Various techniques such as SEM, FTIR, XRD, DSC and TG were utilized to characterize the morphology, composition

• dispersion and crystallization of CB[7] and PCL in the composite nanofibers, XRD patterns of neat PCL nanofibers and all PCL/CB[7] nanofibers were recorded (Figure 2). PCL is a semi-crystalline polymer, and neat PCL nanofibers elicit two strong and sharp characteristic diffraction peaks at 2θ = 22° and 2θ

• = 24.5° which correspond to (110) and (200) reflections, respectively [12][15][17]. On the other hand, there are two wider diffraction peaks at 2θ = 13° and 2θ = 21.2° in the XRD curve of CB[7] powders. From the XRD curves of the PCL/CB[7] nanofibers, the sharp diffraction peaks of PCL and wide

Fabrication of supramolecular cyclodextrin–fullerene nonwovens by electrospinning

• Hiroaki Yoshida,
• Ken Kikuta and
• Toshiyuki Kida

Beilstein J. Org. Chem. 2019, 15, 89–95, doi:10.3762/bjoc.15.10

• structurally amorphous fiber materials consistently [9][11]. In this work, we expected that the incorporation of C60 into γ-CD nanofibers helps with the regular arrangement of γ-CD molecules, but γ-CD–C60 microfiber materials do not also show a specific XRD pattern (Figure S8 in Supporting Information File 1

• Information Supporting Information File 2: UV–vis and viscosity measurements of the spinning solutions, electrospinning at various parameters, and XRD patterns of the prepared nonwovens. Acknowledgements This research was financially supported by a research fund from Kondo Memorial Foundation and a Grant in

MoO₃ on zeolites MCM-22, MCM-56 and 2D-MFI as catalysts for 1-octene metathesis

• Hynek Balcar,
• Martin Kubů,
• Naděžda Žilková and
• Mariya Shamzhy

Beilstein J. Org. Chem. 2018, 14, 2931–2939, doi:10.3762/bjoc.14.272

• –Grubbs type hybrid catalysts active in metathesis of long-chain unsaturated esters [24]. Results and Discussion Catalyst preparation and characterization XRD patterns and texture properties (Table 1, Figure 1 A,B,C,D) of prepared MCM-22, MCM-56 and 2D-MFI zeolites proved a high quality of these supports

• already observed earlier [9][10][24]. For x MoO3/MCM-22(28), XRD patterns of catalysts are similar to those of their parents approximately up to x = 6 wt % of Mo (0.9 Mo atoms per nm2). At higher Mo concentrations signals of crystalline MoO3 appeared (marked with * in Figure 1 A,B,D). It suggests 6 wt

• , catalysts with 6 wt % (and lower) content of Mo did not exhibit any MoO3 signals. It is consistent with the previous observation that MoO2(acac)2 provided better catalyst than MoO3 [9]. XRD patterns of 6MoO3/MCM-56(13) and 6MoO3/2D-MFI(26) indicated also a good MoO3 spreading, contrary to 6MoO3/HZSM-5(25

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• minutes at 70 °C, a dark green soiled salt was obtained in 98% yield. The catalyst was characterized by different analyses. The FE-SEM images exhibited that the particles of the catalyst are in nano size. According to XRD pattern, the crystallite size is at about 13.7 nm. The IR spectrum confirmed the

Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

• Lidia A. Smyshliaeva,
• Mikhail V. Varaksin,
• Pavel A. Slepukhin,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2018, 14, 2618–2626, doi:10.3762/bjoc.14.240

• be attributed to C-2 of the imidazole ring. The structure of imidazolyl carborane 5d has also been proved by the X-ray analysis (Figure 3). The single crystals were obtained by slow evaporation of imidazolyl carborane 5d from a mixture of CH2Cl2/heptane, 8:2. According to the XRD data, two