A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• the application in parallel synthesis and combinatorial chemistry. Experimental Typical procedure for the GBB multicomponent reaction. To a solution of 2-aminopyridine (1a, 0.5 mmol), 2-ethynylbenzaldehyde (2a, 0.5 mmol), and tert-butylisocyanide (3, 0.6 mmol) in 1 mL of methanol were added p

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• the form of a downstream located cartridge [97]. Honeycomb (or foam) catalysts consist of inert carrier materials with millimetre size parallel channels (or cavities) obtained by extrusion, onto which a catalytically active layer is deposited, usually a porous inorganic oxide bonded to the support

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• demonstrated with these two parallel reports for hollow-green and solid blue-emitting CDs. A systematic study has been performed by the Travas-Sejdic group on the synthesis of CDs from either citric acid or glucose starting materials in the presence of either TTDDA or dopamine, in order to evaluate how the

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• vibration is observed on the SAM PM-IRRAS spectra at 1153 cm−1. Therefore, by application of the strict IRRAS dipole selection rules, the SO2 group should be oriented parallel to the surface. The PM-IRRAS spectrum of 4-ATP on gold is shown in Figure 2b and is dominated by a band at 1627 cm−1 assigned to

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• -phenylamino-1,3,4-thiadiazolium chloride (2.05/3.00 Å [36]). In the packing arrangement of the crystal, the chloride ions are found in anion channels oriented along the 21 screw axis parallel to the crystallographic a-axis of the orthorhombic unit cell (space group P212121). The molecular shape of the cation

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• the crude coupling reaction mixtures. 1H NMR spectrum of 2–β-CD with partial assignment (DMSO-d6, 600 MHz, 298 K). Size distributions of 1 mM aqueous solutions of conjugates 4–β-CD (a) and 2–β-CD (b) at 25.0 °C (pH 7) by intensity (three parallel measurements: blue, green and red lines). Normalized

Investigation of the action of poly(ADP-ribose)-synthesising enzymes on NAD⁺ analogues

• Sarah Wallrodt,
• Edward L. Simpson and
• Andreas Marx

Beilstein J. Org. Chem. 2017, 13, 495–501, doi:10.3762/bjoc.13.49

• automodification. If analogues are successfully incorporated, the polymer chains can additionally be detected in the fluorescence read-out. For a better comparison, ARTD1-based ADP-ribosylation assays were also performed, because all four analogues have never been tested in parallel before. The outcome of these

• amounts of modified PAR was formed with the 6-modified derivative 2 and in the absence of natural NAD+ (Supporting Information File 1, Figure S1, lane 7 and Figure S2, lane 5), when compared in parallel with 2-modified analogue 1. However, a strong signal is detected in a mixture containing NAD+ (Figure

Adsorption of RNA on mineral surfaces and mineral precipitates

• Elisa Biondi,
• Yoshihiro Furukawa,
• Jun Kawai and
• Steven A. Benner

Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42

• minerals, with baryte > celestine > gypsum (59% > 49% > 20%) (Table 2). Constraints of natural mineralogy However, and as a limitation of this approach, many minerals that might be made in the laboratory have no known natural correlates that we can examine in parallel. For example, in the synthetic borate

• with liquid evaporation and by incubating the mineral pieces at 25, 37, 55, 75, or 95 °C in a sterile environment for 2 hours. In parallel, the same amounts of RNA were incubated at the same temperatures in 1.5 mL low-binding test tubes. After incubation, RNA adsorbed to aragonite surfaces, or adhering

Continuous N-alkylation reactions of amino alcohols using γ-Al₂O₃ and supercritical CO₂: unexpected formation of cyclic ureas and urethanes by reaction with CO₂

• Emilia S. Streng,
• Darren S. Lee,
• Michael W. George and
• Martyn Poliakoff

Beilstein J. Org. Chem. 2017, 13, 329–337, doi:10.3762/bjoc.13.36

• ). For this reaction, self-optimisation is important as multiple products were identified that could form in parallel; from 1 the possible products we expected to see were a mixture of piperidine (2a), N-methylpiperidine (2b), N- and O-methylated 1, as well as oligomers. We chose to target 2b only for

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

• Yi Lai,
• Zhijian Zong,
• Yujie Tang,
• Weimin Mo,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen,
• Liqun Jin,
• Wen-hua Sun and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

• modifications [1][2][3][4]. The achievement is largely beneficial to organic chemists for their parallel contributions in Pd-catalyzed transformations as well as for discovering new reactions. The improvement of the efficiency of noble metal catalysts is still highly attractive from both the academic and the

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• both stock solutions and VR the volume of the flow reactor. Running the plate reactor at 160 °C (Table 3, entry 3.9), we managed to achieve a production capacity of 116.3 g/h, which equates to an S.T.Y. of 1.11 kg L−1 h−1. Parallel to the scale-up in the plate flow reactor, we also scaled up the

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• natural logarithmic scale as a function of time linear relationships were obtained proving the first order kinetics of degradation. The regression coefficients were in the range of 0.98–1.00. Three parallel measurements were evaluated. Determination of methylene blue concentration The concentration of the

Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

• Mathew J. Jones,
• Ricardo Callejo,
• Alexandra M. Z. Slawin,
• Michael Bühl and
• David O'Hagan

Beilstein J. Org. Chem. 2016, 12, 2823–2827, doi:10.3762/bjoc.12.281

• considerably wider (≈116°) than that of the C–CH2–C angles (≈112°), which is now recognised as a general phenomenon of the CF2 group in an aliphatic chain/ring [10][11][12][13]. The two axial fluorines flex away from each other with widened right angles of 96.3°, distorting a co-parallel orientation. This

The digital code driven autonomous synthesis of ibuprofen automated in a 3D-printer-based robot

• Philip J. Kitson,
• Stefan Glatzel and
• Leroy Cronin

Beilstein J. Org. Chem. 2016, 12, 2776–2783, doi:10.3762/bjoc.12.276

• be remedied by ‘numbering up’ the reaction vessels that the robotic platform prints in the initial stage and adjusting the control software such that several reactions could be run in parallel to increase the yield of ibuprofen. Once the reaction sequence had been completed the final reaction mixture

• ’ approach to chemical synthesis itself where synthetic routines can be downloaded and tested by any laboratory with the necessary robotic platform, advances in the chemical automation equipment could then run in parallel with advances in the synthetic strategies used. Finally, this work shows how chemical

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

• identify a subset of possible drug compounds. Small molecules that are predicted to bind to the target with high affinity can be identified. These “hits” are then generally further optimized and subsequently tested experimentally. With improving computational resources and parallel processing cluster

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• lowest acidic pKa values are predominant in physiological environment, which is also indicated by the difference of log D values between pH 7.4 and pH 6.5. The blood–brain barrier (BBB) specific penetration of dracocephins isomers has also been studied by the PAMPA (parallel artificial membrane

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

• Florin Albota,
• Mino R. Caira,
• Constantin Draghici,
• Florea Dumitrascu and
• Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

• 104 crystal structures that contain the sydnone moiety. Of these, eleven were found to display the same anti-parallel sydnone–sydnone motif as is occurring in 9d (Figure 2b), reflecting the dipolar alignment of these moieties consistent with the positive charge centered on the ring and the negative

Facile synthesis of indolo[3,2-a]carbazoles via Pd-catalyzed twofold oxidative cyclization

• Chao Yang,
• Kai Lin,
• Lan Huang,
• Wei-dong Pan and
• Sheng Liu

Beilstein J. Org. Chem. 2016, 12, 2490–2494, doi:10.3762/bjoc.12.243

• dibromobenzoic acid with sulfuric acid in methanol) with an excess of anilines in the presence of cesium carbonate and catalytic quantities of Pd(OAc)2 and BINAP were processed smoothly. The desired methyl 2,4-dianilinobenzoates (2a–e) were obtained in good to excellent yield. In a parallel synthesis, using the

Inhibition of peptide aggregation by means of enzymatic phosphorylation

• Kristin Folmert,
• Malgorzata Broncel,
• Hans v. Berlepsch,
• Christopher H. Ullrich,
• Mary-Ann Siegert and
• Beate Koksch

Beilstein J. Org. Chem. 2016, 12, 2462–2470, doi:10.3762/bjoc.12.240

• between glutamates and lysines. Intermolecular coulombic interactions between e and g direct the monomers into a parallel dimeric orientation. The solvent-exposed position f is occupied by serine for better solubility. One site of each position b, c, and f contains valine, making the system prone to

• experiment with PKA. Helical wheel projection of two parallel helical strands and primary structure of KFM6. The recognition motif KFM6(20–24) for PKA is given in bold and valine residues are bold and underlined. Supporting Information Supporting Information File 490: Description of further methods and

Methylenelactide: vinyl polymerization and spatial reactivity effects

• Judita Britner and
• Helmut Ritter

Beilstein J. Org. Chem. 2016, 12, 2378–2389, doi:10.3762/bjoc.12.232

• with EMP narrow dispersity was achieved (Đ = 1.6). This dispersity of 1.6 illustrates the upper limit for a successful RAFT process. Beside the good dispersity, the Mn in comparison to the theoretical value Mn theo. is much higher due to the known parallel running process of self-initiation. For this

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

• Martin Obst and
• Burkhard König

Beilstein J. Org. Chem. 2016, 12, 2358–2363, doi:10.3762/bjoc.12.229

• . The reaction was carried out by rotation of the glass rod (80 rpm) and parallel irradiation with the 455 nm LEDs for 24 hours. After the reaction, the product was isolated by flash column chromatography (gradient of ethyl acetate in petroleum ether). 4,4’-Dimethoxybenzophenone (1b) 1H NMR (300 MHz

• the glass rod (80 rpm) and parallel irradiation with the 455 nm LEDs for 24 hours. After the reaction, the product was isolated by flash column chromatography (gradient of ethyl acetate in petroleum ether). Trial 1: 4-Methoxyphenyl methyl carbinol (82.2 mg, 0.54 mmol) and RFTA (14.0 mg, 0.03 mmol

Enantioconvergent catalysis

• Justin T. Mohr,
• Jared T. Moore and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2016, 12, 2038–2045, doi:10.3762/bjoc.12.192

• reactive intermediates. Three important types of enantioconvergent catalysis are specifically discussed herein: type I – stereomutative, type II – stereoablative [8], and type III – parallel kinetic resolution [9]. The primary criteria for all enantioconvergent catalytic reactions are: The starting

• control the formation of asymmetric carbons on each fragment. The doubly stereoconvergent nature of this reaction represents one of the most complex examples of stereoablative enantioconvergent catalysis to date. Type III: Enantioconvergent parallel kinetic resolution A third approach to enantioconvergent

• powerful parallel kinetic resolution (PKR) strategy [32][33], owing to the two parallel processes occurring simultaneously. Although PKR reactions significantly increase the observed product ee relative to a simple kinetic resolution system, the theoretical maximum yield for a traditional PKR is still

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

• Jacob R. Hauser,
• Hester A. Beard,
• Mary E. Bayana,
• Katherine E. Jolley,
• Stuart L. Warriner and
• Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

• . Calorimetry experiments were carried out using HEL AutoMATE parallel reactors with HEL WinISO 2225 and HEL IQ 1.2.16 software. Temperature was controlled using a Julabo refrigerated/heating circulator (Model FP50-HD) and feed reactants introduced into the reaction using a Harvard syringe pump (model pump 11

Unusual reactions of diazocarbonyl compounds with α,β-unsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N–H-insertion products

• Valerij A. Nikolaev,
• Jury J. Medvedev,
• Olesia S. Galkina,
• Ksenia V. Azarova and
• Christoph Schneider

Beilstein J. Org. Chem. 2016, 12, 1904–1910, doi:10.3762/bjoc.12.180

• in the yields of up to 50% (Table 2, entries 5–9) in parallel with the Wolff rearrangement product 6с (18–79%; Table 2, entries 4–7). The structures of these compounds were established by 1H and 13C NMR, 2D NMR (H,H-COSY, HMBC, HSQC) spectra, as well as by comparison with the literature data in the

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

• Valeria Corne,
• Ariel M. Sarotti,
• Carmen Ramirez de Arellano,
• Rolando A. Spanevello and
• Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

• moieties lie parallel to each other, and the distances from the centroid of the aromatic ring to the midpoint of the C=C double bond are in the range of 3.25–3.31 Å, consistent with the distances for other π-stacked systems [2]. On the other hand, in the anti conformers the remoteness of the phenyl and