Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• gram-scale preparation was carried out using 1a, that afforded the desired product in 96% yield (Scheme 4, reaction 4). To gain more insight into the reaction mechanism, several control experiments were carried out (Scheme 5). On one hand, the failure of substrates 10–15 to participate in the reaction

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• landscape of [2 + 2] CA–RE reactions for the preparation of push–pull chromophores is rapidly evolving and expanding. This evolution necessitates an update on the latest insights for materials science researchers. Furthermore, the diverse research advancements related to the distinctive physicochemical

Preparing a liquid crystalline dispersion of carbon nanotubes with high aspect ratio

• Keiko Kojima,
• Nodoka Kosugi,
• Hirokuni Jintoku,
• Kazufumi Kobashi and
• Toshiya Okazaki

Beilstein J. Org. Chem. 2024, 20, 52–58, doi:10.3762/bjoc.20.7

• ) absorption measurements were carried out using a Fourier-transform infrared spectroscopy (Bruker, VERTEX 80v) and a THz time domain spectroscopy (THz-TDS) system (Otsuka Electronics, TR-1000). Preparation of the DWCNT dispersion The dispersion of DWCNTs was prepared using a two-step process in accordance

• were sealed by UV resin. After the samples were left for one week, the liquid phases were observed using an OLYMPUS BX51 polarized optical microscope (POM). Preparation and characterization of DWCNT film The DWCNT film was prepared from the dispersion with nematic phase by bar-coating method. Initially

NMRium: Teaching nuclear magnetic resonance spectra interpretation in an online platform

• Luc Patiny,
• Hamed Musallam,
• Alejandro Bolaños,
• Michaël Zasso,
• Julien Wist,
• Metin Karayilan,
• Eva Ziegler,
• Johannes C. Liermann and
• Nils E. Schlörer

Beilstein J. Org. Chem. 2024, 20, 25–31, doi:10.3762/bjoc.20.4

• ]. Thus, the first part of data handling, i.e., processing and preparation of an interpretation-ready state of spectra, is insufficiently treated in education. In the same way, the export format of evaluated/assigned experiments remains vague [36], and adequate recent developments for electronic

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• formal cycloaddition reaction of readily available heterocyclic azides with 3,3-diaminoacrylonitriles. The reaction represents a novel method for the preparation of 1,2,3-triazoles bearing an N-hetaryl amidine moiety and thus this reaction offers a novel method for the preparation of new types of 1

• ethyl 2-cyanoacetimidate and corresponding amines according to the literature procedure [17] and compounds 1a,c–e,h–j are commercially available. Azides 2a–d,f,g were synthesized according to the literature procedures [18][19][20][21][22][23], and azide 2e is commercially available. Preparation of

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF₃: the case of alkyne hydration. Chemistry vs electrochemistry

• Marta David,
• Elisa Galli,
• Richard C. D. Brown,
• Marta Feroci,
• Fabrizio Vetica and
• Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

• complex organic compounds, widely used both in organic chemistry and in electrochemistry as raw materials for the preparation of different molecules of pharmaceutical and industrial interest [1][2][3][4][5][6][7][8][9]. Among the different organic transformations involving alkynes, their hydration is a

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• report described the preparation of a CAAC·CS2 zwitterion. Thus, in 2009 Bertrand et al. obtained the betaine 2 by reacting the free carbene 1 with a slight excess of CS2 in THF at room temperature (Scheme 1) [62]. The starting material that featured a bulky and rigid spirocyclic alkyl group derived from

Studying specificity in protein–glycosaminoglycan recognition with umbrella sampling

• Mateusz Marcisz,
• Sebastian Anila,
• Margrethe Gaardløs,
• Martin Zacharias and
• Sergey A. Samsonov

Beilstein J. Org. Chem. 2023, 19, 1933–1946, doi:10.3762/bjoc.19.144

• ligand from its bound position and allowing the ligand to approach the protein from a very distant position to the binding sites. Materials and Methods Structures and parameters Ligand preparation GAG structures used in the study consist of two parts: 1. the part from the experimental structure (heparin

• 1C4 conformation for the IdoA2S ring was chosen as it was shown to be the essentially dominant conformation in the microsecond scale simulations performed by Sattelle et al. as it is energetically more favorable than the 2SO conformation [40]. Complex preparation The obtained ligands were docked using

Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• readily available reagents, mild conditions, satisfactory yields, broad substrate scope, high molecular convergence, and atomic economy. The synthetic applications of this annulation reaction in heterocyclic chemistry might be significant. Experimental General procedure for the preparation of dihydrospiro

• , 125.5, 117.4, 109.9, 95.0, 52.3, 44.4, 37.0, 20.9 ppm; IR (KBr) ν: 2960, 2936, 2870, 2211, 1717, 1626, 1498, 1445, 1367, 1268, 1193, 1112, 1090, 1009, 903, 868, 815 cm−1; HRMS–ESI TOF (m/z): [M + Na]+ calcd for C34H26N4O2Na, 545.1956; found, 545.1948. General procedure for the preparation of

• , 127.5, 127.0, 124.4, 111.6, 110.4, 52.2, 51.1, 44.4, 36.8 ppm; IR (KBr) ν: 2924, 2853, 1721, 1608, 1484, 1456, 1430, 1340, 1170, 812 cm−1; HRMS–ESI TOF (m/z): [M + H]+ calcd for C34H27ClN3O4, 576.1685; found, 576.1683. General procedure for the preparation of dihydrospiro[indoline-3,5'-[1,2]diazepines

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• -dibora-2,5-cyclohexadiene structure (Scheme 16) in addition to a π-extended linear POA (Scheme 17) [50]. The preparation of v- and z-shaped POAs 77 and 78 was carried out starting from 2-bromobiphenylene (74). Initial steps involved ortho-directed lithiation and subsequent treatment with Me3SiCl

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• /V∙s at the electric field of 8.1 × 105 V/cm (Figure 8). Conclusion Synthetically convenient protocols for the preparation of sophisticated pyridine-3,5-carbonitriles containing carbazole substituents in positions 2 and 6 were developed starting with 4-bromobenzaldehyde. The compounds were found to

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• dithranol as the matrix. Optical absorption spectra were recorded using a Pyrex cell with a 10 mm path length and a spectrophotometer (V-670; Jasco Corp.). Preparation of La@C2v-C82 As described in [19], soot containing endohedral metallofullerenes were produced through the standard arc vaporization method

• in the second step. Preparation of the La@C2v-C82 anion As described in [21], La@C2v-C82 (0.34 × 10−6 mol) was dissolved in 10 mL of a pyridine solution containing TBAF (0.54 × 10−3 mol) and then stirred for 2 h under an Ar atmosphere. The resulting green solution was concentrated to 2.0 mL. CS2 was

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• ]. This approach also supports that the solution-processable OLED application is a perfectly suitable device preparation for DMB-TT-TPA (8). Thermal properties The thermal properties of DMB-TT-TPA (8) were investigated through thermal gravimetric analysis (TGA) at 750 °C at a heating rate of 10 °C min−1

• . The high thermal stability is profitable for the preparation of stable and durable OLED devices. Computational chemistry Ground-state geometry optimization of DMB-TT-TPA (8) was performed using density functional theory (DFT) calculations with the Gaussian 16 software at the B3LYP/6-31G (d,p) level

N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

• Grigory Kantin,
• Pavel Golubev,
• Alexander Sapegin,
• Alexander Bunev and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

• the preparation of modified glutarimides with a wide range of aromatic and aliphatic NH-heterocycles under mild conditions in moderate to high yields. It is shown that electron-rich substrates tend to give C–H insertion products. The N-modification of tetrazoles and 1,2,4-triazoles using a

• )-catalyzed N–H-insertion reaction. Preparation of diazo reagent 5. Scope of NH insertion reaction of N-Boc-α-diazo glutarimide and various N-heterocycles. aIsolated yield; reaction scale ‒ 0.33 mmol of NH-heterocycle, 0.4 mmol of diazo reagent 5, catalyst ‒ 2.5 mM Rh2(esp)2 in DCM, 100‒300 μL (0.06‒0.18 mol

• %); bNMR yield; cstructure confirmed by single-crystal X-ray data; dcalculated yield based on incomplete conversion of NH-substrate. Examples of N-deprotection of α-modified glutarimides 1. Preparation of NH2-containing derivative 10 via reduction of 6n. Supporting Information Deposition number 2298240

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• % ee). Moreover, 1 mol % of the catalyst was feasible to conduct the gram-scale preparation of baclofen precursor (89% yield, 96% ee). Finally, thanks to the lipophilic character of the catalyst, it was easily recycled after the reaction by replacing the non-polar reaction solvent with a polar solvent

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• 4e against S. aureus provides a good lead for further structural optimizations. Preparation of α-(o-nitrobenzoyl)-β-enamino amides 3. Reagents and conditions: i) EtNH2 (70% aq, 1.05–1.15 equiv), CH2Cl2, Na2SO4, 24 h, rt; ii) NMM (1 equiv), DMAP (0.2 equiv), o-nitrobenzoyl chloride (1 equiv), CH2Cl2

Active-metal template clipping synthesis of novel [2]rotaxanes

• Cătălin C. Anghel,
• Teodor A. Cucuiet,
• Niculina D. Hădade and
• Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

• beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation

• synthesis of the axle unit (compound 6 in Scheme 1) we considered a convergent synthetic approach that consist in preparation of the stopper, functionalized with azide groups, decoration of the central pyridine-based moiety with propargyl groups and their connection by CuAAC click chemistry. Thus, as

• the yields displayed by the two strategies for the preparation of reference macrocycles M1 (20%) and M2 (44%) [44]. The 1H NMR spectrum of [2]rotaxane R2 displayed signals corresponding to both axle and macrocycle in a 1:1 ratio (see Supporting Information File 1, Figure S19 for the full NMR spectrum

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• used as a chloride source for the preparation of these compounds [50] (Scheme 8b). As early as in 1982, the reactivity of trifluoromethylated hydrazonoyl halides in the presence of base has been systematically studied by Tanaka et al. The trifluoromethylated hydrazonoyl halides, as the precursors of

• oxidation/cyclization with NXS or Cu(OAc)2. Notably, some of the resultant CF3-substituted 1,6-dihydropyridazines exhibited aggregation-induced emission [102][103] (Scheme 16). The hydrocyanation of acylhydrazones is an important method for the preparation of α-hyrazino acids. Hu et al. reported a Lewis

• acid-catalyzed hydrocyanation of trifluoromethylated acylhydrazones, in which the product was the precursor for the preparation of chiral fluorinated amino acids [104] (Scheme 17a). Meanwhile, Hu et al. provided a novel and efficient process for the synthesis of polysubstituted 3-trifluoromethyl-1,2,4

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• and therefore more conformationally rigid compounds. Previously, the unintentional preparation of two polyunsaturated 1,2,4,8,9,11-hexaazamacrocycles fused with two benzene or two pyrazole rings has been reported [39][40]. In particular, Dolzhenko et al. attempted to reproduce the synthesis of 4-imino

• EtOH, and NaOH in water (Scheme 1). The key intermediate of the macrocycle preparation, imidate 4, was synthesized using the reported procedure [43] by refluxing a solution of aminopyrazole 3 in triethyl orthoformate. First, we studied the reaction of imidate 4 with hydrazine hydrate in EtOH under

• useful for the preparation of other polyunsaturated annulated 14-membered 1,2,4,8,9,11-hexaazamacrocycles. Experimental All solvents and liquid reagents purchased from commercial sources were distilled prior to use. Petroleum ether had a distillation range of 40–70 °C. 100% Hydrazine hydrate was used in

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• stability in aqueous medium. Thus, the electronic absorption spectra of hdz-CH3 and hdz-NO2 were recorded in a 10% DMSO/buffer solution (pH 7.4) immediately after preparation and at regular time intervals. The UV–vis spectrum of hdz-CH3 between 250 and 450 nm (Figure 6A) shows two multicomponent absorptions

• × 10−3 mol L−1. Dilutions (5 × 10−5 mol L−1) were prepared in DMSO/buffer (50 × 10−3 mol L−1) in a 10:90 (v/v) ratio and kept at 25 °C during the whole experiment. Spectra were recorded immediately after preparation of the solutions and at defined time intervals. The changes in absorbance intensity

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• a powerful tool for polymer crosslinking and preparation of materials with enhanced properties. 3.3 Polymer surface modification When modifying the surface of polymers, chemical selectivity typically plays a minor role, while harsh reaction conditions are useful for the modification of chemically

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• sulforhodamine B were purchased from Sigma-Aldrich, USA. 4-Amino-3-hydroxy-1-naphthalene sulfonic acid was purchased from Fluka, India. Sulfuric acid was purchased from ACROS Organics, Belgium and diethyl ether was purchased from VWR-Prolabo Chemicals, Belgium. Liposomes preparation, extrusion, and purification

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

• isolation of fungi, B.Y.G.M., E.G.M.A. and Y.M.-F.; formal analysis, B.M.K., and F.S.; investigation, B.Y.G.M., E.G.M.A. and Y.M.-F.; writing–original draft preparation, B.Y.G.M., E.G.M.A., S.F.K. and M.S.; writing–review and editing, S.F.K., and M.S.; supervision, S.F.K. and M.S.; project administration

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• desired derivatives. Unexpected oxidation side-product B2, B4, and B6 were also isolated from certain reaction mixtures. Direct modification of the original berberine structure. Preparation of non-cyclic charged variants of B1. Partial reduction of compound B1 to B14. Synthesis of the substituted 2