One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

• Juan Lu,
• Bin Yao,
• Desheng Zhan,
• Zhuo Sun,
• Yun Ji and
• Xiaofeng Zhang

Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171

• eliminating the intermediate purification. It is an efficient way to build up novel spirooxindolepyrrolothiazoles for drug discovery screening. Bioactive Spirooxindole-pyrrolothiazoles. Graphical representation of the green metrics (AE, AEf, CE, RME, OE and MP) analysis for processes A and B. The higher the

• value, the greener the process. Graphical representation of the green metrics (PMI, E-factor, and SI) analysis for processes A and B. The lower value, the better the reaction process. The diastereoselective synthesis of spirooxindoles through MCRs. The synthesis of spirooxindolepyrrolothiazoles. Four

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• with compound 8. (B) Viral load quantification by real-time PCR after treatment with compound 8. Superposition of the top-ranked docking solution of compound 8 (carbon atoms in yellow, in stick representation) with the crystallographic poses of IMP and inhibitor MAD1 (color by atoms in stick

• representation) inside the IMPDH active site from Mycobacterium tuberculosis (cartoon representation – PDB code 4ZQP), with selected residues and interactions here also represented. Synthesis of 1-azido-3-nitrobenzene (c). Synthesis of the triazole-substituted triterpene derivatives 7 and 8. Antiviral activity

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• noticeably from each other. ORTEP representation of triferrocenyl trithiophosphite showing 50% probability thermal ellipsoids. Optimized conformations and relative energies of four possible conformers of triferrocenyl trithiophosphite. Calculated NBO charges on the Fe ions and hydrogen atoms for the

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• -tetraazaadamantane motif in X-ray structures of the obtained N-TAAD derivatives (representation of non-hydrogen atoms as thermal ellipsoids at 50% probability level). Anions and crystal-solvate molecules are omitted for clarity. (a) 4a·HCl·H2O·MeOH. (b) 4c·HCl·3.5MeOH. (c) Bn-4c·3CD3OD (bromide salt). (d) 8a. (e

• ) 19e·3HCl·H2O. (f) 21·HCl·2H2O. (a) General structure of host–guest complexes of 3N-TAADs with water. (b) The general structure of host–guest complexes of 3N-TAADs with methanol. (c) Host–guest motif in the X-ray structure of 4a·HCl·H2O·MeOH (guest molecule is shown in “spacefill” representation). (d

• ) Host–guest motif in the X-ray structure of 4c·HCl·3.5MeOH (guest molecule is shown in “spacefill” representation). (e) Hirshfeld surface of the TAAD cation in 4a·HCl·H2O·MeOH. (e) Hirshfeld surface of the TAAD cation in 4c·HCl·3.5MeOH. (a) Dynamic processes in TAADs 4 and complexation with ROH. (b

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

• mechanochemical reactions occur. As a result, the field of mechanochemistry as a whole will ultimately be strengthened. Representation of (a) cavitation and elongational flow caused by pulsed ultrasonication, (b) mixer mill, (c) planetary ball mill, and (d) ring-and-puck mill (vibrating disc mill). Structure of

• cellulose and chitin and approximation to the structure of lignin. Tensile forces by ball milling change the conformation of a chitin model compound. This deformation facilitates the subsequent cleavage of glycosidic bonds to produce oxocarbenium ion intermediates for hydrolysis [45]. (a) Representation of

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

• Daniele Rocco,
• Ana A. Folgueiras-Amador,
• Richard C. D. Brown and
• Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

• NMR (CDCl3) δ 7.73 (d, J = 16.0 Hz, 1H), 7.56–7.49 (m, 2H), 7.45–7.31 (m, 8H), 6.49 (d, J = 16.0 Hz, 1H), 5.26 (s, 2H) ppm; 13C NMR (CDCl3) δ 166.8, 145.2, 136.1, 136.0, 134.3, 130.4, 128.9, 128.6, 128.29, 128.26, 128.1, 117.9, 66.4 ppm. Schematic representation of a plane-parallel plate flow

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

• substituted frameworks. A summary of previous reports toward exploration of 3-formyl-9H-β-carbolines. Library of C-3-substituted pyrido[3,4-b]indole MBH derivatives 7, 8 and 10. Results of optimization for fluorescence studies: a) contact time; b) concentration; c) solvent. Pictorial representation of

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• cycloadditions of tetrasubstituted azomethine ylides with cyclopropenes. ORTEP representation of the molecular structure of 3e. Early studies concerning cyclopropene cycloadditions to azomethine ylides and cycloaddition reactions involving protonated Ruhemann's purple (PRP). The pilot experiment aimed at

Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

• Zhihang Bai,
• Krishnasamy Velmurugan,
• Xueqi Tian,
• Minzan Zuo,
• Kaiya Wang and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

• UV light. Proposed mechanism for the 2-bromo-1-phenylethanone dehalogenation reaction mediated by m-TPEWP5G-EsY nanoassembly as a photocatalyst. Graphical representation of the fabrication of supramolecular m-TPEWP5G-EsY self-assembled photocatalytic system. Products from 2-bromo-1-phenylethanone

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• NPs. EDX spectrum of the Ni–chitosan NPs. Synthesis of dialkyl 1,4-dihydropyridine-2,3-dicarboxylate derivatives. ORTEP representation of product 4a (CCDC 1949329). Recycling experiment of the Ni–chitosan nanocatalyst. A plausible mechanistic route for the synthesis of C5–C6-unsubstituted 1,4-DHP

The enzyme mechanism of patchoulol synthase

• Houchao Xu,
• Bernd Goldfuss,
• Gregor Schnakenburg and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 13–24, doi:10.3762/bjoc.18.2

• products of patchoulol synthase (4–12). ORTEP representation of patchoulol (3). Cu Kα, Flack parameter: −0.1(2); P2(true) = 1.000, P3(false) = 0.6·10−5). Energy profile from DFT calculations (Gibbs energies at 298 K, mPW1PW91/6-311 + G(d,p)//B97D3/6-31G(d,p)) for the three mechanisms of 3 biosynthesis by

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• three main conformations of the macrocycle in P5 cis (column A) and P5 trans (column B) shown in liquorice. Aliphatic hydrogen atoms are hidden and a ribbon representation of the peptidic backbone is shown in grey. Other amino acids in the sequence are not shown in the figure although present in the

• given next to the respective structure and backbone-atoms root mean square deviation with respect to the active conformation are indicated in parenthesis. RMSD reported and used in clustering were calculated from Pro to Met only. A schematic representation of the secondary structure of each amino acid

Adjusting the length of supramolecular polymer bottlebrushes by top-down approaches

• Tobias Klein,
• Franka V. Gruschwitz,
• Maren T. Kuchenbrod,
• Ivo Nischang,
• Stephanie Hoeppener and
• Johannes C. Brendel

Beilstein J. Org. Chem. 2021, 17, 2621–2628, doi:10.3762/bjoc.17.175

• obtain some control over the length distributions of 1D polymer nanostructures, and thus this makes them more likely to be applied in biomedicine, where dimensional control is a prerequisite. Schematic representation of the chemical structures of BTU and BTP and the supramolecular self-assembly of the

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

In-depth characterization of self-healing polymers based on π–π interactions

• Josefine Meurer,
• Julian Hniopek,
• Johannes Ahner,
• Michael Schmitt,
• Jürgen Popp,
• Stefan Zechel,
• Kalina Peneva and
• Martin D. Hager

Beilstein J. Org. Chem. 2021, 17, 2496–2504, doi:10.3762/bjoc.17.166

• polymer, indicating a reversible cause for the shifts. Additionally, all bands exhibit broadening during heating, especially noticeable at 150 °C, indicating a broader distribution of species contributing to the IR spectrum. Schematic representation of the first healing of P1 at 150 °C. Schematic

• representation of the polymer synthesis of P1 and P2. Overview of the healing of P1. Supporting Information Supporting Information File 368: Additional data. Funding The authors would like to thank the Deutsche Forschungsgemeinschaft (DFG, HA606/7-1 and 36459901 – Collaborative Research Center (CRC) “CataLight

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

• Sumana Mandal,
• Raju D. Chaudhari and
• Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

• toxicity concerns, Hg(II) salts are cheap, stable, and versatile in terms of reactivity, making them a viable option to similar transition metal catalysts. Schematic representation of Hg(II)-mediated addition to an unsaturated bond. First report of Hg(II)-mediated synthesis of 2,5-dioxane derivatives from

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

• Li Liu,
• Yue Li,
• Tiao Huang,
• Dulin Kong and
• Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

• industrial application. Representation of bioactive molecules and applications. Synthetic methodologies for 3-monohalooxindoles. Substrate scope of the acidolysis of isatin-derived phosphates 2 with hydrochloric acid. Standard reaction conditions: 2a–r (0.5 mmol), respectively, hydrochloric acid (7.5 mmol

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• docking results were edited using the Visual Molecular Dynamics 1.9.3 (VMD) program (available for download at http://www.ks.uiuc.edu/Research/vmd/vmd-1.9.3/). Proposed structural modifications to obtain triazole derivatives 1a, b and 2a–j. Asymmetric unit representation of the 1,2,3-triazole derivative

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• on the elemental analysis, the authors provided the formula representation C10H6(I2)0.4 for PAZ-I2 and C10H4.9(Br2)0.72 for PAZ-Br2. The gel permeation chromatography (GPC) analysis of the tetrahydrofuran (THF)-soluble fraction of PAZ-Br2 indicated the presence of oligomeric species (average degree

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• exposed PCL fibers in the PHEMA-filled MEW scaffolds. Schematic representation of the self-initiated photografting and photopolymerization (SIPGP) of 2-hydroxyethyl methacrylate (HEMA) including intersystem crossing from singlet to triplet state which is mandatory for the formation of a biradical (left

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

• Zara M. Seibel,
• Jeffrey S. Bandar and
• Tristan H. Lambert

Beilstein J. Org. Chem. 2021, 17, 2077–2084, doi:10.3762/bjoc.17.134

• organizational interactions. This complexity makes the detailed prediction of the transition state organization for the current process very challenging. However, we propose that the general structure 19 shown in Figure 3 is a reasonable representation of one of the likely pathways (the major ambiguities being

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• aminoethoxy moiety at the 2’-position (Figure 2B), thus creating a monomer that could further stabilize the triplex [128]. In theory, this strategy allows for fewer modifications to be used in designing ASOs with high RNA target affinities. A schematic representation of 16-mer ASOs in different designs. White