Table of Contents
143	Full Research Paper
21	Letter
31	Review
1	Commentary

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

Renata Kaczmarek,
Dariusz Korczyński,
James R. Green and
Roman Dembinski

Letter
Published 02 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Preparation of (2'-deoxy)-5-alkynyluridines 2 and 3, their dicobalt hexacarbonyl derivatives 4 and 5...
  
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3. Figure 1: Structures of nucleosides 6 and 7, products of the Nicholas reaction.
  
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Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

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Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose

Lukáš Kerner and
Paul Kosma

Full Research Paper
Published 02 Jan 2020

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1. Graphical Abstract
2. Figure 1: Modification of lipid A by ArnT.
  
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3. Scheme 1: Phosphonate and glycal synthesis.
  
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4. Scheme 2: Synthesis of methyl phosphonate 11 and octyl phosphonates 16 and 17.
  
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Beilstein J. Org. Chem. 2020, 16, 9–14, doi:10.3762/bjoc.16.2

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Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction

Damian Kusy,
Agata Wojciechowska,
Joanna Małolepsza and
Katarzyna M. Błażewska

Full Research Paper
Published 03 Jan 2020

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1. Graphical Abstract
2. Figure 1: Substrates used for the Mizoroki–Heck reaction in this study.
  
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3. Figure 2: Structures of the identified side products 4 and 5.
  
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4. Scheme 1: Scope of the method for analogs derived from 1 and 2. The ratio of isomers is given (E/Z or β/α) in...
  
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5. Scheme 2: Dealkylation of fluorinated analog 23 under the Mizoroki–Heck reaction conditions.
  
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Beilstein J. Org. Chem. 2020, 16, 15–21, doi:10.3762/bjoc.16.3

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Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

Andreas H. Heindl and
Hermann A. Wegner

Full Research Paper
Published 03 Jan 2020

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1. Graphical Abstract
2. Figure 1: 1,3,5-Tris(arylazo)benzenes as individually switchable multistate photoswitches: previous [11,12] and pres...
  
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3. Scheme 1: Synthetic strategy towards 1,3,5-tris(arylazo)benzenes 3 based on consecutive Baeyer–Mills reaction...
  
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4. Scheme 2: Preparation of tris(arylazo)benzenes 3 by Pd-catalyzed cross-coupling reactions of N-Boc-arylhydraz...
  
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5. Scheme 3: Synthesis of azobenzene building block 8.
  
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6. Scheme 4: Synthesis of 1,3-bis(4-methoxyphenylazo)-5-phenylazobenzene (14).
  
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7. Scheme 5: Synthesis of unsymmetrical tris(arylazo)benzenes 3a/3b using Pd-catalyzed coupling reactions and Cu...
  
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8. Scheme 6: Coupling reactions of 15 with the corresponding arylhydrazides to access monocoupled (16a/16b) and ...
  
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9. Figure 2: a) UV–vis spectra of tris(arylazo)benzenes 3a/3b in ethanol. b) Reversible photoisomerization of 3a...
  
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Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

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Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

María C. Mollo,
Natalia B. Kilimciler,
Juan A. Bisceglia and
Liliana R. Orelli

Full Research Paper
Published 06 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Chemical shift data for N-thiobenzoylpiperidine and compound 4a.
  
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3. Scheme 2: PPSE promoted ring closure reactions of amido- and thioamido alcohols.
  
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Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

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Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

Sergii Afonin,
Oleg Babii,
Aline Reuter,
Volker Middel,
Masanari Takamiya,
Uwe Strähle,
Igor V. Komarov and
Anne S. Ulrich

Full Research Paper
Published 07 Jan 2020

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1. Graphical Abstract
2. Figure 1: DAE photoswitch and photoswitchable peptides explored in this study. (A) The reversible photoisomer...
  
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3. Figure 2: Two versions of the D. rerio embryotoxicity assay for DAE-modified peptides: timelines, peptide pho...
  
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4. Figure 3: The in vivo toxicity against D. rerio embryos appears to be correlated with the empirical hydrophob...
  
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5. Figure 4: D. rerio embryotoxicity of GS 1 and the photoswitchable analogues 2–20 correlated with their in vit...
  
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6. Figure 5: Phototherapeutic cytotoxic action against HeLa cells of GS 1 and its photoswitchable analogues 2–20...
  
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Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

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Understanding the role of active site residues in CotB2 catalysis using a cluster model

Keren Raz,
Ronja Driller,
Thomas Brück,
Bernhard Loll and
Dan T. Major

Full Research Paper
Published 08 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Mechanism for formation of cyclooctat-9-en-7-ol, published similarly in [42].
  
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3. Figure 1: Computed electronic energy profiles (kcal/mol) for the CotB2 cyclase mechanism. The calculations us...
  
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4. Figure 2: Intermediates A–I in the active site model. Interactions are marked by dashed orange lines, the int...
  
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5. Figure 3: TS structures TS_A_B–TS_G/H_I in the active site model. Interactions are marked by dashed orange li...
  
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6. Figure 4: Comparison between gas phase and active site model conformations. A) Intermediate D. B) Intermediat...
  
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Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7

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Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

Sabrina Müller,
Jannik Paulus,
Jochen Mattay,
Heiko Ihmels,
Veronica I. Dodero and
Norbert Sewald

Full Research Paper
Published 09 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Pyrrole–imidazole–azobenzene polyamides and the dsDNA target sequences employed in this study.
  
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3. Scheme 2: Building blocks required for the synthesis of the photoswitchable Im/Py polyamides. A) Fmoc–Azo–OH 1...
  
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4. Figure 1: Section of the ¹H NMR (600 MHz) spectrum of polyamide P1. A) Initial thermal equilibrium. B) After ...
  
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5. Figure 2: E/Z isomer ratio of the polyamides P1–P3. Values were obtained from the respective ¹H NMR experimen...
  
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6. Figure 3: Titration experiments of target DNA sequences with P1–P3 in the photostationary Z-state and the the...
  
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7. Figure 4: Titration of DNA containing single mutations (in bold) with P1–P3 in the photostationary Z-state an...
  
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Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

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The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

Xiaodong Zhang,
Jun Xie,
Zhiling Xu,
Zhu Tao and
Qianjun Zhang

Full Research Paper
Published 10 Jan 2020

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1. Graphical Abstract
2. Figure 1: Chemical structures of baicalein (left), cucurbit[8]uril (right).
  
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3. Figure 2: The possible interaction model for Q[8] and baicalein.
  
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4. Figure 3: ¹H NMR spectra (400 MHz) of Q[8] (a), baicalein (b) and BALE–Q[8] (1:1) (c) recorded in DCl.
  
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5. Figure 4: The absorption spectra of BALE upon the addition of Q[8] under different conditions [10 mol·L⁻¹ HCl...
  
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6. Figure 5: IR spectra of Q[8] (a), BALE (b), a physical mixture of Q[8]-BALE (N_Q[8]/N_BALE = 1:1) (c) and the B...
  
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7. Figure 6: DTA spectra of BALE (a), Q[8] (b), a physical mixture Q[8]-BALE (N_Q[8]/N_BALE = 1:1) (c) and the BAL...
  
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8. Figure 7: The stability curve of UV–vis absorption obtained for an isoconcentration of BALE and the BALE–Q[8]...
  
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9. Figure 8: The phase solubility graph obtained for BALE in Q[8] at λ = 270 nm.
  
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10. Figure 9: The clearance rate curve (A) and clearance time curve (B) of ABTS^+· upon increasing the concentrati...
  
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11. Figure 10: The release curves of BALE and BALE–Q[8].
  
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Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

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Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

Xingyu Xu,
Shiqing Huang,
Zengyu Zhang,
Lei Cao and
Xiaoyu Yan

Full Research Paper
Published 13 Jan 2020

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1. Graphical Abstract
2. Figure 1: 1,2,3-Triazole based XB donors: 1,2,3-triazole A, 1,2,3-triazolium B, 1,2,3-triazolylidene C and di...
  
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3. Scheme 1: Synthesis of 4,5-diiodo-1,3-dimesityl-1,2,3-triazolium with iodide, Mes: 2,4,6-Me₃C₆H₂.
  
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4. Scheme 2: Synthesis of 4,5-diiodo-1,3-dimesityl-1,2,3-triazolium with different anion.
  
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5. Figure 2: Packing structure of 2-I (top), 2-Br (middle) and 2-Cl (bottom). Hydrogen atoms have been omitted f...
  
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6. Figure 3: Packing structure of 2-BF₄. Hydrogen atoms have been omitted for clarity.
  
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7. Figure 4: Packing structure of 2-OAc. Hydrogen atoms and solvent molecules have been omitted for clarity.
  
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8. Figure 5: Packing structure of 2-TFA. Hydrogen atoms and disorder of fluorine atoms have been omitted for cla...
  
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9. Figure 6: Packing structure of 2-I^.1.5I₂. Hydrogen atoms have been omitted for clarity.
  
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10. Figure 7: Packing structure of 2-I^.3.5I₂. Hydrogen atoms have been omitted for clarity.
  
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11. Figure 8: Packing structure of 2-BF₄^.0.5bpy. Hydrogen atoms and dichloromethane have been omitted for clarity....
  
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12. Figure 9: 1,2,3-Triazole-based halogen model calculation: electrostatic potential surfaces mapped on total de...
  
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Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

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[1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

Katarzyna Włodarczyk,
Piotr Borowski and
Marek Stankevič

Full Research Paper
Published 21 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Arbusov, phospha-Fries, and phospha-Brook rearrangements.
  
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3. Scheme 2: Cyclization of 1a and 1b under acidic conditions.
  
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4. Scheme 3: The synthesis of P-stereogenic β-hydroxyalkylphosphine sulfides.
  
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5. Scheme 4: Cyclization of 8 and 19 in the presence of H₃PO₄.
  
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6. Scheme 5: Cyclization of (S_P)-19 in the presence of H₃PO₄.
  
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7. Figure 1: ¹H NMR spectra of compounds 12 and 29.
  
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8. Figure 2: ¹³C NMR spectra of compounds 12 and 29.
  
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9. Scheme 6: Synthesis of the alkenylphosphine sulfides used in study.
  
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10. Scheme 7: The reaction of mesylate compounds with Lewis-acidic AlCl₃.
  
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11. Scheme 8: The reaction of alkenylphosphine sulfides with AlCl₃.
  
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12. Scheme 9: Rearrangement of 20 in the presence of Brønsted acid. The calculated energies next to the arrows ar...
  
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13. Scheme 10: Rearrangement of 20 in the presence of Lewis acid. The calculated energies next to the arrows are r...
  
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14. Scheme 11: The synthesis of chiral substrates for rearrangement reactions.
  
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15. Scheme 12: The reaction of (S_P)-60 and (S_P)-65 with AlCl₃.
  
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16. Scheme 13: Reaction of chiral β-hydroxyalkylphosphine sulfides with Brønsted acid.
  
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17. Scheme 14: Attempted cyclization of enantiomerically enriched 53 and 46.
  
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Beilstein J. Org. Chem. 2020, 16, 88–105, doi:10.3762/bjoc.16.11

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Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

Tapasi Manna,
Arin Gucchait and
Anup Kumar Misra

Full Research Paper
Published 22 Jan 2020

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1. Graphical Abstract
2. Figure 1: Structure of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escheri...
  
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3. Scheme 1: (a) NIS, HClO₄/SiO₂, MS 4 Å, CH₂Cl₂, −45 °C, 1 h, 79%; (b) 0.1 M CH₃ONa, CH₃OH, room temperature, 2...
  
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4. Scheme 2: (a) HClO₄/SiO₂, CH₂Cl₂, −10 °C, 1 h, 76%.
  
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5. Scheme 3: (a) NIS, HClO₄/SiO₂, MS 4 Å, CH₂Cl₂, −40 °C, 1 h, 22%.
  
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6. Scheme 4: (a) NIS, HClO₄/SiO₂, MS 4 Å, CH₂Cl₂, −45 °C, 1 h, 74%; (b) BnBr, NaOH, TBAB, THF, room temperature,...
  
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Beilstein J. Org. Chem. 2020, 16, 106–110, doi:10.3762/bjoc.16.12

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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

Full Research Paper
Published 23 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of styrylquinolizinium derivatives 3a–d.
  
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3. Figure 1: Absorption spectra and normalized emission spectrum (Abs. = 0.10, 3b: λ_ex = 394 nm) of derivatives ...
  
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4. Figure 2: Spectrophotometric titration upon the addition of ct DNA to the styrylquinolizinium derivatives 3a ...
  
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5. Figure 3: Spectrofluorimetric titration upon the addition of ct DNA to the styrylquinolizinium derivatives 3a...
  
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6. Figure 4: CD and LD spectra of the styryl derivatives 3a (A), 3b (B), 3c (C), and 3d (D) with ct DNA in BPE b...
  
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7. Figure 5: Spectrophotometric monitoring of the irradiation of styrylquinolizinium derivatives 3a (A), 3b (B), ...
  
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8. Figure 6: Absorption of the monomers (c = 20 µM, red) 3b (A) and 3c (B) and their dimers (black) 4b and 4c in...
  
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9. Figure 7: Photometric monitoring of the photoreaction of 3b (c = 20 µM) to the dimer 4b by irradiation at ca....
  
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10. Figure 8: ORTEP drawings of cyclobutane derivatives 4b (A) and 4c (B) in the solid state (thermal ellipsoids ...
  
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11. Scheme 2: Possible pathways for the selective photodimerization of styrylquinolizinium derivatives 3b and 3c.
  
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12. Figure 9: A) Spectrophotometric titration of ct DNA to dimer 4b in BPE buffer (c_L = 20 µM, c_{ct DNA} = 1.45 mM, ...
  
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13. Figure 10: A) Photometric and B) CD spectroscopic monitoring of the photoinduced switching (4b: λ_ex = 315 nm, ...
  
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14. Scheme 3: Photoinduced switching of the DNA binding properties of styrylquinolizinium compound 3b.
  
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Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

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Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

Alexander Sailer,
Franziska Ermer,
Yvonne Kraus,
Rebekkah Bingham,
Ferdinand H. Lutter,
Julia Ahlfeld and
Oliver Thorn-Seshold

Full Research Paper
Published 27 Jan 2020

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1. Graphical Abstract
2. Figure 1: a) The potent tubulin inhibitor colchicine as a lead scaffold led to the development of the HOTub g...
  
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3. Figure 2: Chemical structures of HITubs. Key variations with respect to HITub-4 are highlighted in dashed box...
  
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4. Figure 3: Photocharacterisation of HITub-4. a) Photochemical and thermal isomerisation. b) UV–vis spectra aft...
  
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5. Figure 4: a) Resazurin reduction assay for HITub-4 and nocodazole in HeLa cells (n = 3), demonstrating the di...
  
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6. Figure 5: Confocal microscopy images of immunofluorescently labelled MT networks after treatment with HITubs ...
  
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7. Figure 6: Cell cycle analysis of HITub-4-treated cells. a) and b) (Z)-HITub-4 caused significant G2/M arrest ...
  
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Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

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Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

Thomas J. Cogswell,
Craig S. Donald and
Rodolfo Marquez

Full Research Paper
Published 28 Jan 2020

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1. Graphical Abstract
2. Figure 1: Aza-goniothalamin 1, (R)-(+)-goniothalamin 2 and acylated aza-goniothalamin analogue 3 [14-18].
  
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3. Scheme 1: One pot synthesis of benzyl carbamate 4 reported by Veenstra and co-workers [19].
  
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4. Scheme 2: Formation of diene 5 in 66% through a one pot, three component coupling.
  
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5. Scheme 3: Optimized conditions for the synthesis of diene 5.
  
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6. Scheme 4: Ring-closing metathesis reaction of diene 5 to yield dihydropyridone 7 [20-23].
  
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7. Figure 2: Extension of the two-pot methodology to include a variety of different aldehyde starting materials.
  
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8. Scheme 5: Total synthesis of aza-goniothalamin 1.
  
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Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

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Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

Abhijit Paul,
Debnath Chatterjee,
Srirupa Banerjee and
Somnath Yadav

Full Research Paper
Published 29 Jan 2020

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1. Graphical Abstract
2. Figure 1: Biologically and medicinally important 3-alkenylindoles.
  
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3. Scheme 1: a) Previous and b) present work related to the synthesis of 3-alkenylindoles.
  
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4. Scheme 2: Substrate scope for the C–H alkenylation of the indoles 1. Reaction conditions: 1 (1 mmol), 2 (2 mm...
  
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5. Scheme 3: a) Three-phase test to determine a homogeneous or heterogeneous catalytic mechanism of action for t...
  
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6. Scheme 4: Probable catalytic mechanism for the transformation of 1a by the RuNC.
  
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Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

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Synthesis, liquid crystalline behaviour and structure–property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes

Afef Mabrouki,
Malek Fouzai,
Armand Soldera,
Abdelkader Kriaa and
Ahmed Hedhli

Full Research Paper
Published 31 Jan 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of oxadiazole derivatives 2 and 4.
  
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3. Scheme 2: Tautomeric equilibrium of compound 3.
  
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4. Figure 1: DSC thermograms of fluorinated compounds 2b, 4a and 4b recorded at 5 °C/mn at heating (down traces)...
  
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5. Figure 2: Optical texture (×10) of liquid crystal phase for fluorinated compounds, (a): SmA phase observed in...
  
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6. Figure 3: Typical diffractogram observed for compound 2b at 398 K.
  
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7. Figure 4: Typical diffractogram observed for compound 4a at 411 K.
  
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8. Figure 5: Conformer of lowest energy of compounds: 4c, conformation A, (a) front view, (a’) top view, (a”) si...
  
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9. Figure 6: Vector of dipole moment of compounds 4c, 4b and 2b.
  
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10. Figure 7: Plot of molecular dipole moments. Orange, fluorocarbon compounds; blue, hydrocarbon compounds; gree...
  
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Beilstein J. Org. Chem. 2020, 16, 149–158, doi:10.3762/bjoc.16.17

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The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Narasimhamurthy Rajeev,
Toreshettahally R. Swaroop,
Ahmad I. Alrawashdeh,
Shofiur Rahman,
Abdullah Alodhayb,
Seegehalli M. Anil,
Kuppalli R. Kiran,
Chandra,
Paris E. Georghiou,
Kanchugarakoppal S. Rangappa and
Maralinganadoddi P. Sadashiva

Full Research Paper
Published 03 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of carbamothioates from xanthate esters and benzyl isocyanides.
  
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3. Figure 1: Substrate scope for the synthesis of carbamothioates. Reaction conditions for methods A and B: sodi...
  
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4. Figure 2: ORTEP diagram of O-benzyl (4-fluorobenzyl)carbamothioate (4c).
  
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5. Figure 3: Rotamers of thionocarbamates 4 (top) and computer-minimized structures of 4c (bottom).
  
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6. Scheme 2: Proposed general reaction mechanism for the formation of carbamothioates (e.g., 4a) from xanthate e...
  
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7. Figure 4: Optimized geometries of the reactants, transition states, intermediates, and products of the propos...
  
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8. Figure 5: Relative energies of the reactants, transition states (TS1–TS3), and intermediates (Int1–Int3) of t...
  
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Beilstein J. Org. Chem. 2020, 16, 159–167, doi:10.3762/bjoc.16.18

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Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

Jucleiton J. R. Freitas,
Queila P. S. B. Freitas,
Silvia R. C. P. Andrade,
Juliano C. R. Freitas,
Roberta A. Oliveira and
Paulo H. Menezes

Full Research Paper
Published 04 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Scope of the propargylation reaction. Reactions were performed with the appropriate aldehyde (1 mmo...
  
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3. Scheme 2: Synthesis of potassium allenyltrifluoroborate (4).
  
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4. Scheme 3: Propargylation of aldehydes using potassium allenyltrifluoroborate (4).
  
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Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

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The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds

Itamar L. Gonçalves,
Rafaela R. da Rosa,
Vera L. Eifler-Lima and
Aloir A. Merlo

Full Research Paper
Published 06 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Amines 3, 4, 8, 9, 12 and 13 installed on 5-membered isoxazoline and isoxazole rings.
  
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3. Scheme 2: Synthesis of acylisoxazolinylthioureas 17a–c and acylisoxazolylthioureas 18a–c. (i) SOCl₂, reflux, ...
  
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4. Scheme 3: Synthesis of amides. Part A: (i) SOCl₂, reflux; (ii) KOCN, acetone, reflux; (iii) amines 3, 4, 8 an...
  
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5. Figure 1: Optical textures observed on POM for thioureas 17a (a), 17b (b), 18a (c), 18b (d) and 18c (e,f). Al...
  
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6. Figure 2: Optical textures observed on POM of amide 19. (a) Fan-shaped focal conic texture of the SmA mesopha...
  
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7. Figure 3: DSC curves for the thiourea 17a (A), amide 19 (B) and 20 (C) upon the first heating and cooling cur...
  
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8. Figure 4: TGA analysis for thiourea 18c; and amides 20 and 22.
  
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Beilstein J. Org. Chem. 2020, 16, 175–184, doi:10.3762/bjoc.16.20

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Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

Akihiro Yuasa,
Kazunori Nagao and
Hirohisa Ohmiya

Letter
Published 07 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Our strategy.
  
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3. Scheme 2: Allylic cross-coupling using aldehydes as α-alkoxyalkyl anions.
  
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4. Scheme 3: Substrate scope and reaction conditions. a) reactions were carried out with 1 (0.4 mmol), 2 (0.2 mm...
  
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5. Scheme 4: Stoichiometric reaction.
  
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6. Scheme 5: Possible pathway.
  
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Beilstein J. Org. Chem. 2020, 16, 185–189, doi:10.3762/bjoc.16.21

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Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

Vuyisa Mzozoyana,
Fanie R. van Heerden and
Craig Grimmer

Full Research Paper
Published 10 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin (6).
  
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3. Figure 1: ¹H NMR spectra for the “aromatic” region of coumarin 6; comparison of ¹H spectrum and ¹H-{¹⁹F} spec...
  
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4. Figure 2: ¹³C NMR spectra for coumarin 5 and 6; showing the splitting of the signal corresponding to C5.
  
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5. Figure 3: ¹⁹F,¹H-HOESY NMR spectrum for coumarin 6 illustrating two through-space interactions.
  
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6. Figure 4: Superposition of single-crystal X-ray structure (red) and DFT-optimized structure (green); RMSD 0.3...
  
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7. Figure 5: DFT-optimized structure for coumarin (6).
  
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8. Figure 6: Plots of relative energy (black trace, no units), interatomic distance F–H5 (red trace, Å), interat...
  
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9. Figure 7: Short contacts within the single-crystal X-ray structure of coumarin 6.
  
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Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

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Combination of multicomponent KA² and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

Riccardo Innocenti,
Elena Lenci,
Gloria Menchi and
Andrea Trabocchi

Full Research Paper
Published 12 Feb 2020

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1. Graphical Abstract
2. Figure 1: Chemical structure of representative approved drugs containing a spirocyclic moiety.
  
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3. Scheme 1: Synthetic strategies for accessing pyrrolocyclopentenone derivatives, including the novel couple/pa...
  
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4. Scheme 2: Couple/pair approach using combined KA² and Pauson–Khand multicomponent reactions.
  
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5. Scheme 3: Follow-up chemistry on compound 5 taking advantage of the enone chemistry. Reaction conditions. (i)...
  
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6. Figure 2: Top: Selected NOE contacts from NOESY 1D spectra of compound 36; bottom: low energy conformer of 36...
  
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7. Figure 3: PCA plot resulting from the correlation between PC1 vs PC2, showing the positioning in the chemical...
  
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8. Figure 4: PMI plot showing the skeletal diversity of compounds 3–39 (blue diamonds) with respect to the refer...
  
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Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

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Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

Delphine Pichon,
Jennifer Morvan,
Christophe Crévisy and
Marc Mauduit

Review
Published 17 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Competitive side reactions in the Cu ECA of organometallic reagents to α,β-unsaturated aldehydes.
  
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3. Scheme 2: Cu-catalyzed ECA of α,β-unsaturated aldehydes with phosphoramidite- (a) and phosphine-based ligands...
  
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4. Scheme 3: One-pot Cu-catalyzed ECA/organocatalyzed α-substitution of enals.
  
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5. Scheme 4: Combination of copper and amino catalysis for enantioselective β-functionalizations of enals.
  
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6. Scheme 5: Optimized conditions for the Cu ECAs of R₂Zn, RMgBr, and AlMe₃ with α,β-unsaturated aldehydes.
  
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7. Scheme 6: CuECA of Grignard reagents to α,β-unsaturated thioesters and their application in the asymmetric to...
  
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8. Scheme 7: Improved Cu ECA of Grignard reagents to α,β-unsaturated thioesters, and their application in the as...
  
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9. Scheme 8: Catalytic enantioselective synthesis of vicinal dialkyl arrays via Cu ECA of Grignard reagents to γ...
  
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10. Scheme 9: 1,6-Cu ECA of MeMgBr to α,β,γ,δ-bisunsaturated thioesters: an iterative approach to deoxypropionate...
  
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11. Scheme 10: Tandem Cu ECA/intramolecular enolate trapping involving 4-chloro-α,β-unsaturated thioester 22.
  
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12. Scheme 11: Cu ECA of Grignard reagents to 3-boronyl α,β-unsaturated thioesters.
  
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13. Scheme 12: Cu ECA of alkylzirconium reagents to α,β-unsaturated thioesters.
  
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14. Scheme 13: Conversion of acylimidazoles into aldehydes, ketones, acids, esters, amides, and amines.
  
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15. Scheme 14: Cu ECA of dimethyl malonate to α,β-unsaturated acylimidazole 31 with triazacyclophane-based ligand ...
  
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16. Scheme 15: Cu/L13-catalyzed ECA of alkylboranes to α,β-unsaturated acylimidazoles.
  
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17. Scheme 16: Cu/hydroxyalkyl-NHC-catalyzed ECA of dimethylzinc to α,β-unsaturated acylimidazoles.
  
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18. Scheme 17: Stereocontrolled synthesis of 3,5,7-all-syn and anti,anti-stereotriads via iterative Cu ECAs.
  
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19. Scheme 18: Stereocontrolled synthesis of anti,syn- and anti,anti-3,5,7-(Me,OR,Me) units via iterative Cu ECA/B...
  
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20. Scheme 19: Cu-catalyzed ECA of dialkylzinc reagents to α,β-unsaturated N-acyloxazolidinones.
  
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21. Scheme 20: Cu/phosphoramidite L16-catalyzed ECA of dialkylzincs to α,β-unsaturated N-acyl-2-pyrrolidinones.
  
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22. Scheme 21: Cu/(R,S)-Josiphos (L9)-catalyzed ECA of Grignard reagents to α,β-unsaturated amides.
  
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23. Scheme 22: Cu/Josiphos (L9)-catalyzed ECA of Grignard reagents to polyunsaturated amides.
  
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24. Scheme 23: Cu-catalyzed ECA of trimethylaluminium to N-acylpyrrole derivatives.
  
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Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

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Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

Man-Man Wang,
Hao Huang,
Lei Shu,
Jian-Min Liu,
Jian-Qiu Zhang,
Yi-Le Yan and
Da-Yong Zhang

Full Research Paper
Published 19 Feb 2020

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1. Graphical Abstract
2. Scheme 1: The commonly recognized HPPD catalytic reaction mechanism.
  
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3. Figure 1: Chemical structures of the commercial HPPD inhibitors.
  
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4. Figure 2: The design strategy of aryloxyacetic acid derivatives as HPPD inhibitors and simulate the binding m...
  
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5. Scheme 2: Synthetic route of the title compounds I. Reagents and conditions: (a) methyl chloroacetate, K₂CO₃,...
  
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6. Scheme 3: Synthetic route of the title compound III. Reagents and conditions: (a) methyl chloroacetate, K₂CO₃...
  
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7. Scheme 4: Synthetic route of the title compounds II. Reagents and conditions: (a) NaOH, TBAB, H₂O, 100 °C; (b...
  
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8. Figure 3: Crystal structures of I18 and III4.
  
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9. Figure 4: Simulated binding mode of mesotrione (A), compound I12 (B) and compound II4 (C) with AtHPPD. The ke...
  
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10. Figure 5: Sum of inhibition rate of title compounds at 150 g ai/ha. (Abbreviations: AJ, Abutilon juncea; AR, ...
  
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11. Figure 6: Simulated folding mode of mesotrione (yellow sticks) and compound II4 (gray sticks) with AtHPPD. Th...
  
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Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

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Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

Rafia Siddiqui and
Rashid Ali

Review
Published 26 Feb 2020

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1. Graphical Abstract
2. Figure 1: List of photoredox catalysts used for C–H bond functionalizations.
  
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3. Figure 2: List of metal-based photoredox catalysts used in this review article.
  
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4. Figure 3: Jablonski diagram.
  
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5. Figure 4: Photoredox catalysis via reductive or oxidative pathways. D = donor, A = acceptor, S = substrate, P...
  
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6. Figure 5: Schematic representation of the combination of photoredox catalysis and transition metal catalysis.
  
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7. Scheme 1: Weinreb amide C–H olefination.
  
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8. Figure 6: Mechanism for the formation of 21 from 19 using photoredox catalyst 11.
  
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9. Scheme 2: C–H olefination of phenolic ethers.
  
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10. Scheme 3: Decarboxylative acylation of acetanilides.
  
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11. Figure 7: Mechanism for the formation of 30 from acetanilide derivatives.
  
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12. Scheme 4: Synthesis of fluorenone derivatives by intramolecular deoxygenative acylation of biaryl carboxylic ...
  
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13. Figure 8: Mechanism for the photoredox-catalyzed synthesis of fluorenone derivatives.
  
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14. Scheme 5: Synthesis of benzothiazoles via aerobic C–H thiolation.
  
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15. Figure 9: Plausible mechanism for the construction of benzothiazoles from benzothioamides.
  
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16. Scheme 6: Synthesis of benzothiazoles via oxidant-free C–H thiolation.
  
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17. Figure 10: Mechanism involved in the synthesis of benzothiazoles via oxidant-free C–H thiolation.
  
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18. Scheme 7: Synthesis of indoles via C–H cyclization of anilides with alkynes.
  
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19. Scheme 8: Preparation of 3-trifluoromethylcoumarins via C–H cyclization of arylpropiolate esters.
  
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20. Figure 11: Mechanistic pathway for the synthesis of coumarin derivatives via C–H cyclization.
  
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21. Scheme 9: Monobenzoyloxylation without chelation assistance.
  
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22. Figure 12: Plausible mechanism for the formation of 71 from 70.
  
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23. Scheme 10: Aryl-substituted arenes prepared by inorganic photoredox catalysis using 12a.
  
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24. Figure 13: Proposed mechanism for C–H arylations in the presence of 12a and a Pd catalyst.
  
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25. Scheme 11: Arylation of purines via dual photoredox catalysis.
  
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26. Scheme 12: Arylation of substituted arenes with an organic photoredox catalyst.
  
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27. Scheme 13: C–H trifluoromethylation.
  
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28. Figure 14: Proposed mechanism for the trifluoromethylation of 88.
  
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29. Scheme 14: Synthesis of benzo-3,4-coumarin derivatives.
  
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30. Figure 15: Plausible mechanism for the synthesis of substituted coumarins.
  
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31. Scheme 15: Oxidant-free oxidative phosphonylation.
  
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32. Figure 16: Mechanism proposed for the phosphonylation reaction of 100.
  
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33. Scheme 16: Nitration of anilines.
  
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34. Figure 17: Plausible mechanism for the nitration of aniline derivatives via photoredox catalysis.
  
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35. Scheme 17: Synthesis of carbazoles via intramolecular amination.
  
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36. Figure 18: Proposed mechanism for the formation of carbazoles from biaryl derivatives.
  
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37. Scheme 18: Synthesis of substituted phenols using QuCN.
  
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38. Figure 19: Mechanism for the synthesis of phenol derivatives with photoredox catalyst 8.
  
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39. Scheme 19: Synthesis of substituted phenols with DDQ (5).
  
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40. Figure 20: Possible mechanism for the generation of phenols with the aid of photoredox catalyst 5.
  
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41. Scheme 20: Aerobic bromination of arenes using an acridinium-based photocatalyst.
  
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42. Scheme 21: Aerobic bromination of arenes with anthraquinone.
  
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43. Figure 21: Proposed mechanism for the synthesis of monobrominated compounds.
  
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44. Scheme 22: Chlorination of benzene derivatives with Mes-Acr-MeClO₄ (2).
  
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45. Figure 22: Mechanism for the synthesis of 131 from 132.
  
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46. Scheme 23: Chlorination of arenes with 4CzIPN (5a).
  
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47. Figure 23: Plausible mechanism for the oxidative photocatalytic monochlorination using 5a.
  
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48. Scheme 24: Monofluorination using QuCN-ClO₄ (8).
  
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49. Scheme 25: Fluorination with fluorine-18.
  
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50. Scheme 26: Aerobic amination with acridinium catalyst 3a.
  
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51. Figure 24: Plausible mechanism for the aerobic amination using acridinium catalyst 3a.
  
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52. Scheme 27: Aerobic aminations with semiconductor photoredox catalyst 18.
  
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53. Scheme 28: Perfluoroalkylation of arenes.
  
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54. Scheme 29: Synthesis of benzonitriles in the presence of 3a.
  
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55. Figure 25: Plausible mechanism for the synthesis of substituted benzonitrile derivatives in the presence of 3a....
  
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Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

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Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

Yana I. Sakhno,
Maryna V. Murlykina,
Oleksandr I. Zbruyev,
Anton V. Kozyryev,
Svetlana V. Shishkina,
Dmytro Sysoiev,
Vladimir I. Musatov,
Sergey M. Desenko and
Valentyn A. Chebanov

Full Research Paper
Published 27 Feb 2020

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1. Graphical Abstract
2. Scheme 1: Synthesis of tetrahydroazolopyrimidine derivatives.
  
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3. Scheme 2: Various multicomponent reactions involving pyruvic acids (pyruvates) and different α-aminoazoles.
  
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4. Scheme 3: Synthesis of 4-arylamino-substituted tetrahydroquinolines.
  
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5. Scheme 4: Ultrasound-assisted multicomponent reactions of 3-amino-1,2,4-triazole or 5-amino-1H-pyrazole-4-car...
  
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6. Scheme 5: Synthesis of 3-cyano-7-(4-methoxyphenyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid (7)....
  
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7. Scheme 6: Proposed reaction mechanism.
  
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8. Figure 1: Alternative structures A and B for the tetrahydroazolopyrimidines 4.
  
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9. Figure 2: Molecular structure of ethyl 5-(4-bromophenyl)-3-cyano-7-((4-cyano-1H-pyrazol-5-yl)amino)-4,5,6,7-t...
  
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10. Figure 3: Chains of 4g molecules in the crystal phase.
  
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Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

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Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

Ken-ichi Nakashima,
Junko Tomida,
Takao Hirai,
Yoshiaki Kawamura and
Makoto Inoue

Full Research Paper
Published 28 Feb 2020

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1. Graphical Abstract
2. Figure 1: Structures of compounds 1–6.
  
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3. Figure 2: Key HMBC (blue arrows) and COSY (bold bonds) correlations in 1 and 2.
  
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4. Figure 3: a) ORTEP drawing of 1, with thermal ellipsoids indicating 50% probability. The atoms of the minor d...
  
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5. Figure 4: a) ORTEP drawing of 3, with thermal ellipsoids indicating 50% probability. b) Electronic circular d...
  
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6. Figure 5: a) ORTEP drawing of 5, with thermal ellipsoids indicating 50% probability. b) Electronic circular d...
  
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Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

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Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

Amit Raj Sharma,
Enjuro Harunari,
Naoya Oku,
Nobuyasu Matsuura,
Agus Trianto and
Yasuhiro Igarashi

Full Research Paper
Published 02 Mar 2020

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1. Graphical Abstract
2. Figure 1: Structures of (6E,8Z)- and (6E,8E)-5-oxo-6,8-tetradecadienoic acids (1 and 2).
  
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3. Figure 2: COSY and key HMBC correlations for 1 and 2.
  
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4. Figure 3: Spin system simulation for the C8–C9 double bond of 2.
  
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5. Figure 4: Natural keto fatty acids of various origins.
  
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6. Figure 5: PPAR activation by 1 and 2.
  
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Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

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Volume No. 16

2020

Pages 1 - 2362

Table of Contents

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose

Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

Understanding the role of active site residues in CotB2 catalysis using a cluster model

Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

[1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

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

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

Synthesis, liquid crystalline behaviour and structure–property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds

Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

Combination of multicomponent KA² and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

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