Table of Contents
12	Full Research Paper
1	Letter

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Preparation of (2'-deoxy)-5-alkynyluridines 2 and 3, their dicobalt hexacarbonyl derivatives 4 and 5...
  
  Jump to Scheme 1
3. Figure 1: Structures of nucleosides 6 and 7, products of the Nicholas reaction.
  
  Jump to Figure 1
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Modification of lipid A by ArnT.
  
  Jump to Figure 1
3. Scheme 1: Phosphonate and glycal synthesis.
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of methyl phosphonate 11 and octyl phosphonates 16 and 17.
  
  Jump to Scheme 2
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 9–14, doi:10.3762/bjoc.16.2

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Substrates used for the Mizoroki–Heck reaction in this study.
  
  Jump to Figure 1
3. Figure 2: Structures of the identified side products 4 and 5.
  
  Jump to Figure 2
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...
  
  Jump to Scheme 1
5. Scheme 2: Dealkylation of fluorinated analog 23 under the Mizoroki–Heck reaction conditions.
  
  Jump to Scheme 2
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 15–21, doi:10.3762/bjoc.16.3

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Chemical shift data for N-thiobenzoylpiperidine and compound 4a.
  
  Jump to Scheme 1
3. Scheme 2: PPSE promoted ring closure reactions of amido- and thioamido alcohols.
  
  Jump to Scheme 2
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Chemical structures of baicalein (left), cucurbit[8]uril (right).
  
  Jump to Figure 1
3. Figure 2: The possible interaction model for Q[8] and baicalein.
  
  Jump to Figure 2
4. Figure 3: ¹H NMR spectra (400 MHz) of Q[8] (a), baicalein (b) and BALE–Q[8] (1:1) (c) recorded in DCl.
  
  Jump to Figure 3
5. Figure 4: The absorption spectra of BALE upon the addition of Q[8] under different conditions [10 mol·L⁻¹ HCl...
  
  Jump to Figure 4
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...
  
  Jump to Figure 5
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...
  
  Jump to Figure 6
8. Figure 7: The stability curve of UV–vis absorption obtained for an isoconcentration of BALE and the BALE–Q[8]...
  
  Jump to Figure 7
9. Figure 8: The phase solubility graph obtained for BALE in Q[8] at λ = 270 nm.
  
  Jump to Figure 8
10. Figure 9: The clearance rate curve (A) and clearance time curve (B) of ABTS^+· upon increasing the concentrati...
  
  Jump to Figure 9
11. Figure 10: The release curves of BALE and BALE–Q[8].
  
  Jump to Figure 10
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

Full Text

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

PDF
Album
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...
  
  Jump to Figure 1
3. Scheme 1: Synthesis of 4,5-diiodo-1,3-dimesityl-1,2,3-triazolium with iodide, Mes: 2,4,6-Me₃C₆H₂.
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of 4,5-diiodo-1,3-dimesityl-1,2,3-triazolium with different anion.
  
  Jump to Scheme 2
5. Figure 2: Packing structure of 2-I (top), 2-Br (middle) and 2-Cl (bottom). Hydrogen atoms have been omitted f...
  
  Jump to Figure 2
6. Figure 3: Packing structure of 2-BF₄. Hydrogen atoms have been omitted for clarity.
  
  Jump to Figure 3
7. Figure 4: Packing structure of 2-OAc. Hydrogen atoms and solvent molecules have been omitted for clarity.
  
  Jump to Figure 4
8. Figure 5: Packing structure of 2-TFA. Hydrogen atoms and disorder of fluorine atoms have been omitted for cla...
  
  Jump to Figure 5
9. Figure 6: Packing structure of 2-I^.1.5I₂. Hydrogen atoms have been omitted for clarity.
  
  Jump to Figure 6
10. Figure 7: Packing structure of 2-I^.3.5I₂. Hydrogen atoms have been omitted for clarity.
  
  Jump to Figure 7
11. Figure 8: Packing structure of 2-BF₄^.0.5bpy. Hydrogen atoms and dichloromethane have been omitted for clarity....
  
  Jump to Figure 8
12. Figure 9: 1,2,3-Triazole-based halogen model calculation: electrostatic potential surfaces mapped on total de...
  
  Jump to Figure 9
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

Full Text

[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

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

Beilstein J. Org. Chem. 2020, 16, 88–105, doi:10.3762/bjoc.16.11

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escheri...
  
  Jump to Figure 1
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...
  
  Jump to Scheme 1
4. Scheme 2: (a) HClO₄/SiO₂, CH₂Cl₂, −10 °C, 1 h, 76%.
  
  Jump to Scheme 2
5. Scheme 3: (a) NIS, HClO₄/SiO₂, MS 4 Å, CH₂Cl₂, −40 °C, 1 h, 22%.
  
  Jump to Scheme 3
6. Scheme 4: (a) NIS, HClO₄/SiO₂, MS 4 Å, CH₂Cl₂, −45 °C, 1 h, 74%; (b) BnBr, NaOH, TBAB, THF, room temperature,...
  
  Jump to Scheme 4
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 106–110, doi:10.3762/bjoc.16.12

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of styrylquinolizinium derivatives 3a–d.
  
  Jump to Scheme 1
3. Figure 1: Absorption spectra and normalized emission spectrum (Abs. = 0.10, 3b: λ_ex = 394 nm) of derivatives ...
  
  Jump to Figure 1
4. Figure 2: Spectrophotometric titration upon the addition of ct DNA to the styrylquinolizinium derivatives 3a ...
  
  Jump to Figure 2
5. Figure 3: Spectrofluorimetric titration upon the addition of ct DNA to the styrylquinolizinium derivatives 3a...
  
  Jump to Figure 3
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...
  
  Jump to Figure 4
7. Figure 5: Spectrophotometric monitoring of the irradiation of styrylquinolizinium derivatives 3a (A), 3b (B), ...
  
  Jump to Figure 5
8. Figure 6: Absorption of the monomers (c = 20 µM, red) 3b (A) and 3c (B) and their dimers (black) 4b and 4c in...
  
  Jump to Figure 6
9. Figure 7: Photometric monitoring of the photoreaction of 3b (c = 20 µM) to the dimer 4b by irradiation at ca....
  
  Jump to Figure 7
10. Figure 8: ORTEP drawings of cyclobutane derivatives 4b (A) and 4c (B) in the solid state (thermal ellipsoids ...
  
  Jump to Figure 8
11. Scheme 2: Possible pathways for the selective photodimerization of styrylquinolizinium derivatives 3b and 3c.
  
  Jump to Scheme 2
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, ...
  
  Jump to Figure 9
13. Figure 10: A) Photometric and B) CD spectroscopic monitoring of the photoinduced switching (4b: λ_ex = 315 nm, ...
  
  Jump to Figure 10
14. Scheme 3: Photoinduced switching of the DNA binding properties of styrylquinolizinium compound 3b.
  
  Jump to Scheme 3
Supp. Info

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

Full Text

Volume No. 16

2020

Pages 1 - 124

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

Keep Informed