Table of Contents
45	Full Research Paper
10	Letter
8	Review

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

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

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

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Biologically and medicinally important 3-alkenylindoles.
  
  Jump to Figure 1
3. Scheme 1: a) Previous and b) present work related to the synthesis of 3-alkenylindoles.
  
  Jump to Scheme 1
4. Scheme 2: Substrate scope for the C–H alkenylation of the indoles 1. Reaction conditions: 1 (1 mmol), 2 (2 mm...
  
  Jump to Scheme 2
5. Scheme 3: a) Three-phase test to determine a homogeneous or heterogeneous catalytic mechanism of action for t...
  
  Jump to Scheme 3
6. Scheme 4: Probable catalytic mechanism for the transformation of 1a by the RuNC.
  
  Jump to Scheme 4
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 149–158, doi:10.3762/bjoc.16.17

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of carbamothioates from xanthate esters and benzyl isocyanides.
  
  Jump to Scheme 1
3. Figure 1: Substrate scope for the synthesis of carbamothioates. Reaction conditions for methods A and B: sodi...
  
  Jump to Figure 1
4. Figure 2: ORTEP diagram of O-benzyl (4-fluorobenzyl)carbamothioate (4c).
  
  Jump to Figure 2
5. Figure 3: Rotamers of thionocarbamates 4 (top) and computer-minimized structures of 4c (bottom).
  
  Jump to Figure 3
6. Scheme 2: Proposed general reaction mechanism for the formation of carbamothioates (e.g., 4a) from xanthate e...
  
  Jump to Scheme 2
7. Figure 4: Optimized geometries of the reactants, transition states, intermediates, and products of the propos...
  
  Jump to Figure 4
8. Figure 5: Relative energies of the reactants, transition states (TS1–TS3), and intermediates (Int1–Int3) of t...
  
  Jump to Figure 5
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 159–167, doi:10.3762/bjoc.16.18

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Scope of the propargylation reaction. Reactions were performed with the appropriate aldehyde (1 mmo...
  
  Jump to Scheme 1
3. Scheme 2: Synthesis of potassium allenyltrifluoroborate (4).
  
  Jump to Scheme 2
4. Scheme 3: Propargylation of aldehydes using potassium allenyltrifluoroborate (4).
  
  Jump to Scheme 3
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 175–184, doi:10.3762/bjoc.16.20

Full Text

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

Akihiro Yuasa,
Kazunori Nagao and
Hirohisa Ohmiya

Letter
Published 07 Feb 2020

PDF
Album
1. Graphical Abstract
2. Scheme 1: Our strategy.
  
  Jump to Scheme 1
3. Scheme 2: Allylic cross-coupling using aldehydes as α-alkoxyalkyl anions.
  
  Jump to Scheme 2
4. Scheme 3: Substrate scope and reaction conditions. a) reactions were carried out with 1 (0.4 mmol), 2 (0.2 mm...
  
  Jump to Scheme 3
5. Scheme 4: Stoichiometric reaction.
  
  Jump to Scheme 4
6. Scheme 5: Possible pathway.
  
  Jump to Scheme 5
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 185–189, doi:10.3762/bjoc.16.21

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

Full Text

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

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

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

Full Text

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

Rafia Siddiqui and
Rashid Ali

Review
Published 26 Feb 2020

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

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of tetrahydroazolopyrimidine derivatives.
  
  Jump to Scheme 1
3. Scheme 2: Various multicomponent reactions involving pyruvic acids (pyruvates) and different α-aminoazoles.
  
  Jump to Scheme 2
4. Scheme 3: Synthesis of 4-arylamino-substituted tetrahydroquinolines.
  
  Jump to Scheme 3
5. Scheme 4: Ultrasound-assisted multicomponent reactions of 3-amino-1,2,4-triazole or 5-amino-1H-pyrazole-4-car...
  
  Jump to Scheme 4
6. Scheme 5: Synthesis of 3-cyano-7-(4-methoxyphenyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid (7)....
  
  Jump to Scheme 5
7. Scheme 6: Proposed reaction mechanism.
  
  Jump to Scheme 6
8. Figure 1: Alternative structures A and B for the tetrahydroazolopyrimidines 4.
  
  Jump to Figure 1
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...
  
  Jump to Figure 2
10. Figure 3: Chains of 4g molecules in the crystal phase.
  
  Jump to Figure 3
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of compounds 1–6.
  
  Jump to Figure 1
3. Figure 2: Key HMBC (blue arrows) and COSY (bold bonds) correlations in 1 and 2.
  
  Jump to Figure 2
4. Figure 3: a) ORTEP drawing of 1, with thermal ellipsoids indicating 50% probability. The atoms of the minor d...
  
  Jump to Figure 3
5. Figure 4: a) ORTEP drawing of 3, with thermal ellipsoids indicating 50% probability. b) Electronic circular d...
  
  Jump to Figure 4
6. Figure 5: a) ORTEP drawing of 5, with thermal ellipsoids indicating 50% probability. b) Electronic circular d...
  
  Jump to Figure 5
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of (6E,8Z)- and (6E,8E)-5-oxo-6,8-tetradecadienoic acids (1 and 2).
  
  Jump to Figure 1
3. Figure 2: COSY and key HMBC correlations for 1 and 2.
  
  Jump to Figure 2
4. Figure 3: Spin system simulation for the C8–C9 double bond of 2.
  
  Jump to Figure 3
5. Figure 4: Natural keto fatty acids of various origins.
  
  Jump to Figure 4
6. Figure 5: PPAR activation by 1 and 2.
  
  Jump to Figure 5
Supp. Info

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

Full Text

Volume No. 16

2020

Pages 1 - 669

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

Keep Informed