Table of Contents
124	Full Research Paper
17	Review
31	Letter
5	Perspective
1	Commentary
7	Editorial

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

Shou-Mao Shen,
Qing Yang,
Yi Zang,
Jia Li,
Xueting Liu and
Yue-Wei Guo

Full Research Paper
Published 25 Jul 2022

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1. Graphical Abstract
2. Figure 1: Chemical structures of compounds 1–8.
  
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3. Figure 2: ORTEP drawing of 2 (displacement ellipsoids are drawn at the 50% probability level).
  
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4. Figure 3: Experimental and calculated ECD curves of (+)-1.
  
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5. Figure 4: ¹H-¹H COSY, key HMBC correlations, and NOESY correlations of compound 5.
  
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6. Figure 5: Experimental ECD curves of compounds (+)-4, (−)-4 (top), (+)-5, and (−)-5 (bottom).
  
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7. Scheme 1: Proposed cyclization pathway of terpene intermediates and plausible post-modifications of compounds ...
  
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8. Figure 6: Compound 3 reduced the mRNA levels of TNF-α (left) and CCL2 (right) in LPS-stimulated RAW264.7 macr...
  
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Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

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Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

Nisha Devi and
Virender Singh

Full Research Paper
Published 26 Jul 2022

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1. Graphical Abstract
2. Figure 1: Few examples of β-carboline-based drugs and bioactive natural products.
  
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3. Figure 2: 1/3-Formyl-9H-β-carboline: new synthons for the synthesis of β-carboline-fused and substituted fram...
  
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4. Figure 3: A summary of previous reports toward exploration of 3-formyl-9H-β-carbolines.
  
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5. Scheme 1: Synthesis of 3-formyl-9H-pyrido[3,4-b]indole derivatives.
  
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6. Scheme 2: Synthesis of C-3 substituted pyrido[3,4-b]indole MBH derivatives (7 and 8).
  
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7. Scheme 3: Synthesis of C-3 substituted pyrido[3,4-b]indole MBH derivatives 10.
  
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8. Figure 4: Library of C-3-substituted pyrido[3,4-b]indole MBH derivatives 7, 8 and 10.
  
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9. Figure 5: Results of optimization for fluorescence studies: a) contact time; b) concentration; c) solvent.
  
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10. Figure 6: Pictorial representation of structure–fluorescence activity relationship of C-3 substituted pyrido[...
  
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Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

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On Reuben G. Jones synthesis of 2-hydroxypyrazines

Pierre Legrand and
Yves L. Janin

Full Research Paper
Published 29 Jul 2022

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1. Graphical Abstract
2. Scheme 1: Reuben G. Jones synthesis of 2-hydroxypyrazines.
  
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3. Scheme 2: Four hypothetical reaction intermediates.
  
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4. Figure 1: ORTEP depiction of compound 4{1,2}.
  
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5. Scheme 3: Suggested mechanism for the Reuben G. Jones synthesis of 2-hydroxypyrazines.
  
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6. Scheme 4: Tetraethylammonium hydroxide-mediated condensation of glyoxal (1{3}), methylglyoxal (1{4}), or 2-(4...
  
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Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

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Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

Valentin H. K. Fell,
Joseph Cameron,
Alexander L. Kanibolotsky,
Eman J. Hussien and
Peter J. Skabara

Full Research Paper
Published 01 Aug 2022

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1. Graphical Abstract
2. Figure 1: EtH-T-DI-DTT (1).
  
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3. Figure 2: Previously published, ‘bent’ diindenodithienothiophenes [16,24,25].
  
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4. Figure 3: With crystalline films of 2,7-dioctyl[1]benzothieno[3,2-b][1]-benzothiophene (8), obtained by off-c...
  
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5. Figure 4: ITIC, a system with fused thiophenes, in combination with donor polymer 11, also featuring a fused ...
  
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6. Figure 5: The fluorinated derivative of ITIC, IT-4F, achieved, with donor polymer 13, PCEs in OPVs up to 17% [8]....
  
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7. Figure 6: The non-fullerene acceptor Y6 (14) [30], in combination with donor polymer 15, both fused thiophene sys...
  
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8. Figure 7: With a three component system of PBQx-TF, eC9-2Cl, and F-BTA3, a PCE of 19% was achieved [32].
  
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9. Scheme 1: Synthetic route from thiophene to 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dithieno[3,2-b...
  
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10. Scheme 2: Ring closure of key intermediate 27 to achieve 29: a) Methyl 5-bromo-2-iodobenzoate, Aliquat 336®, ...
  
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11. Scheme 3: Synthesis of thiophene derivative 32: a) Magnesium, 2-ethylhexylbromide, spatula tip iodine, anhydr...
  
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12. Scheme 4: Synthesis of the soluble target structure EtH-T-DI-DTT (1): a) 32, Pd(PPh₃)₄, K₂CO₃, THF, H₂O, 70 °...
  
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13. Figure 8: Normalised UV–vis spectra of EtH-T-DI-DTT in 10⁻⁵ M CH₂Cl₂ solution and in the solid state.
  
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14. Figure 9: Cyclic voltammogram for EtH-T-DI-DTT (1), at a scan rate of 0.1 V s⁻¹ using a Pt disk as the workin...
  
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15. Figure 10: The structure of EtH-T-DI-DTT optimised on the B3LYP/6-311g(d,p) level of theory, viewed from the (...
  
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Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

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Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity

Naoki Kise and
Toshihiko Sakurai

Full Research Paper
Published 02 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Electroreductive coupling of phthalic anhydrides with α,β-unsaturated carbonyl compounds and subseq...
  
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3. Scheme 2: Electroreductive coupling of phthalimides with α,β-unsaturated carbonyl compounds and subsequent tr...
  
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4. Scheme 3: Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds and subsequent...
  
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5. Scheme 4: Electroreductive coupling of 1a with 2a and subsequent transformation to 2-cyanonaphthalene-1-ol (3a...
  
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6. Scheme 5: Presumed reaction mechanism of electroreductive coupling of 1 with 2a and subsequent transformation...
  
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7. Scheme 6: Electroreductive coupling of 1a with 2c and subsequent treatment with 1 M HCl.
  
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Beilstein J. Org. Chem. 2022, 18, 956–962, doi:10.3762/bjoc.18.95

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Electrochemical and spectroscopic properties of twisted dibenzo[g,p]chrysene derivatives

Tomoya Imai,
Ryuhei Akasaka,
Naruhiro Yoshida,
Toru Amaya and
Tetsuo Iwasawa

Full Research Paper
Published 03 Aug 2022

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1. Graphical Abstract
2. Figure 1: a) DBC. b) Dependence of E_ox1 on the position of the MeO groups [43]. c) Previous work [52]. d) This work.
  
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3. Figure 2: CVs and SWVs of DBC derivatives in CH₂Cl₂ (≈1.0 × 10⁻³ M, see Supporting Information File 1 for details) including 5.0 × 10⁻² M ...
  
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4. Figure 3: DFT-optimized structures, orbital drawings of HOMO, schematic drawings of orbital interaction, and ...
  
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5. Figure 4: Absorption (solid line) and photoluminescence (dotted red line) spectra (upper graphs) in CH₂Cl₂ an...
  
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Beilstein J. Org. Chem. 2022, 18, 963–971, doi:10.3762/bjoc.18.96

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Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

Shani Zev,
Marion Ringel,
Ronja Driller,
Bernhard Loll,
Thomas Brück and
Dan T. Major

Full Research Paper
Published 04 Aug 2022

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1. Graphical Abstract
2. Figure 1: Summary of yields of HP and IE products in hydropyrene synthase.
  
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3. Scheme 1: Proposed mechanism for HP and IE routes.
  
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4. Figure 2: Free energy profile of hydropyrene cation (a), and IE cation (b) formation in the gas phase. The fr...
  
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5. Figure 3: Structures of intermediates C‘ and C. The distance between the double bond and the cation in interm...
  
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Beilstein J. Org. Chem. 2022, 18, 972–978, doi:10.3762/bjoc.18.97

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

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

Full Research Paper
Published 05 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Electrochemical generation of NHC.
  
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3. Scheme 2: Transformation of electrochemically generated NHC into the corresponding thione by its reaction wit...
  
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4. Scheme 3: Umpolung of the aldehyde carbonyl carbon atom. Formation of the Breslow intermediate using NHCs.
  
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5. Figure 1: Schematic representation of a plane-parallel plate flow electrochemical reactor.
  
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6. Figure 2: C/PVDF anode before (A) and after (B) the first experiment (Table 1, entry 1).
  
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7. Scheme 4: Electrogenerated NHC-catalyzed self-annulation of cinnamaldehyde.
  
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8. Scheme 5: Byproduct obtained from the reaction between methanol and the Breslow intermediate.
  
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9. Figure 3: Expanded view of the electrochemical cell components: (a) Aluminium end plates; (b) insulating PTFE...
  
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Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

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Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

Hui Zheng,
Ying Han,
Jing Sun and
Chao-Guo Yan

Full Research Paper
Published 08 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Representative cycloaddition reactions of phenacylmalononitriles.
  
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3. Figure 1: Single crystal structure of compound 3k.
  
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4. Figure 2: Single crystal structure of compound 4a.
  
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5. Figure 3: Single crystal structure of compound 4c.
  
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6. Scheme 2: Proposed reaction mechanism for compounds 3, 4, and 5.
  
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7. Figure 4: Single crystal structure of compound 5.
  
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8. Scheme 3: Control experiment.
  
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Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

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Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

Dharmendra Das,
Akhil A. Bhosle,
Amrita Chatterjee and
Mainak Banerjee

Full Research Paper
Published 09 Aug 2022

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1. Graphical Abstract
2. Figure 1: Representative examples of important halogen-containing aryl derivatives.
  
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3. Scheme 1: Strategies for halogenation of aromatic compounds using NXS.
  
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4. Scheme 2: General scheme of PEG-400-assisted halogenation of phenols and anilines in an automated grinder usi...
  
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5. Scheme 3: Monohalogenation of phenols and anilines by automated grinding with NXS. All yields refer to the is...
  
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6. Scheme 4: Dihalogenation of phenols and anilines with NXS by automated grinding. All yields refer to the isol...
  
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7. Scheme 5: Gram-scale monobromination of p-cresol by NBS in the automated grinder.
  
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Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

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Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

Yin Chen,
Jinqiu Ren,
Ruimin Yang,
Jie Li,
Sheng-Xiong Huang and
Yijun Yan

Full Research Paper
Published 09 Aug 2022

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1. Graphical Abstract
2. Figure 1: Structures of compounds 1–6, atromentin, and echoside C.
  
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3. Figure 2: (A) Key 2D NMR correlations of compounds 1 and 2. (B) X-ray crystal structure of compounds 1 and 3.
  
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4. Figure 3: (A) The biosynthetic gene cluster of daturamycins. (B) Proposed biosynthetic pathway of daturamycin...
  
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5. Figure 4: (A) HPLC analysis of the fermentation extracts of mutant S. sp. KIB-H1544-∆datA. (B) SDS-PAGE analy...
  
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Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

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New azodyrecins identified by a genome mining-directed reactivity-based screening

Atina Rizkiya Choirunnisa,
Kuga Arima,
Yo Abe,
Noritaka Kagaya,
Kei Kudo,
Hikaru Suenaga,
Junko Hashimoto,
Manabu Fujie,
Noriyuki Satoh,
Kazuo Shin-ya,
Kenichi Matsuda and
Toshiyuki Wakimoto

Full Research Paper
Published 10 Aug 2022

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1. Graphical Abstract
2. Figure 1: Representative natural azoxides.
  
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3. Figure 2: Biosynthetic gene clusters of aliphatic azoxy natural products. Conserved proteins are colored acco...
  
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4. Scheme 1: N₂H₄-detecting colorimetric assay.
  
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5. Figure 3: Structures of azodyrecins (a) and new azodyrecin derivatives, azodyrecins D–G (7–10) (b). Key corre...
  
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6. Figure 4: In vitro characterization of Ady1. Extracted ion chromatograms at m/z 329.3 (black) and m/z 343.3 (...
  
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7. Scheme 2: Proposed biosynthetic pathway of azodyrecin.
  
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8. Figure 5: Sequence similarity network of VlmA-like enzymes in the actinobacterial genomes in the Refseq datab...
  
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Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

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Electrochemical vicinal oxyazidation of α-arylvinyl acetates

Yi-Lun Li,
Zhaojiang Shi,
Tao Shen and
Ke-Yin Ye

Letter
Published 12 Aug 2022

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1. Graphical Abstract
2. Scheme 1: From vinyl acetates to α-azidoketones.
  
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3. Scheme 2: Substrate scope. Reaction conditions: α-arylvinyl acetate (0.5 mmol), TMSN₃ (1.0 mmol), n-Bu₄NPF₆ (...
  
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4. Scheme 3: Derivatization of α-azidoketone 2.
  
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5. Scheme 4: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

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A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH₄/I₂ system

Lin Chen,
Xuan Zhou,
Zhiyong Chen,
Changxu Wang,
Shunjie Wang and
Hanbing Teng

Full Research Paper
Published 17 Aug 2022

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1. Graphical Abstract
2. Scheme 1: The synthesis of formamides and monomethylamines.
  
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3. Scheme 2: The possible reaction mechanism. RDS = rate determining step.
  
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Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

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Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

Hisanori Senboku,
Mizuki Hayama and
Hidetoshi Matsuno

Letter
Published 18 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Generation of N-acyliminium ion: previous and present works.
  
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3. Scheme 2: Electrochemical amidomethylation of indoles 4 in DMA.
  
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4. Scheme 3: Electrochemical amidomethylation of 3-methyl-1H-indole (7) in DMA.
  
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5. Scheme 4: Electrochemical amidomethylation of N-methyl-1H-indole (4a) in DMF.
  
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6. Scheme 5: Probable reaction pathway of the electrochemical amidomethylation.
  
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Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

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Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

Kosuke Takemura,
Kazuki Ohira,
Taiki Higashino,
Keiichi Imato and
Yousuke Ooyama

Full Research Paper
Published 18 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Synthesis of OTK-2 and OTT-2.
  
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3. Figure 1: (a) Photoabsorption and (b) fluorescence (λ_ex = λ_max,abs) spectra of OTK-2 [33] and OTT-2 in toluene. (...
  
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4. Figure 2: Cyclic voltammograms of OTK-2 and OTT-2 (0.1 mM) in DMF containing 0.1 M Bu₄NClO₄ at a scan rate of...
  
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5. Figure 3: (a) HOMO and (b) LUMO of OTK-2 [33] and OTT-2 derived from MO calculations (PM5, INDO/S method). The re...
  
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Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

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Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility

Koichi Mitsudo,
Haruka Inoue,
Yuta Niki,
Eisuke Sato and
Seiji Suga

Full Research Paper
Published 19 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Designed electrochemical hydrogenation of enones 1 with a PEM reactor.
  
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3. Figure 1: Electrochemical setup of the PEM reactor: a) Electrochemical reduction system with the PEM reactor....
  
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4. Figure 2: Reaction profile of the electrochemical hydrogenation of 1a with a PEM reactor using a) Pd/C and b)...
  
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5. Scheme 2: Electrochemical hydrogenation of several enones 1 with a circulating PEM reactor using a Pd/C catho...
  
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6. Scheme 3: Electrochemical hydrogenation of several enones 1 with a circulating PEM reactor using an Ir/C cath...
  
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7. Scheme 4: Mechanistic studies.
  
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8. Scheme 5: Electroreduction of 1a with the circulating PEM reactor using H₂O as a proton source.
  
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Beilstein J. Org. Chem. 2022, 18, 1055–1061, doi:10.3762/bjoc.18.107

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Electrochemical formal homocoupling of sec-alcohols

Kosuke Yamamoto,
Kazuhisa Arita,
Masashi Shiota,
Masami Kuriyama and
Osamu Onomura

Letter
Published 22 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Strategies for the synthesis of vic-1,2-diols.
  
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3. Scheme 2: Substrate scope. Reaction conditions: 1 (1.0 mmol), Et₄NBr (0.1 equiv), imidazole (0.05 equiv), MeC...
  
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4. Scheme 3: Investigation of cross-coupling reaction.
  
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5. Scheme 4: Large-scale experiment.
  
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6. Scheme 5: Control experiments. ^aDetermined by ¹H NMR using 1,3,5-trimethoxybenzene as an internal standard. ^b...
  
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7. Scheme 6: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

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Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

Dmitry Dar’in,
Grigory Kantin,
Alexander Bunev and
Mikhail Krasavin

Letter
Published 22 Aug 2022

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1. Graphical Abstract
2. Figure 1: Diverse bioactive compounds based on the privileged 1,4-DHIQ scaffold.
  
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3. Figure 2: Strategy investigated in this work.
  
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4. Scheme 1: Preparation of 3(2H)-isoquinolones 11. ^aObtained as a 10:1 mixture of regioisomers; purified by cry...
  
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5. Scheme 2: Preparation of 4-diazo-3(2H)-isoquinolones 10. ^aConfirmed by single-crystal X-ray crystallography (...
  
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6. Scheme 3: TfOH-promoted arylation of diazo substrates 10. ^aStructure confirmed by single-crystal X-ray analys...
  
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7. Scheme 4: Unexpected outcome of the TfOH-promoted arylation of 10a with N-formyl-N-methylaniline giving rise ...
  
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8. Scheme 5: Plausible mechanism for the conversion of diazo substrates 10 to 4-aryl products 9 (shown for ArH =...
  
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Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

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Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

Yara Cristina Marchioro Barbosa,
Guilherme Caneppele Paveglio,
Claudio Martin Pereira de Pereira,
Sidnei Moura,
Cristiane Storck Schwalm,
Gleison Antonio Casagrande and
Lucas Pizzuti

Full Research Paper
Published 23 Aug 2022

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1. Graphical Abstract
2. Scheme 1: One-pot approach for the synthesis of 2a. ^aYield calculated vs trichloroethylene by ¹H NMR spectros...
  
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3. Scheme 2: Regioselectivity of the reaction of arylhydrazones 1i and 3i, respectively.
  
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Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

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Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

Laura Holzhauer,
Chloé Liagre,
Olaf Fuhr,
Nicole Jung and
Stefan Bräse

Full Research Paper
Published 24 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Reactions of tetrazoloquinoxalines 1 to 1,2,3-triazoloquinoxalines 3 via CuAAC and denitrogenative ...
  
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3. Scheme 2: Synthesis of tetrazolo[1,5-a]quinoxalines. Reaction conditions: (a) 9, THF or 4 M HCl, 70–110 °C, 2...
  
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4. Scheme 3: Synthesis of 1,2,3-triazole-substituted quinoxalines via CuAAC from tetrazolo[1,5-a]quinoxaline (11a...
  
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5. Scheme 4: Mechanism of CuAAC vs denitrogenative annulation.
  
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6. Scheme 5: Synthesis of bis(tetrazolo)[1,5-a:5',1'-c]quinoxaline (24) and conversion to triazoloimidazoquinoxa...
  
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7. Scheme 6: Synthesis of rhenium tricarbonyl complexes 27a–d and ORTEP diagrams of the resulting molecular stru...
  
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8. Scheme 7: Synthesis of rhenium tricarbonyl complex 29 and ORTEP diagram of the resulting molecular structure ...
  
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9. Scheme 8: Synthesis of a TIQ rhenium complex and ORTEP diagram of the obtained product 30 with the thermal el...
  
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10. Figure 1: UV–vis absorption spectra of the obtained metal complexes (18 µM solutions) in acetonitrile at 20 °...
  
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11. Figure 2: Cyclic voltammetry traces for rhenium complexes 27a–d, 29 and 30: 0.5 mM in MeCN solution with 0.1 ...
  
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Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

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Radical cation Diels–Alder reactions of arylidene cycloalkanes

Kaii Nakayama,
Hidehiro Kamiya and
Yohei Okada

Letter
Published 25 Aug 2022

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1. Graphical Abstract
2. Figure 1: Plausible mechanism of the radical cation Diels–Alder reaction (EDG: electron-donating group).
  
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3. Figure 2: Landscape of the radical cation Diels–Alder reaction.
  
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4. Scheme 1: Radical cation Diels–Alder reaction of β-methylstyrene.
  
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5. Scheme 2: Radical cation Diels–Alder reaction of β-methylanethole (1). Recovered starting material is reporte...
  
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6. Figure 3: Formal expression of radical cations.
  
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7. Scheme 3: Radical cation Diels–Alder reactions of the arylidene cycloalkanes (4–7). Recovered starting materi...
  
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8. Scheme 4: Scope of the radical cation Diels–Alder reaction of arylidene cycloalkanes (recovered starting mate...
  
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Beilstein J. Org. Chem. 2022, 18, 1100–1106, doi:10.3762/bjoc.18.112

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A Streptomyces P450 enzyme dimerizes isoflavones from plants

Run-Zhou Liu,
Shanchong Chen and
Lihan Zhang

Full Research Paper
Published 26 Aug 2022

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1. Graphical Abstract
2. Figure 1: Structures of cattleyaisoflavones A (1), B (2), C (3), and daidzein (4).
  
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3. Figure 2: a) The culture in ISP-2 liquid did not produce 1–3, while feeding with 4 restored the production (a...
  
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4. Figure 3: CYP158C1 dimerizes 4 to form dimers 2 and 5 in vitro (analytical method B, 254 nm). Control conditi...
  
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5. Scheme 1: a) Compatible and b) incompatible substrates of CYP158C1. Products were identified using analytical...
  
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6. Scheme 2: Proposed mechanism of CYP158C1-mediated dimerization of isoflavones.
  
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Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

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Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

Kouichi Matsumoto,
Yuta Hayashi,
Kengo Hamasaki,
Mizuki Matsuse,
Hiyono Suzuki,
Keiji Nishiwaki and
Norihito Kawashita

Letter
Published 29 Aug 2022

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1. Graphical Abstract
2. Scheme 1: Formations of 1,2,3-trialkyl cyclopropanetricarboxylates. Previous reports (reactions 1–3) and this...
  
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3. Scheme 2: Plausible reaction mechanism. EGB = electrogenerated base.
  
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Beilstein J. Org. Chem. 2022, 18, 1116–1122, doi:10.3762/bjoc.18.114

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Heterogeneous metallaphotoredox catalysis in a continuous-flow packed-bed reactor

Wei-Hsin Hsu,
Susanne Reischauer,
Peter H. Seeberger,
Bartholomäus Pieber and
Dario Cambié

Full Research Paper
Published 29 Aug 2022

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1. Graphical Abstract
2. Figure 1: Different approaches to heterogeneous photochemistry in flow. a) Serial micro-batch reactors (SMBR)...
  
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3. Figure 2: Light-mediated carbon–heteroatom cross-couplings. The yields reported are the NMR yields obtained i...
  
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4. Figure 3: Flow diagram of the experimental setup loaded in an injection loop with the reaction mixture.
  
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5. Figure 4: Flow diagram of the experimental setup adopted and time necessary to obtain steady-state conditions...
  
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6. Figure 5: The production campaign of 1 for a seven day experiment.
  
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7. Figure 6: Photo of the packed column with a helical static mixer (polished SS316, 10 cm length, 15 mixing ele...
  
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8. Scheme 1: C–O coupling between 4-iodobenzotrifluoride and N-(Boc)-proline.
  
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Beilstein J. Org. Chem. 2022, 18, 1123–1130, doi:10.3762/bjoc.18.115

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Enzymes in biosynthesis

Jeroen S. Dickschat

Editorial
Published 30 Aug 2022

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1. Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1131–1132, doi:10.3762/bjoc.18.116

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Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

Md Azadur Rahman,
Kana Kuroda,
Hirofumi Endo,
Norihiko Sasaki,
Tomoaki Hamada,
Hiraku Sakai and
Toshiki Nokami

Full Research Paper
Published 30 Aug 2022

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1. Graphical Abstract
2. Figure 1: Structures of chitin and chitosan oligosaccharides.
  
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3. Figure 2: Effect of the anomeric leaving group on the yield of oligosaccharides.
  
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4. Figure 3: Influence of the glycosylation temperature (T2) on the yield of oligosaccharides.
  
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5. Figure 4: Influence of temperatures of anodic oxidation (T1) and glycosylation (T2).
  
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6. Figure 5: MALDI–TOF MS spectra of oligosaccharides.
  
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7. Figure 6: Proposed structures of byproducts of electrochemical polyglycosylation.
  
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8. Figure 7: Proposed mechanisms of electrochemical polyglycosylation.
  
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9. Figure 8: Oxidative potential of monosaccharide 1a, disaccharide 2a, and trisaccharide 3a.
  
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10. Scheme 1: Electrochemical dimerization of tetrasaccharide 4a.
  
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11. Figure 9: Influence of cycle number on the yield of longer oligosaccharides 5a (n = 5)–8a (n = 8). Conditions...
  
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Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

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Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

Nguyen Tran Nguyen,
Vo Viet Dai,
Nguyen Ngoc Tri,
Luc Van Meervelt,
Nguyen Tien Trung and
Wim Dehaen

Full Research Paper
Published 31 Aug 2022

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1. Graphical Abstract
2. Figure 1: Structure of naturally occurring and synthetic 2-pyrrolidone derivatives.
  
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3. Figure 2: Structure of natural compounds containing a 1,5-dihydro-2H-pyrrol-2-one subunit.
  
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4. Scheme 1: Synthesis of substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones 4 via three-component reaction.
  
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5. Scheme 2: Proposed mechanistic path for the synthesis of substituted 4-acetyl-3-hydroxy-3-pyrroline-2-ones.
  
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6. Scheme 3: Tautomerism of compounds 4a–c in DMSO.
  
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7. Figure 3: View of the molecular structure of compound 10aa with atom labeling. Displacement ellipsoids are dr...
  
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8. Figure 4: The PES of reaction for the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-dione 10ab enamine de...
  
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9. Scheme 4: Reaction pathways from 4a, 4a’ to 10ab via IS5 in the gase phase.
  
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10. Scheme 5: Reaction pathways from 4a to 10ab-v2 via IS3 in the gase phase.
  
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11. Figure 5: The PES for the possible pathways (1), (2), (3), and (4) in ethanol solvent.
  
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12. Figure 6: The optimized structures of some reactants, intermediates, transition states, and products in the p...
  
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Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

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Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

Mana Kitano,
Tsuyoshi Saitoh,
Shigeru Nishiyama,
Yasuaki Einaga and
Takashi Yamamoto

Letter
Published 07 Sep 2022

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1. Graphical Abstract
2. Figure 1: (a) Cyclic voltammograms of a BDD electrode in MeCN solution containing cumene (1; 5 mM) and Et₄NClO...
  
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3. Figure 2: Proposed reaction mechanism of electro-conversion of cumene (1) into acetophenone (3).
  
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Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

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Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

Houchao Xu,
Anne Wochele,
Minghe Luo,
Gregor Schnakenburg,
Yuhui Sun,
Heike Brötz-Oesterhelt and
Jeroen S. Dickschat

Letter
Published 07 Sep 2022

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1. Graphical Abstract
2. Scheme 1: Structures of hangtaimycin (1) and its co-metabolites.
  
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3. Scheme 2: First synthetic route towards TDD (4).
  
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4. Figure 1: HPLC analyses of (Z)-4 on a chiral stationary phase. A) Nearly racemic 4 from the first synthetic r...
  
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5. Scheme 3: Second synthetic route towards TDD ((Z)-4).
  
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6. Figure 2: X-ray structure of (rac)-4.
  
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7. Figure 3: Bioactivity testing with hangtaimycin (1). A) Growth retardation of model species B. subtilis 168 a...
  
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Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

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Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

Oleg A. Levitskiy,
Olga I. Aglamazova,
Yuri K. Grishin and
Tatiana V. Magdesieva

Full Research Paper
Published 08 Sep 2022

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1. Graphical Abstract
2. Figure 1: Cyclic voltammograms obtained for complexes 1 (black), 2 (blue), 3 (green), 4 (red) (MeCN, 0.05 M Bu...
  
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3. Scheme 1: Synthesis of complex 4.
  
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4. Figure 2: Key correlations in the NOESY spectrum of complex (S)-4 and the corresponding characteristic fragme...
  
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5. Scheme 2: Reductive three-membered ring-opening and follow-up chemical steps.
  
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6. Figure 3: Correlations in the HMBC spectra of 6a and 6b and spin coupling constants in the ¹H NMR spectrum of ...
  
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7. Scheme 3: Electrochemically induced ring-opening followed by intramolecular cyclization.
  
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8. Scheme 4: One-pot multistep approach to the cysteine derivatives.
  
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9. Figure 4: Characteristic correlations in the NOESY spectra of diastereomeric complexes 10 and the correspondi...
  
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Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

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Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

Ashish Kumar Mazumdar,
Gyana Prakash Nanda,
Nisha Yadav,
Upasana Deori,
Upasha Acharyya,
Bahadur Sk and
Pachaiyappan Rajamalli

Full Research Paper
Published 08 Sep 2022

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1. Graphical Abstract
2. Scheme 1: Synthetic schemes of BPy-pTC and BPy-p3C.
  
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3. Figure 1: (a) Normalized absorption spectra of BPy-pTC and BPy-p3C in toluene at room temperature; (b) normal...
  
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4. Figure 2: Transient photoluminescence decay (λ_ex = 375 nm) of (a) BPy-pTC and (b) BPy-p3C in degassed THF (10...
  
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5. Figure 3: AIEE studies: Emission spectra (λ_ex = 375 nm, 10 µM) of (a) BPy-pTC and (d) BPy-p3C in THF with inc...
  
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6. Figure 4: Normalized fluorescence at room temperature and phosphorescence spectra at 77 K (λ_ex = 375 nm, 10 µ...
  
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7. Figure 5: Transient photoluminescence decay (λ_ex = 375 nm, 20 µM) of (a) BPy-pTC and (b) BPy-p3C aggregates i...
  
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8. Figure 6: Fluorescence switching by acid and base fumes exposure: Emission spectra (λ_ex = 375 nm) of (a) BPy-p...
  
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9. Figure 7: Fluorescence intensity vs number of exposures for (a) BPy-p3C and (b) BPy-pTC thin films upon expos...
  
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Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

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Lewis acid-catalyzed Pudovik reaction–phospha-Brook rearrangement sequence to access phosphoric esters

Jin Yang,
Dang-Wei Qian and
Shang-Dong Yang

Letter
Published 09 Sep 2022

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1. Graphical Abstract
2. Scheme 1: Different strategies for phospha-Brook reactions.
  
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3. Scheme 2: Scope of 1 (secondary phosphine oxides and phosphonate). Reaction conditions: 1 (0.2 mmol), 2-pyrid...
  
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4. Scheme 3: Scope of 2 (α-pyridinealdehydes and α-pyridones). Reaction conditions: diphenylphosphine oxide (1a,...
  
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5. Scheme 4: Control experiments.
  
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6. Scheme 5: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2022, 18, 1188–1194, doi:10.3762/bjoc.18.123

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Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

Péter Kisszékelyi,
Tibor Peňaška,
Klára Stankovianska,
Mária Mečiarová and
Radovan Šebesta

Full Research Paper
Published 09 Sep 2022

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

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Volume No. 18

2022

Pages 1 - 1771

Table of Contents

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

On Reuben G. Jones synthesis of 2-hydroxypyrazines

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity

Electrochemical and spectroscopic properties of twisted dibenzo[g,p]chrysene derivatives

Understanding the competing pathways leading to hydropyrene and isoelisabethatriene

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

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

New azodyrecins identified by a genome mining-directed reactivity-based screening

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH₄/I₂ system

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility

Electrochemical formal homocoupling of sec-alcohols

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

Radical cation Diels–Alder reactions of arylidene cycloalkanes

A Streptomyces P450 enzyme dimerizes isoflavones from plants

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

Heterogeneous metallaphotoredox catalysis in a continuous-flow packed-bed reactor

Enzymes in biosynthesis

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

Lewis acid-catalyzed Pudovik reaction–phospha-Brook rearrangement sequence to access phosphoric esters

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

Other Beilstein-Institut Open Science Activities

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