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5 article(s) from Boyarskaya, Irina A.

Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

Andrey I. Puzanov,
Dmitry S. Ryabukhin,
Anna S. Zalivatskaya,
Dmitriy N. Zakusilo,
Darya S. Mikson,
Irina A. Boyarskaya and
Aleksander V. Vasilyev

Full Research Paper
Published 15 Sep 2021

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1. Graphical Abstract
2. Scheme 1: Synthesis of 5–arylethynyl-3-aryl-1,2,4-oxadiazoles 3a–e.
  
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3. Scheme 2: Plausible reaction mechanism for transformations of 5-acetylenyl-1,2,4-oxadiazoles 3 in Brønsted su...
  
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4. Scheme 3: Quantitative formation of E/Z-vinyl triflates 4a–c from 5-acetylenyl-1,2,4-oxadiazoles 3a–c in TfOH....
  
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5. Scheme 4: Formation of compound 4d from 5-acetylenyl-1,2,4-oxadiazole 3a in H₂SO₄.
  
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6. Scheme 5: Hydroarylation of 5-acetylenyl-1,2,4-oxadiazole 3a–d by arenes in TfOH leading to compounds E/Z-5a–g...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2021, 17, 2417–2424, doi:10.3762/bjoc.17.158

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Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF₃SO₃H. NMR and DFT studies of dicationic electrophilic species

Dmitry S. Ryabukhin,
Alexey N. Turdakov,
Natalia S. Soldatova,
Mikhail O. Kompanets,
Alexander Yu. Ivanov,
Irina A. Boyarskaya and
Aleksander V. Vasilyev

Full Research Paper
Published 19 Aug 2019

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1. Graphical Abstract
2. Figure 1: Examples of some commercially available pharmaceuticals and agrochemicals containing the benzimidaz...
  
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3. Figure 2: Formation of cationic species by protonation of 5-formyl-4-methylimidazole in TfOH and their reacti...
  
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4. Figure 3: Benzimidazoles 1–8 used in this study.
  
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5. Scheme 1: Reaction of 2-acetylbenzimidazole (2) with TfOH and benzene.
  
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6. Scheme 2: Reactions of hydroxymethyl-substituted benzimidazole 7 and 8 with TfOH and benzene.
  
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7. Scheme 3: Reaction mechanism of the formation of compounds 9–11.
  
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8. Scheme 4: Reaction mechanism of the formation of compounds 12.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191

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Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid

Anna S. Zalivatskaya,
Dmitry S. Ryabukhin,
Marina V. Tarasenko,
Alexander Yu. Ivanov,
Irina A. Boyarskaya,
Elena V. Grinenko,
Ludmila V. Osetrova,
Eugeniy R. Kofanov and
Aleksander V. Vasilyev

Full Research Paper
Published 11 May 2017

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1. Graphical Abstract
2. Figure 1: 1,2,4-Oxadiazole-based drugs.
  
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3. Scheme 1: The hydroarylation of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles 1 under superelectrophilic activat...
  
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4. Figure 2: General structure for various biologically active compounds containing three carbon atoms, two aryl...
  
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5. Figure 3: Selected ¹H, ¹³C, ¹⁵N NMR data for cations Ca and Cm generated by protonation of oxadiazoles 1a and ...
  
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6. Figure 4: X-ray crystal structures of compounds 2a (left) (CCDC 1526767) and 2m (right) (CCDC 1526105); ellip...
  
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Beilstein J. Org. Chem. 2017, 13, 883–894, doi:10.3762/bjoc.13.89

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Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

Dmitry S. Ryabukhin,
Dmitry N. Zakusilo,
Mikhail O. Kompanets,
Anton A.Tarakanov,
Irina A. Boyarskaya,
Tatiana O. Artamonova,
Mikhail A. Khohodorkovskiy,
Iosyp O. Opeida and
Aleksander V. Vasilyev

Full Research Paper
Published 05 Oct 2016

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1. Graphical Abstract
2. Figure 1: Formation of 5-HMF from D-glucose or D-fructose followed by oxidation to 2,5-DFF.
  
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3. Scheme 1: Protonation of 5-HMF (1a) and 2,5-DFF (2) leading to cationic species A, B, C, D.
  
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4. Figure 2: X-ray crystal structure of compounds 5a (a), and 5c (b) (ORTEP diagrams, ellipsoid contour of proba...
  
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Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

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Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

Larisa Yu. Gurskaya,
Diana S. Belyanskaya,
Dmitry S. Ryabukhin,
Denis I. Nilov,
Irina A. Boyarskaya and
Aleksander V. Vasilyev

Full Research Paper
Published 11 May 2016

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1. Graphical Abstract
2. Scheme 1: Transformations of 3-aryl-N-(aryl)propiolamides 1 into 4-arylquinolin-2(1H)-ones 3 or 4,4-diaryl-3,...
  
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3. Figure 1: Molecular structure of 2f (ellipsoid contours of probability levels are 50%).
  
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4. Scheme 2: N-Formylation and N-acylation of dihydroquinolinones 2.
  
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5. Scheme 3: Superelectrophilic activation of the N-formyl group of compounds 5 and their reaction with benzene.
  
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6. Figure 2: LUMO of species C1 and D1.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2016, 12, 950–956, doi:10.3762/bjoc.12.93

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