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6 article(s) from Shishkina, Svetlana V

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

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Published 27 Feb 2020

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

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Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

Maryna V. Murlykina,
Oleksandr V. Kolomiets,
Maryna M. Kornet,
Yana I. Sakhno,
Sergey M. Desenko,
Victoriya V. Dyakonenko,
Svetlana V. Shishkina,
Oleksandr A. Brazhko,
Vladimir I. Musatov,
Alexander V. Tsygankov,
Erik V. Van der Eycken and
Valentyn A. Chebanov

Full Research Paper
Published 12 Jun 2019

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1. Graphical Abstract
2. Scheme 1: An overview of heterocyclic acids used in the Ugi reaction.
  
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3. Scheme 2: Synthesis of pyrazolopyridine carboxylic acids 4 [45] and 7 [45] in Doebner-type reaction.
  
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4. Figure 1: Molecular structure of N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-6-(4-methoxyphenyl)-3-...
  
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Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

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Complexation of molecular clips containing fragments of diphenylglycoluril and benzocrown ethers with paraquat and its derivatives

Leonid S. Kikot',
Catherine Yu. Kulygina,
Alexander Yu. Lyapunov,
Svetlana V. Shishkina,
Roman I. Zubatyuk,
Tatiana Yu. Bogaschenko and
Tatiana I. Kirichenko

Full Research Paper
Published 04 Oct 2017

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1. Graphical Abstract
2. Figure 1: Chemical structures of hosts 1–6 and guests 7–10.
  
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3. Figure 2: HF/6-311+G** calculated 3D molecular electrostatic potential of the guests 7–10. The color code spa...
  
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4. Figure 3: Partial ¹H NMR spectra (300 MHz, CD₃CN/CDCl₃ 4:3, v/v) of (a) free host 3, (b) 3 and 1.0 equiv of 7...
  
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5. Figure 4: The changes observed in the UV–vis spectra during the titration of clip 2 with paraquat (7) in acet...
  
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6. Figure 5: Stability constant dependence for the complexes (lgK) of molecular clips 1–5 with guests 7–10 on th...
  
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7. Figure 6: Molecular structures of complexes of clips 3, 2 and 5 with paraquat (7). Anions and solvate molecul...
  
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8. Figure 7: Crystal packing of molecules in complexes of clips 2, 3 and 5 with paraquat (7). Anions and solvate...
  
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9. Figure 8: Molecular structures of complexes 2@8 and 3@8. The hydrogen bonds are shown by blue lines. Anions a...
  
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10. Figure 9: Molecular structures of complexes 2@9 and 3@9. The hydrogen bonds are represented by blue lines. An...
  
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11. Figure 10: Molecular structures of complexes 2@10 and 3@10. Anions and solvate molecules are omitted for clari...
  
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Beilstein J. Org. Chem. 2017, 13, 2056–2067, doi:10.3762/bjoc.13.203

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New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

Maryna V. Murlykina,
Maryna N. Kornet,
Sergey M. Desenko,
Svetlana V. Shishkina,
Oleg V. Shishkin,
Aleksander A. Brazhko,
Vladimir I. Musatov,
Erik V. Van der Eycken and
Valentin A. Chebanov

Full Research Paper
Published 31 May 2017

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1. Graphical Abstract
2. Scheme 1: Aminoazoles in GBB-3CR and Ugi-4CR.
  
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3. Scheme 2: Reactivity of 5-amino-N-aryl-1H-pyrazole-4-carboxamide and 3-amino-5-methylisoxazole in GBB-3CR and...
  
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4. Figure 1: Alternative structures A and B for compounds 4 and 6.
  
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5. Figure 2: Selected data of HSQC and HMBC experiments for compound 4a.
  
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6. Figure 3: Molecular structure of 3-(tert-butylamino)-2-(4-chlorophenyl)-N-(4-fluorophenyl)-1H-imidazo[1,2-b]p...
  
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7. Figure 4: Selected data of NOE and HSQC experiments for compound 9d.
  
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8. Figure 5: Molecular structure of N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-N-(5-methylisoxazol-3-...
  
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Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

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The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

Volodymyr V. Tkachenko,
Elena A. Muravyova,
Sergey M. Desenko,
Oleg V. Shishkin,
Svetlana V. Shishkina,
Dmytro O. Sysoiev,
Thomas J. J. Müller and
Valentin A. Chebanov

Full Research Paper
Published 17 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Some three-component reactions involving N-aryl-3-oxobutanamides.
  
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3. Scheme 2: Some Biginelli-type three-component condensations with salicylaldehyde.
  
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4. Scheme 3: Three-component heterocyclization of 5-amino-3-methylisoxazole (1), salicylaldehyde (2) and N-(2-me...
  
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5. Figure 1: The possible structure of an intermediate complex in reactions forming the heterocycles 6.
  
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6. Scheme 4: Possible pathways for the three-component reaction of 5-amino-3-methylisoxazole (1), salicylaldehyd...
  
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7. Figure 2: Alternative structures 5a and 5'a for dihydroisoxazolopyridine 5a and selected NOESY correlations.
  
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8. Figure 3: Alternative structures 6a, 6'a and 6''a for compound 6a.
  
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9. Figure 4: Selected data from NOESY experiments and relative stereochemistry of stereogenic centers at positio...
  
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10. Figure 5: Molecular structure of compound 6a according to X-ray diffraction data.
  
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Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

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The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

Tatyana L. Pavlovskaya,
Fedor G. Yaremenko,
Victoria V. Lipson,
Svetlana V. Shishkina,
Oleg V. Shishkin,
Vladimir I. Musatov and
Alexander S. Karpenko

Full Research Paper
Published 09 Jan 2014

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1. Graphical Abstract
2. Figure 1: The NOE correlations of the signals in ¹H NMR spectra of compounds 4b–4d.
  
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3. Figure 2: Molecular structure of spirooxindole 4a according to X-ray diffraction data.
  
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4. Figure 3: The NOE correlations of the signals in ¹H NMR spectrum of compound 6c.
  
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5. Figure 4: Molecular structure of spirooxindole 6a observed in crystal phase as solvate with methanol accordin...
  
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6. Scheme 1: The mechanism of the regioselective synthesis of compounds 4 and 6.
  
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7. Figure 5: Conformations of acrylamide and benzoylacrylic acid.
  
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8. Figure 6: The Fukui function indices of acrylamide, azomethine ylide and benzoylacrylic acid.
  
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9. Scheme 2: The synthesis of compounds 7a–7c.
  
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10. Figure 7: The selected COSY, NOESY and HMBC correlations of the signals in the ¹H and ¹³C NMR spectra of comp...
  
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11. Scheme 3: Tentative reaction mechanism for the decarboxylative cyclative rearrangement of the initial three-c...
  
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Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

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