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5 article(s) from Nikolaev, Valerij A

Novel photochemical reactions of carbocyclic diazodiketones without elimination of nitrogen – a suitable way to N-hydrazonation of C–H-bonds

Liudmila L. Rodina,
Xenia V. Azarova,
Jury J. Medvedev,
Dmitrij V. Semenok and
Valerij A. Nikolaev

Full Research Paper
Published 28 Aug 2018

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1. Graphical Abstract
2. Figure 1: The structures of carbocyclic diazodiketones 1a–g and C–H-donating tetrahydrofuran used in the proj...
  
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3. Figure 2: Molecular structure of hydrazone 2b as determined by X-ray analysis data (Olex2 plot with 50% proba...
  
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4. Scheme 1: Photochemical cycloelimination of furans from hydrazones 2d,e.
  
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5. Scheme 2: Different pathways of diazodiketones 1 light-induced reactions in the singlet (reaction I) and trip...
  
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Beilstein J. Org. Chem. 2018, 14, 2250–2258, doi:10.3762/bjoc.14.200

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Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes

Jury J. Medvedev,
Ilya V. Efimov,
Yuri M. Shafran,
Vitaliy V. Suslonov,
Vasiliy A. Bakulev and
Valerij A. Nikolaev

Full Research Paper
Published 30 Nov 2017

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1. Graphical Abstract
2. Scheme 1: General scheme for intramolecular heterocylization of intermediate X-ylides.
  
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3. Figure 1: Thioamides 1a–e, diazoesters 2a–d and Rh(II)-catalysts used in the project.
  
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4. Figure 2: The structures of compounds 4a and 3b according to the data of X-ray analysis (Olex2 plot with 50% ...
  
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5. Scheme 2: Rh(II)-Catalyzed reactions of α-diazocyanoacetic ester 2d with α-cyanothioacetamides 1a–e.
  
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6. Figure 3: The structure of thiophene 5c according to the data of X-ray analysis (Olex2 plot with 50% probabil...
  
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7. Scheme 3: Interaction of thioacetamide 1e with dirhodium pivalate to produce complex 6e.
  
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8. Figure 4: The structure of the complex 6e according to the data of X-ray analysis (Olex2 plot with 50% probab...
  
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9. Scheme 4: The assumed mechanism for the formation of thiophenes 3, 5.
  
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10. Scheme 5: The plausible mechanism for the formation of thiophenes 4.
  
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Beilstein J. Org. Chem. 2017, 13, 2569–2576, doi:10.3762/bjoc.13.253

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Unusual reactions of diazocarbonyl compounds with α,β-unsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N–H-insertion products

Valerij A. Nikolaev,
Jury J. Medvedev,
Olesia S. Galkina,
Ksenia V. Azarova and
Christoph Schneider

Letter
Published 25 Aug 2016

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1. Graphical Abstract
2. Scheme 1: Catalytic reactions of diazocarbonyl compounds with unsaturated δ-amino esters.
  
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3. Figure 1: The structures of the starting compounds 1–3 and catalysts used in this study.
  
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4. Scheme 2: The assumed pathway for the occurance of amides 6a–c by way of the catalytic Wolff rearrangement.
  
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5. Scheme 3: The assumed mechanism for the formation of the amides 4 and 7 during oxidative cleavage of the N–H-...
  
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Beilstein J. Org. Chem. 2016, 12, 1904–1910, doi:10.3762/bjoc.12.180

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On the strong difference in reactivity of acyclic and cyclic diazodiketones with thioketones: experimental results and quantum-chemical interpretation

Andrey S. Mereshchenko,
Alexey V. Ivanov,
Viktor I. Baranovskii,
Grzegorz Mloston,
Ludmila L. Rodina and
Valerij A. Nikolaev

Full Research Paper
Published 20 Apr 2015

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1. Graphical Abstract
2. Scheme 1: The key experimental results on the DDC 1 reactions with thioketones 2 [19-21].
  
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3. Figure 1: Diazo compounds 1 and thioketones 2 used in the study.
  
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4. Scheme 2: General scheme for reactions of DDC 1 with thiobenzophenone (2a).
  
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5. Figure 2: Optimized structures of the lowest energy Z,E-conformers of diazo compounds 1a–d.
  
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6. Scheme 3: Reactions of the intermediate thiocarbonyl ylide 7'd via competative 1,5-EC (a) or 1,3-EC (b) follo...
  
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Beilstein J. Org. Chem. 2015, 11, 504–513, doi:10.3762/bjoc.11.57

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Less reactive dipoles of diazodicarbonyl compounds in reaction with cycloaliphatic thioketones – First evidence for the 1,3-oxathiole–thiocarbonyl ylide interconversion

Valerij A. Nikolaev,
Alexey V. Ivanov,
Ludmila L. Rodina and
Grzegorz Mlostoń

Full Research Paper
Published 02 Dec 2013

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1. Graphical Abstract
2. Figure 1: Thioketones 1 and diazodicarbonyl compounds 2.
  
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3. Figure 2: ORTEP plot [17] of the molecular structure of the 1,3-oxathiole 3a (50% probability ellipsoids; arbitra...
  
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4. Scheme 1: Reaction of diazocarbonyl compounds 2a,c,e with adamantane-2-thione (1b).
  
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5. Scheme 2: Three possible pathways A, B and C for the formation of 1,3-oxathioles 3,7 and thiiranes 5 and 8 fr...
  
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6. Scheme 3: Two competitive transformations of dibenzoyldiazomethane (2b) at 80 °С leading to 3b and 4b.
  
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7. Scheme 4: Interconversion of 1,3-oxathiole 3e and C=S ylide 6e’ accompanied by 1,3-electrocyclization and des...
  
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8. Figure 3: Energy profile for the transformation of 1,3-oxathiole 3e to alkene 5e. Relative free energies (kca...
  
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Beilstein J. Org. Chem. 2013, 9, 2751–2761, doi:10.3762/bjoc.9.309

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