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6 article(s) from Desenko, Sergey M

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

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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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In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

Irina G. Tkachenko,
Sergey A. Komykhov,
Vladimir I. Musatov,
Svitlana V. Shishkina,
Viktoriya V. Dyakonenko,
Vladimir N. Shvets,
Mikhail V. Diachkov,
Valentyn A. Chebanov and
Sergey M. Desenko

Full Research Paper
Published 08 Oct 2019

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1. Graphical Abstract
2. Scheme 1: Three synthetic approaches to dihydrotetrazolo[1,5-a]pyrimidines.
  
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3. Scheme 2: Three-component reaction of 1, 7a,b and 8a–d in water.
  
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4. Figure 1: Molecular structure of 9a according to X-ray data. Displacement ellipsoids are shown at the 50% pro...
  
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5. Scheme 3: Three-component reaction of 5-aminotetrazole (1) with formaldehyde (7a) and acetylacetone (10).
  
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6. Scheme 4: a) Three-component reaction of 5-aminotetrazole (1) with acetaldehyde (7b) and ethyl 4,4,4-trifluor...
  
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Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

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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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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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Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

Eugene S. Gladkov,
Katerina A. Gura,
Svetlana M. Sirko,
Sergey M. Desenko,
Ulrich Groth and
Valentin A. Chebanov

Full Research Paper
Published 30 Nov 2012

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1. Graphical Abstract
2. Figure 1: Some MCRs of aminoazoles with controlled switching of the direction.
  
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3. Figure 2: Some possible products of MCRs involving 4-amino-5-carboxamido-1,2,3-triazole and carbonyl compound...
  
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4. Scheme 1: Multicomponent and sequential reactions of 4-amino-5-carboxamido-1,2,3-triazole with cyclic ketones....
  
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5. Scheme 2: Multicomponent and sequential reactions of 4-amino-5-carboxamido-1,2,3-triazole with aldehydes and ...
  
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Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236

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