Sergey Ryabukhin - Academia.edu (original) (raw)
Papers by Sergey Ryabukhin
Journal of Organic and Pharmaceutical Chemistry, 2014
В огляді вперше систематизовані та узагальнені методи синтезу різноманітних заміщених конденсован... more В огляді вперше систематизовані та узагальнені методи синтезу різноманітних заміщених конденсованих похідних піримідину з використанням NCNCC+C підходу. Розглянуті методи, що базуються на реакції карбонільних сполук з NCNCC бінуклеофілами, зокрема, N-арил(тіо)сечовинами, похідними аніліну та ароматичних гетероциклічних амінів, N-ариламідинами та N-імідоїлфосфо ранами. Хоча ця група методів відома відносно давно, значна кількість сучасних робіт у цьому напрямку присвячена розробці м'яких умов проведення реакції, зокрема з використанням триметилхлоросилану або при дії мікрохвильового випромінення. Окремо обговорені Pd-каталізовані циклізації, у яких як NCNCC компоненти виступають N-ариламідини та N-арилкарбодііміди, а як С-складова-карбон(ІІ) оксид або ізонітрили. Ці методи особливо інтенсивно розвиваються в останні роки і найчастіше є трикомпонентними реакціями, в яких додатково бере участь нуклеофільний реагент; отже, такі процеси мають ряд переваг з точки зору різномаїття сполук, які можуть бути одержані. Розглянуті також інші методи, зокрема реакції кетімінів на основі аміногетероциклів з ізоціанатами, реакції N-арилкарбодіімідів з карбонілом молібдену, Cu-та Rh-каталізовані процеси тощо. Показано, що [5+1]-циклізація дає можливість одержання різних функціоналізованих конденсованих піримідинів, які, окрім бензенового ядра, можуть містити анельовані ядра ізохіноліну, тіазолу, піридину, піразину, триазолу, піразолу тощо.
ACS Omega, 2019
Synthetic approaches toward multigram preparation of spirocyclic α,α-disubstituted pyrrolidines f... more Synthetic approaches toward multigram preparation of spirocyclic α,α-disubstituted pyrrolidines from readily available starting materials are discussed. It was shown that although a number of synthetic methodologies have been known to date, many of the title compounds remain hardly accessible. The most appropriate literature method (which relied on reaction of imines and allyl magnesium halide, followed by bromocyclization) was identified and optimized. It was found that the method is most fruitful for simple non-functionalized substrates. Two novel approaches based on the Sakurai or Petasis reactions of cyclic ketones, followed by hydroboration− oxidation at the allyl moiety thus introduced, were elaborated. The latter method had the largest scope and was beneficial for the substrates containing organosulfur or protected amino functions. For the synthesis of 4-azaspiro[2.4]heptane, an alternative synthetic scheme commencing from tert-butyl cyclopropanecarboxylate (instead of the corresponding ketone) was developed. It was shown that the whole set of the methodologies developed can be used for the synthesis of various spirocyclic α,αdisubstituted pyrrolidinesadvanced building blocks of potential importance to medicinal and agrochemistryat up to a 100 g scale.
Synthesis, 2018
An approach for the multigram synthesis of 3,3-difluorocyclobutyl-substituted building blocks (in... more An approach for the multigram synthesis of 3,3-difluorocyclobutyl-substituted building blocks (including carboxylic acid, amines, alcohols, azide, trifluoroborate ketone) is described. It is shown that, in most cases, ethyl 3,3-difluorocyclobutanecarboxylate is a convenient common synthetic intermediate to obtain the target derivatives. For preparation of 3,3-difluorocyclobutanol or -cyclobutanone, an alternative pathway via reaction of dichloroketene and tert-butyl or benzyl vinyl ether should be applied.
SynOpen, 2017
An approach to isomeric 1,1-disubstituted pyrazolylcyclopropanes that relies on lithium diisoprop... more An approach to isomeric 1,1-disubstituted pyrazolylcyclopropanes that relies on lithium diisopropylamide (LDA) mediated bis-alkylation of the corresponding pyrazolylacetonitriles is developed. The building blocks obtained can be considered as lead-like bioisosteres of arylpyrazole and pyrazolecarboxamide moieties and are thus useful for early drug discovery projects.
ChemInform, 2007
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
ChemInform, 2011
ABSTRACT Organosilane-promoted treatment of anilines of type (I) and (IV) with α-haloketones allo... more ABSTRACT Organosilane-promoted treatment of anilines of type (I) and (IV) with α-haloketones allows access to a wide range of 3-fluoro-, 3-chloro-, and 3-bromoquinolines of synthetic and biological interest.
ACS combinatorial science, Jan 10, 2012
A convenient procedure for the parallel synthesis of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones throu... more A convenient procedure for the parallel synthesis of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones through a three-component condensation of active methylene compounds, aldehydes, and amines was developed. It was shown that the use of acetic acid as the reaction medium was suitable for the considerably reactive substrates with no additional functionalities. The substrates with low reactivity and those possessing carboxylic groups or additional basic centers required the use of DMF as the solvent and chlorotrimethylsilane as the reaction promoter was necessary. More than 3000 pyrrolones were synthesized by the developed procedure. To demonstrate the scope of the described approach 114 library representatives were fully characterized.
Synlett, 2014
The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is... more The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp 3 –sp 3 retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp 3 -rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.
Tetrahedron Letters, 2014
Tetrahedron Letters, 2010
Tetrahedron, 2008
A facile and versatile procedure for the synthesis of 5-hetaryl-3-(2-hydroxybenzoyl)-1H-pyrroles ... more A facile and versatile procedure for the synthesis of 5-hetaryl-3-(2-hydroxybenzoyl)-1H-pyrroles and 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylic acid derivatives was established on the basis of TMSCl promoted recyclization of 3-formylchromone with various hetarylmethylamines and glycine derivatives.
Tetrahedron, 2012
ABSTRACT Figure optionsView in workspace
Synthetic Communications, 2008
... DOI: 10.1080/00397910802044272 Sergey V. Ryabukhin a b * , Andrey S. Plaskon a b , Dmitriy M.... more ... DOI: 10.1080/00397910802044272 Sergey V. Ryabukhin a b * , Andrey S. Plaskon a b , Dmitriy M. Volochnyuk a c , Sergey E. Pipko a & Andrey A. Tolmachev b pages 3032-3043. ... [ 5 5. (a) Tverdokhlebov , AV ; Gorulya , AP ; Tolmachev , AA ; Kostyuk , AN ; Chernega , AN ...
Synthesis, 2007
Aromatic and heteroaromatic dialkylaminoaldehydes react with various active methylene compounds i... more Aromatic and heteroaromatic dialkylaminoaldehydes react with various active methylene compounds in the presence of Me 3 SiCl to give functionally and structurally diverse pyrrolo[1,2a]quinolines, pyrido[1,2-a]quinolines, pyrazolo[3,4-e]indolizines, pyrazolo[4,3-c]quinolizines, benzo[g]pyrrolo[1,2-a]-1,8-naphthyridines, and benzo[g]pyrido[1,2-a]-1,8-naphthyridines in high yield and excellent purity.
Synthesis, 2007
... Alexey S. Degtyarenko a , Andrey A. Tolmachev b , Yulian M. Volovenko a , Anton V. Tverdokhle... more ... Alexey S. Degtyarenko a , Andrey A. Tolmachev b , Yulian M. Volovenko a , Anton V. Tverdokhlebov* b. a Kiev National Taras Shevchenko University, Volodimirska Street 62, 01033 Kiev, Ukraine b Enamine Ltd., Alexandra Matrosova Street 23, 01103 Kiev, Ukraine Fax: +380( ...
![Research paper thumbnail of A New One-Step Route for the Synthesis of Fused Pyrido[1,2- a ]pyrimidin-4-ones](https://attachments.academia-assets.com/94558420/thumbnails/1.jpg)
](Synthesis, 2008
The cyclization of 3-formylchromone with a variety of 2methylpyrimidin-4(3H)-ones promoted by chl... more The cyclization of 3-formylchromone with a variety of 2methylpyrimidin-4(3H)-ones promoted by chlorotrimethylsilane was investigated. A simple and flexible general procedure for the synthesis of a series of fused pyrido[1,2-a]pyrimidin-4-ones is proposed. A set of functionally and structurally diverse pyrido[1,2a]pyrimidin-4-ones were obtained in high yields.
Synlett, 2008
N-Carbamoylamino acids were obtained through the alkylation of monosubstituted parabanic acids fo... more N-Carbamoylamino acids were obtained through the alkylation of monosubstituted parabanic acids followed by hydrolysis of the intermediate products. This new methodology furnishes structurally and functionally diverse N-carbamoylamino acids in high preparative yields and excellent purity.
The Journal of Organic Chemistry, 2007
Journal of Organic and Pharmaceutical Chemistry, 2014
В огляді вперше систематизовані та узагальнені методи синтезу різноманітних заміщених конденсован... more В огляді вперше систематизовані та узагальнені методи синтезу різноманітних заміщених конденсованих похідних піримідину з використанням NCNCC+C підходу. Розглянуті методи, що базуються на реакції карбонільних сполук з NCNCC бінуклеофілами, зокрема, N-арил(тіо)сечовинами, похідними аніліну та ароматичних гетероциклічних амінів, N-ариламідинами та N-імідоїлфосфо ранами. Хоча ця група методів відома відносно давно, значна кількість сучасних робіт у цьому напрямку присвячена розробці м'яких умов проведення реакції, зокрема з використанням триметилхлоросилану або при дії мікрохвильового випромінення. Окремо обговорені Pd-каталізовані циклізації, у яких як NCNCC компоненти виступають N-ариламідини та N-арилкарбодііміди, а як С-складова-карбон(ІІ) оксид або ізонітрили. Ці методи особливо інтенсивно розвиваються в останні роки і найчастіше є трикомпонентними реакціями, в яких додатково бере участь нуклеофільний реагент; отже, такі процеси мають ряд переваг з точки зору різномаїття сполук, які можуть бути одержані. Розглянуті також інші методи, зокрема реакції кетімінів на основі аміногетероциклів з ізоціанатами, реакції N-арилкарбодіімідів з карбонілом молібдену, Cu-та Rh-каталізовані процеси тощо. Показано, що [5+1]-циклізація дає можливість одержання різних функціоналізованих конденсованих піримідинів, які, окрім бензенового ядра, можуть містити анельовані ядра ізохіноліну, тіазолу, піридину, піразину, триазолу, піразолу тощо.
ACS Omega, 2019
Synthetic approaches toward multigram preparation of spirocyclic α,α-disubstituted pyrrolidines f... more Synthetic approaches toward multigram preparation of spirocyclic α,α-disubstituted pyrrolidines from readily available starting materials are discussed. It was shown that although a number of synthetic methodologies have been known to date, many of the title compounds remain hardly accessible. The most appropriate literature method (which relied on reaction of imines and allyl magnesium halide, followed by bromocyclization) was identified and optimized. It was found that the method is most fruitful for simple non-functionalized substrates. Two novel approaches based on the Sakurai or Petasis reactions of cyclic ketones, followed by hydroboration− oxidation at the allyl moiety thus introduced, were elaborated. The latter method had the largest scope and was beneficial for the substrates containing organosulfur or protected amino functions. For the synthesis of 4-azaspiro[2.4]heptane, an alternative synthetic scheme commencing from tert-butyl cyclopropanecarboxylate (instead of the corresponding ketone) was developed. It was shown that the whole set of the methodologies developed can be used for the synthesis of various spirocyclic α,αdisubstituted pyrrolidinesadvanced building blocks of potential importance to medicinal and agrochemistryat up to a 100 g scale.
Synthesis, 2018
An approach for the multigram synthesis of 3,3-difluorocyclobutyl-substituted building blocks (in... more An approach for the multigram synthesis of 3,3-difluorocyclobutyl-substituted building blocks (including carboxylic acid, amines, alcohols, azide, trifluoroborate ketone) is described. It is shown that, in most cases, ethyl 3,3-difluorocyclobutanecarboxylate is a convenient common synthetic intermediate to obtain the target derivatives. For preparation of 3,3-difluorocyclobutanol or -cyclobutanone, an alternative pathway via reaction of dichloroketene and tert-butyl or benzyl vinyl ether should be applied.
SynOpen, 2017
An approach to isomeric 1,1-disubstituted pyrazolylcyclopropanes that relies on lithium diisoprop... more An approach to isomeric 1,1-disubstituted pyrazolylcyclopropanes that relies on lithium diisopropylamide (LDA) mediated bis-alkylation of the corresponding pyrazolylacetonitriles is developed. The building blocks obtained can be considered as lead-like bioisosteres of arylpyrazole and pyrazolecarboxamide moieties and are thus useful for early drug discovery projects.
ChemInform, 2007
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
ChemInform, 2011
ABSTRACT Organosilane-promoted treatment of anilines of type (I) and (IV) with α-haloketones allo... more ABSTRACT Organosilane-promoted treatment of anilines of type (I) and (IV) with α-haloketones allows access to a wide range of 3-fluoro-, 3-chloro-, and 3-bromoquinolines of synthetic and biological interest.
ACS combinatorial science, Jan 10, 2012
A convenient procedure for the parallel synthesis of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones throu... more A convenient procedure for the parallel synthesis of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones through a three-component condensation of active methylene compounds, aldehydes, and amines was developed. It was shown that the use of acetic acid as the reaction medium was suitable for the considerably reactive substrates with no additional functionalities. The substrates with low reactivity and those possessing carboxylic groups or additional basic centers required the use of DMF as the solvent and chlorotrimethylsilane as the reaction promoter was necessary. More than 3000 pyrrolones were synthesized by the developed procedure. To demonstrate the scope of the described approach 114 library representatives were fully characterized.
Synlett, 2014
The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is... more The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp 3 –sp 3 retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp 3 -rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.
Tetrahedron Letters, 2014
Tetrahedron Letters, 2010
Tetrahedron, 2008
A facile and versatile procedure for the synthesis of 5-hetaryl-3-(2-hydroxybenzoyl)-1H-pyrroles ... more A facile and versatile procedure for the synthesis of 5-hetaryl-3-(2-hydroxybenzoyl)-1H-pyrroles and 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylic acid derivatives was established on the basis of TMSCl promoted recyclization of 3-formylchromone with various hetarylmethylamines and glycine derivatives.
Tetrahedron, 2012
ABSTRACT Figure optionsView in workspace
Synthetic Communications, 2008
... DOI: 10.1080/00397910802044272 Sergey V. Ryabukhin a b * , Andrey S. Plaskon a b , Dmitriy M.... more ... DOI: 10.1080/00397910802044272 Sergey V. Ryabukhin a b * , Andrey S. Plaskon a b , Dmitriy M. Volochnyuk a c , Sergey E. Pipko a & Andrey A. Tolmachev b pages 3032-3043. ... [ 5 5. (a) Tverdokhlebov , AV ; Gorulya , AP ; Tolmachev , AA ; Kostyuk , AN ; Chernega , AN ...
Synthesis, 2007
Aromatic and heteroaromatic dialkylaminoaldehydes react with various active methylene compounds i... more Aromatic and heteroaromatic dialkylaminoaldehydes react with various active methylene compounds in the presence of Me 3 SiCl to give functionally and structurally diverse pyrrolo[1,2a]quinolines, pyrido[1,2-a]quinolines, pyrazolo[3,4-e]indolizines, pyrazolo[4,3-c]quinolizines, benzo[g]pyrrolo[1,2-a]-1,8-naphthyridines, and benzo[g]pyrido[1,2-a]-1,8-naphthyridines in high yield and excellent purity.
Synthesis, 2007
... Alexey S. Degtyarenko a , Andrey A. Tolmachev b , Yulian M. Volovenko a , Anton V. Tverdokhle... more ... Alexey S. Degtyarenko a , Andrey A. Tolmachev b , Yulian M. Volovenko a , Anton V. Tverdokhlebov* b. a Kiev National Taras Shevchenko University, Volodimirska Street 62, 01033 Kiev, Ukraine b Enamine Ltd., Alexandra Matrosova Street 23, 01103 Kiev, Ukraine Fax: +380( ...
Synthesis, 2008
The cyclization of 3-formylchromone with a variety of 2methylpyrimidin-4(3H)-ones promoted by chl... more The cyclization of 3-formylchromone with a variety of 2methylpyrimidin-4(3H)-ones promoted by chlorotrimethylsilane was investigated. A simple and flexible general procedure for the synthesis of a series of fused pyrido[1,2-a]pyrimidin-4-ones is proposed. A set of functionally and structurally diverse pyrido[1,2a]pyrimidin-4-ones were obtained in high yields.
Synlett, 2008
N-Carbamoylamino acids were obtained through the alkylation of monosubstituted parabanic acids fo... more N-Carbamoylamino acids were obtained through the alkylation of monosubstituted parabanic acids followed by hydrolysis of the intermediate products. This new methodology furnishes structurally and functionally diverse N-carbamoylamino acids in high preparative yields and excellent purity.
The Journal of Organic Chemistry, 2007