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28 results on '"Biitseva, Angelina V."'

3. Synthesis of Spirocyclic and Fused Isoxazoline Building Blocks

Author

Chalyk, Bohdan A., primary, Izhyk, Vitalii V., additional, Danyleiko, Kyrylo, additional, Sosunovych, Bohdan, additional, Vashchenko, Bohdan V., additional, Zginnyk, Oleksandr, additional, Olshanska, Violetta, additional, Teodorovic, Peter, additional, Biitseva, Angelina V., additional, Volochnyuk, Dmitriy M., additional, and Grygorenko, Oleksandr O, additional

Published
2023
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5. Reductive Recyclization of sp3-Enriched Functionalized Isoxazolines into α-Hydroxy Lactams

Author

Chalyk, Bohdan A., primary, Khutorianskyi, Andrii V., additional, Vashchenko, Bohdan V., additional, Danyleiko, Kyrylo, additional, Grynyova, Anastasiia, additional, Osipova, Anastasiia O., additional, Kozytskiy, Andriy, additional, Syniuchenko, Darya, additional, Tsymbaliuk, Anton, additional, Gavrilenko, Konstantin S., additional, Biitseva, Angelina V., additional, Volochnyuk, Dmitriy M., additional, Komarov, Igor V., additional, and Grygorenko, Oleksandr O., additional

Published
2021
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11. Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes

Author

Chalyk, Bohdan A., primary, Hrebeniuk, Kateryna V., additional, Fil, Yulia V., additional, Gavrilenko, Konstantin S., additional, Rozhenko, Alexander B., additional, Vashchenko, Bohdan V., additional, Borysov, Oleksandr V., additional, Biitseva, Angelina V., additional, Lebed, Pavlo S., additional, Bakanovych, Iulia, additional, Moroz, Yurii S., additional, and Grygorenko, Oleksandr O., additional

Published
2019
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12. Reductive Recyclization of sp3-Enriched Functionalized Isoxazolines into α-Hydroxy Lactams

Author

Chalyk, Bohdan A., Khutorianskyi, Andrii V., Vashchenko, Bohdan V., Danyleiko, Kyrylo, Grynyova, Anastasiia, Osipova, Anastasiia O., Kozytskiy, Andriy, Syniuchenko, Darya, Tsymbaliuk, Anton, Gavrilenko, Konstantin S., Biitseva, Angelina V., Volochnyuk, Dmitriy M., Komarov, Igor V., and Grygorenko, Oleksandr O.

Abstract

An efficient synthesis (up to a 200 g scale) of 3-hydroxypyrrolidin-2-ones bearing alkyl substituents or functional groups at the C-5 position is described. The reaction sequence started from 1,3-dipolar cycloaddition of in situgenerated nitrile oxides with (meth-)acrylates into 3-substituted isoxazoline-5-carboxylates. The catalytic hydrogenolysis of the isoxazoline N–O bond was optimal upon using H2(1 atm) at rt, with the following order of the catalyst activity: Pd–C > Pd(OH)2–C > Pt–C. The reactions with Pt–C were more selective for the synthesis of pyrrolidones, while Pd–C provided the fastest conversion rates. The stirring efficiency had a positive impact on conversion rather than elevated temperatures (up to 40 °C) or pressure (up to 50 atm). The diastereoselectivity was governed mainly by steric factors, with a dr of 1:1 to 3:1 (cis-and trans-isomers could be separated). Higher homologues (isoxazolinylacetates and -propanoates) were suitable for the synthesis of 6- or 7-substituted 4-hydroxypiperidones and 5-hydroxyazepanones, respectively. The proposed methods are tolerant to functional groups, including CF3(but not CHF2or CH2Cl), ester, and most N-Boc-protected amines. The utility of hydroxyl groups in lactams was shown by functional group transformations. Hydrogenolysis of C(5)-functionalized isoxazolines, bearing trimethylsilyl, phosphonate, or sulfone groups, was also studied to demonstrate limitations.

Published
2022
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17. Efficient Preparation Of N ',N '-1H-Isoindole-1,3-Diylidenedicarbohydrazides Via 1,1,3-Trichloro-1H-Isoindole, And Their Characterization

Author

Hordiyenko, Olga V., Rudenko, Igor V., Biitseva, Angelina V., Turov, Aleksandr V., Arrault, Axelle, Brosse, Nicolas, Fabre, Olivier, Jamart-Gregoire, Brigitte, Zubatyuk, Roman I., and Shishkin, Oleg V.

Abstract

N',N ''-isoindole-1,3-diylidenedialkyl(aryl.heteroaryl)carbohydrazides were prepared in good yields via 1,1,3-trichloro-1H-isoindole, which was shown to be a versatile reagent for their synthesis. Tautomeric structure and conformational behaviour of dicarbohydrazides in solid state as well as in solution have been studied by X-ray crystallography, NMR spectroscopy and quantum calculations. The dependence of Z/E amide-type isomerism upon steric effects and solvent polarity is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

Published
2009

19. Remarkably strong polarization of amidine fragment in the crystals of 1-imino-1H-isoindol-3-amine

Author

Shishkin, Oleg V., primary, Konovalova, Irina S., additional, Zubatyuk, Roman I., additional, Palamarchuk, Gennady V., additional, Shishkina, Svitlana V., additional, Biitseva, Angelina V., additional, Rudenko, Igor V., additional, Tkachuk, Volodymyr A., additional, Kornilov, Mikhail Yu., additional, Hordiyenko, Olga V., additional, and Leszczynski, Jerzy, additional

Published
2012
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21. ChemInform Abstract: Efficient Preparation of N′,N′′-1H-Isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-Trichloro-1H-isoindole, and Their Characterization.

Author

Hordiyenko, Olga V., primary, Rudenko, Igor V., additional, Biitseva, Angelina V., additional, Turov, Aleksandr V., additional, Arrault, Axelle, additional, Brosse, Nicolas, additional, Fabre, Olivier, additional, Jamart-Gregoire, Brigitte, additional, Zubatyuk, Roman I., additional, and Shishkin, Oleg V., additional

Published
2009
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22. Efficient preparation of N′,N″-1H-isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-trichloro-1H-isoindole, and their characterization

Author

Hordiyenko, Olga V., primary, Rudenko, Igor V., additional, Biitseva, Angelina V., additional, Turov, Aleksandr V., additional, Arrault, Axelle, additional, Brosse, Nicolas, additional, Fabre, Olivier, additional, Jamart-Grégoire, Brigitte, additional, Zubatyuk, Roman I., additional, and Shishkin, Oleg V., additional

Published
2009
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24. Synthesis of Cyclopropyl- and Cyclobutylpiperidines: Advanced Building Blocks for Drug Discovery.

Author

Vyzira, Ivan I., Iminov, Rustam T., Tverdokhlebov, Anton, Tolmachev, Andrey A., Shcherbatiuk, Andriy V., Mykhailiuk, Pavel K., and Biitseva, Angelina V.

Subjects
PIPERIDINE derivatives, CYCLOPROPYL compounds, ORGANIC synthesis, WITTIG reaction, OLEFINATION reactions
Abstract

A library of cyclopropyl- and cyclobutylpiperidine derivatives were synthesized from commonly available starting materials through Wittig reactions. [ABSTRACT FROM AUTHOR]

Published
2015
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25. Synthesis of 5H-Pyrrolo[3,4-b]pyrazine-Based Peptidomimetics.

Author

Biitseva, Angelina V., Rudenko, Igor V., Hordiyenko, Olga V., Omelchenko, Iryna V., and Arrault, Axelle

Subjects
*PEPTIDOMIMETICS, *AMINO acids, *HETEROCYCLIC compounds, *HYDRAZIDES, *HYDRAZONES, *ORGANIC synthesis
Abstract

A range of 5H-pyrrolo[3,4-b]pyrazine-based peptidomimetics were designed, and their efficient synthesis starting from 5-imino-5H-pyrrolo[3,4-b]pyrazin-7-amine by subsequent interaction with Nprotected amino acid hydrazides and amino acid esters with N,N-carbonyldiimidazole as the coupling agent was elaborated. [ABSTRACT FROM AUTHOR]

Published
2015
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27. 1 H-Isoindole-Based Potential Peptidomimetics.

Author

Biitseva, Angelina V., Rudenko, Igor V., Hordiyenko, Olga V., Jamart-Grégoire, Brigitte, and Arrault, Axelle

Abstract

A variety of 1 H-isoindole-based peptides was designed as potential mimics, and their efficient synthesis starting from 1-imino-1 H-isoindol-3-amine by subsequent interaction with N-Boc-amino acid hydrazides and amino acid ester isocyanates generated in situ, followed by chain elongation using conventional peptide chemistry, was elaborated. [ABSTRACT FROM AUTHOR]

Published
2012
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28. Reductive Recyclization of sp 3 -Enriched Functionalized Isoxazolines into α-Hydroxy Lactams.

Author

Chalyk BA, Khutorianskyi AV, Vashchenko BV, Danyleiko K, Grynyova A, Osipova AO, Kozytskiy A, Syniuchenko D, Tsymbaliuk A, Gavrilenko KS, Biitseva AV, Volochnyuk DM, Komarov IV, and Grygorenko OO

Subjects
Catalysis, Cycloaddition Reaction, Stereoisomerism, Amines, Lactams
Abstract

An efficient synthesis (up to a 200 g scale) of 3-hydroxypyrrolidin-2-ones bearing alkyl substituents or functional groups at the C-5 position is described. The reaction sequence started from 1,3-dipolar cycloaddition of in situ generated nitrile oxides with (meth-)acrylates into 3-substituted isoxazoline-5-carboxylates. The catalytic hydrogenolysis of the isoxazoline N-O bond was optimal upon using H 2 (1 atm) at rt, with the following order of the catalyst activity: Pd-C > Pd(OH) 2 -C > Pt-C. The reactions with Pt-C were more selective for the synthesis of pyrrolidones, while Pd-C provided the fastest conversion rates. The stirring efficiency had a positive impact on conversion rather than elevated temperatures (up to 40 °C) or pressure (up to 50 atm). The diastereoselectivity was governed mainly by steric factors, with a dr of 1:1 to 3:1 ( cis- and trans -isomers could be separated). Higher homologues (isoxazolinylacetates and -propanoates) were suitable for the synthesis of 6- or 7-substituted 4-hydroxypiperidones and 5-hydroxyazepanones, respectively. The proposed methods are tolerant to functional groups, including CF 3 (but not CHF 2 or CH 2 Cl), ester, and most N -Boc-protected amines. The utility of hydroxyl groups in lactams was shown by functional group transformations. Hydrogenolysis of C(5)-functionalized isoxazolines, bearing trimethylsilyl, phosphonate, or sulfone groups, was also studied to demonstrate limitations.

Published
2022
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