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    Öğe
    A Novel Methodology for the Asymmetric Synthesis of 2,3,5-Trisubstituted Piperazine Derivatives
    (Georg Thieme Verlag Kg, 2024) Beksultanova, Nurzhan; Ozdemir, Ozge; Cakir, Sidika Polat; Aygun, Muhittin; Dogan, Ozdemir
    Piperazines constitute an important structural feature of many pharmaceuticals. For the discovery of new drugs, the ability to modify the lead compound's structure is crucial. Herein, we provide an efficient method for the synthesis of chiral 2,3,5-trisubstituted piperazine structures. Our route enables the synthesis of several novel chiral aryl aziridinyl ketones that could be converted into aziridine-fused bicyclic imines. The reduction of these imines and the nucleophilic ring-opening reaction of the aziridine ring allowed us to synthesize highly functionalized piperazine derivatives.
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    Öğe
    Enantioselective synthesis of 2-aziridinyl phosphonates and studies of their biological activities
    (Amer Chemical Soc, 2016) Dogan, Ozdemir; Cakir, Sidika Polat; Beksultanova, Nurzhan; Altanlar, Nurten; Simsek, Duygu
    [Anstract Not Available]
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    Öğe
    Enantioselective synthesis of new chiral 2-aziridinyl phosphonates and studies of their biological activities
    (Pergamon-Elsevier Science Ltd, 2017) Dogan, Ozdemir; Cakir, Sidika Polat; Beksultanova, Nurzhan; Altanlar, Nurten; Simsek, Duygu; Karabiyik, Hasan
    A new series of chiral aziridinyl phosphonates has been synthesized and evaluated for antibacterial and antifungal activities. For the synthesis, a Gabriel-Cromwell reaction was used to form aziridinyl phosphonates in 52-83% yield. In order to evaluate antibacterial and antifungal activities, MIC values were measured. Although most of the compounds showed insignificant activity, two of them provided low to moderate antifungal activity. (C) 2017 Elsevier Ltd. All rights reserved.
  • Küçük Resim
    Öğe
    FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines
    (Wiley, 2021) Beksultanova, Nurzhan; Gözükara, Zeynep; Araz, Mihrimah; Bulut, Merve; Polat-Çakır, Sıdıka; Aygün, Muhittin; Doğan, Özdemir
    New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl-substituted pyrrolidines by the 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides. 2-Thienyl, 2-furyl, 2-, 3-, and 4-pyridyl aldimines were prepared and used with N-methylmaleimide, dimethyl maleate, tert-butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl-substituted pyrrolidines. 1,3-DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single-crystal X-ray analysis.
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    Öğe
    Synthesis of ?-chloro-?-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates
    (Taylor & Francis Ltd, 2018) Polat-Cakir, Sidika; Beksultanova, Nurzhan; Dogan, Ozdemir
    A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields. [GRAPHICS] .
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    Öğe
    Synthesis of Functionalized Novel ?-Amino-?-alkoxyphosphonates through Regioselective Ring Opening of Aziridine-2-phosphonates
    (Wiley-V C H Verlag Gmbh, 2019) Polat-Cakir, Sidika; Beksultanova, Nurzhan; Dogan, Ozdemir
    Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions provided functionalized alpha-amino-beta-alkoxyphosphonates in 40-91 % yield.