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    1,3-Dipolar cycloaddition reactions of acyl phosphonates with nitrile oxides: synthesis of phosphonate-containing dioxazole derivatives
    (Taylor & Francis Ltd, 2020) Polat-Cakir, Sidika
    New phosphonate-containing five-membered heterocyclic dioxazole derivatives are synthesized via 1,3-dipolar cycloaddition reactions of nitrile oxides used as dipole with acyl phosphonates under basic conditions. Herein, acyl phosphonates take part in the cyclization process as a dipolarophile to afford the related dioxazole compounds in moderate-to-good yields (49-84%). Substituted aryl nitrile oxides and aroyl phosphonates were employed in the 1,3-dipolar cycloaddition reactions where triethylamine was the effective tertiary base. Alkyl version of acyl phosphonate also afforded the expected cycloadduct, that is, dimethyl 5-isopropyl-3-phenyl-1,4,2-dioxazol-5-yl-5-phosphonate. Diethyl/dimethyl 3,5-aryl-1,4,2-dioxazol-5-yl-5-phosphonate derivatives are fully characterized by using H-1 NMR, C-13 NMR, P-31-NMR, and FT along with high-resolution mass spectroscopy.
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    Öğe
    Huisgen Cycloaddition Reaction of Nitrile Imines With Acyl Phosphonates: Synthesis of Phosphonate Containing 1,3,4-Oxadiazoles and DFT Analysis
    (Wiley, 2025) Polat-Cakir, Sidika; Altinisik, Sinem
    The application of the Huisgen cycloaddition reaction between acyl phosphonates (dipolarophile) and highly reactive intermediate nitrile imines (NI) as a 1,3-dipole in situ generated by the conversion of hydrazonyl chlorides in the presence of a base is reported to synthesize the phosphonate-containing 1,3,4-oxadiazole compounds in 53%-89% yields. Oxadiazole compounds stand out as significant target molecules in drug design and development due to their potential biological activities. Having a phosphonate group in the structure of the 1,3,4-oxadiazole may enhance biological activity be enhanced. We have synthesized 10 new phosphonate-containing oxadiazole compounds that are fully characterized by using spectroscopic analysis. Density Functional Theory (DFT) calculations were carried out to compare the energies of the frontier orbitals of the acyl phosphonates (dipolarophile) and NI (1,3 dipole) to determine the nature of the interaction between the dipolarophile and the 1,3-dipole. The relevant Huisgen cycloaddition reaction proceeds via a normal-electron demand (NED) pathway.
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    Recent progress in asymmetric synthesis of aziridine derivatives (microreview)
    (Springer, 2018) Dogan, Ozdemir; Polat-Cakir, Sidika
    This microreview describes recent advances in asymmetric synthesis of aziridine derivatives, which have been published over the last two years.
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    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.