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Öğe A Mild Deoximation of Oximes Catalyzed by Lithium Sulfate(Taylor & Francis Inc, 2024) Uludag, NesimiThe availability of efficient processes to obtain carbonyl compounds is of great interest in preparative organic chemistry.Citation(1) One source of carbonyl compounds is deoximation, and the success of this process has significance for industrial applications,Citation(2-4) as well as the synthesis laboratory.Citation(5-8) Several reagents have been utilized for this purpose with varying degrees of effectiveness.Citation(9-16) As a result of efforts in this area, a number of innovative materials have been produced for the implementation of viable deoximations,Citation(17-22) within the context of catalyst development.Citation(23)(,)Citation(24) In the present work, we focused on the practical aspects of the deoximation of aromatic, aliphatic and heterocyclic ketoximes (Scheme 1). Our starting materials were the appropriate oximes, prepared according to standard literature methods.Citation(25-27) With anhydrous lithium sulfate in chloroform at reflux temperature under nitrogen, we observed formation of the respective ketones in generally good yields (up to 91%, mean 77%, see Table 1, Entry 3) over short reaction times as determined by thin layer chromatography (15-120 min). The method was reliable and tolerated several substrate types. There did not appear to be major substituent effects on reaction times and yields. In conclusion, we have explored a novel deoximation reaction method for the effective conversion of ketoximes to the corresponding ketones using lithium sulfate. Further investigations of the deoximation method are ongoing in our laboratory.Öğe A new and effective method to synthesize carbazolones by rhodium (I)-catalyzed annulation of 2-aminobenzaldehyde with cyclohexane-1,3-diones(Natl Inst Science Communication & Policy Research-Niscpr, 2024) Uludag, NesimiIn this research, substituted carbazolones have been synthesized by treating 2-aminobenzaldehyde and cyclohexane-1,3diones using chlorobis(cyclooctene)rhodium(I)-catalyzed [Rh(coe)2Cl]2 in one-pot reactions and are found to have applications in organic synthesis and the pharmaceutical industry. The reaction proceeds smoothly under mild conditions, affording a range of carbazolone derivatives, and the product isolated in good to excellent yields (up to 93%).Öğe A novel series of tetrahydrothieno[2,3-c]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies(Royal Soc Chemistry, 2023) Serdaroglu, Goncaguel; Uludag, Nesimi; Ustun, Elvan; Colak, NakiIn this study, a series of substituted tetrahydrothieno[2,3-c]pyridin-2-yl (THTP) derivatives, i.e., C1-C3 and N1-N3, was synthesized in one step using 2-amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carbonitrile with two different adjacent chloro- and nitro-substituted groups. Specifically, with a nitrile group on the thiophene structure, six new THTP (C1-C3 and N1-N3)-bearing electron-donating-electron-withdrawing moieties were designed with various pharmacological properties. For the first time in the literature, the synthesis of these target pharmaceutical products was carried out in less steps with high efficiency. Specifically, the notable features of this protocol are its simplicity and high reaction yields. Furthermore, spectroscopic methods were used to verify the structures of all the synthesized compounds (FT-IR, UV, H-1 NMR, and C-13 NMR). Additionally, the binding properties of the molecules with serum albumin were analyzed as a function of concentration and temperature and in the presence of Mg2+, Zn2+, and Ca2+. Moreover, molecular docking calculations were performed against bovine serum albumin, human leukemia inhibitory factor, and DNA. Also, DFT and TD-DFT computational studies were performed at the B3LYP/6-311G** level for structural and spectroscopic confirmation of compounds C1-C3 and N1-N3, and their possible reactivity features were evaluated via FMO frontier molecular orbital and NBO natural bond orbital analyses. Further, their physicochemical properties such as lipophilicity and water solubility, in addition to ADMET properties were estimated and evaluated. Considering the results obtained from the experiments and computations, it is hoped that this work will be a useful guide for future research on drug design.Öğe Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis(Wiley-V C H Verlag Gmbh, 2024) Serdaroglu, Goncaguel; Uludag, Nesimi; Uestuen, ElvanThe construction of pyrroles is an important heterocyclic group comprising many compounds with interesting properties that have led to numerous applications in various fields. We delineate a new synthetic method for the rapid construction of tree-substituted pyrroles from readily available ketoximes as starting materials and also a new mechanism and method has been proposed. It is presented that substituted pyrroles were efficiently synthesized in high yields (up to 81 % yield) through the cyclization reaction of starting ketoximes mediated by 2,3-dichlor-5,6-dicyanobenzoquinone (DDQ). Utilizing this protocol various pyrrole derivatives were synthesized from diethyl acetylene dicarboxylate (DEAD). We then developed the dehydrogenation reaction mechanism of this formation, also studied in detail, also all synthesized compounds were analyzed in detail by spectroscopic techniques (FT-IR, 1H NMR, 13CNMR) which were compared with the computational data estimated at B3LYP/6-311G** level. The thermochemical and electronic properties of the pyrroles were evaluated after optimizing and then confirming the equilibrium structures. ADMT scores were also considered to estimate/elucidate the possible bioavailability tendencies as well as the toxicity. In addition, the interactions of the optimized molecules were evaluated by molecular docking methods against BSA Bovine Serum Albumin and LIF Leukemia Inhibitory Factor. The results obtained from this study will ideally provide a fundamental source in contemporary drug design in terms of both the key electronic properties underlying the possible reactivity features and toxicity. The pyrrole compounds were synthesized and characterized by spectroscopic tools (FT-IR, NMR). The DFT computations were performed to predict possible reactivity directions and sites. The ADMT (Absorption distribution, metabolism, and toxicity) features were calculated to evaluate the possible pharmacokinetics and bioavailability as well as the harmful effect in both medicinal and environmental respects. The molecular Docking studies were applied to compounds.imageÖğe An efficient new method of ytterbium(III) triflate catalysis approach to the synthesis of substituted pyrroles: DFT, ADMET, and molecular docking investigations(Elsevier Sci Ltd, 2023) Serdaroglu, Goncagul; Uludag, Nesimi; Ustun, ElvanIn this study, the one-pot synthetic methodology for the preparation of substituted pyrroles with diethyl acetylene-dicarboxylate is reported for the various pyrrole derivatives via the Trifimow synthesis process from oximes. This method also offers the literature as a cyclization pathway using a ytterbium triflate catalyst. Another importance of this study is the use of pyrrole derivatives in pharmaceuticals, biological processes, and agrochemicals. From this point of view, the development of a new catalyst in synthetic organic chemistry and the difference in the method is also important. The syntheses of the target substituted pyrroles are accomplished in high yields. Also, all synthesized structures were confirmed by 1H NMR, 13C NMR, and IR spectra. The DFT computations were leveraged for structural and spectroscopic validation of the compounds. Then, FMO and NBO analyses were subsequently employed to elucidate the reactivity characteristics and intramolecular interactions within these compounds. Also, ADMET indices were ascertained to assess potential pharmacokinetic properties, drug-like qualities, and possible adverse effects of these compounds. Last, optimized molecules were analyzed by molecular docking methods against crystal structures of Bovine Serum Albumin and Leukemia Inhibitory Factor, and their binding affinities, interaction details, and inhibition constants were determined.Öğe ÇİNKO-TRİFLAT KATALİZÖRÜ KULLANILARAK FARKLI SÜBSTİTÜYE İZOKUMARİN TÜREVLERİNİN SENTEZİ(2023) Uludag, NesimiGeniş bir doğal bileşik sınıfı oluşturan kumarinler, 19. yüzyıldan günümüze değin oldukça ilgi çeken ve çok sayıda pratik uygulamaya sahip olan organik bileşiklerdir. Kumarin bileşikleri, endüstride ve birçok ticari ilacın yapısında bulunan heterosiklik bileşikler olup, bu çalışmada izokumarinlerin sentezleri için farklı bir yöntem izlenerek metil 2-(feniletil) benzoat (1a-g) ve but-3-en-2-one (2)’nin çinko-triflat-katalizli tandem reaksiyonları gerçekleştirilmiştir. Söz konusu yöntemde, yüksek verimli ve çevre dostu bir reaksiyon oksijensiz ortamda gerçekleştirilmiş ve yeni bir katalizör kullanılarak hedeflenen izokumarin türevleri tek basamakta sentezlenmiştir. Diğer taraftan, elektron çekici ve elektron verici yan grupların reaksiyon oluşumuna ve verimine olan etkileri de araştırılmıştır. Özet olarak bu çalışmada, paladyum(II)-katalizli yüksek oranda regioselektif but-3-en-2-one ile cascada reaksiyonu ile geliştirilmiştir.Öğe Exploring an Alternative Synthetic Pathway for the Total Synthesis of (±)-Nordasycarpidol and (±)-Nordasycarpidone(Springer, 2023) Uludag, Nesimi; Nevarsa, Alev OrhanA total synthesis of the strychnos alkaloids, dasycarpidol and nordasycarpidone, has been accomplished from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetonitrile 1, which is the C-2 ethyl side chain of carbazole as well as carbazole-fused lactone 3 that is conveniently of the key azocino[4,3-b]indole skeleton 6. These syntheses of the target natural products are accomplished without a protecting group, which has a carbonyl group at the C-1 position of the carbazole. These alternative routes are accomplished by shortening the number of steps with high efficiency and also nordasycarpidol 8 synthesized for the first time in the literature. The structures of all the presently synthesized compounds were confirmed using spectroscopic methods (FT-IR, H-1 NMR, C-13 NMR).Öğe Facile and efficient method for Zn(OTf)2 catalyzed synthesis of isocoumarin derivatives and their antioxidant properties(Natl Inst Science Communication & Policy Research-Niscpr, 2023) Uludag, Nesimi; Nevarsa, Alev OrhanIn this research, the corresponding isocoumarin derivatives have been synthesized by tandem intramolecular cyclization of methyl 2-(phenylethynyl)benzoate 1 with ethyl acrylate. This process involves the synthesis of compounds 3-9 from compound 1 and 2 in one-pot reaction and zinc triflate as catalyst. The antioxidant properties of the synthesized isocoumarin have also been investigated by DPPH method.Öğe Green Synthesis of Pyrrole Derivatives Catalyzed by Molecular Sieves: DFT, ADMT, and Molecular Docking Investigations(Wiley-V C H Verlag Gmbh, 2024) Serdaroglu, Goncagul; Uludag, Nesimi; Ustun, ElvanA new synthetic methodology for the preparation by a different alternative method of five aryl pyrrole derivatives is produced from the corresponding ketoximes, giving diverse five-membered N-heterocycles in satisfactory yields. For the first time in literature, the synthetic catalyst molecular sieves were described. The simplicity and high response yield of this procedure are its standout qualities. Additionally, spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, elemental analysis) were used to confirm the structures of all synthesized compounds. FT-IR and NMR computations with B3LYP/6-311G** level by utilizing the G09 W package were performed to compare with observed data and evaluate the structural confirmation of novel pyrrole derivatives. Then, the lipophilic characterization and water solubility were computed to enlighten the physicochemical attitude. The ADMT properties were calculated to elucidate the possible bioavailability tendencies of the compounds and the adverse behaviour in terms of both medicinal and environmental. FMO analyses were also conducted to indicate/show the reactivity tendencies and possible regions. The molecular docking analyses of the optimized molecules were performed against Bovine Serum Albumin and Leukemia Inhibitory Factor. In conclusion, this study underscores the crucial role of green chemistry principles in developing novel synthetic methodologies, using environmentally benign catalysts like zeolite 3 angstrom. Green synthesis of substituted pyrroles via molecular sieves-catalyzed coupling was performed and characterized by spectroscopic tools. The DFT, lipophilicity, water solubility, molecular dockings, and ADMT computations were utilized to evaluate physicochemical and drug-likeness properties. imageÖğe Microwave-Assisted Synthesis of 5-Substituted 3-Amino-1,2,4-triazoles from Aminoguanidine Bicarbonate and Carboxylic Acids(Mdpi, 2024) Gumus, Mustafa Kemal; Gorobets, Mykola Yu.; Uludag, NesimiThe effect of the molar ratio between reagents, reaction time and temperature on the yield of 5-substituted 3-amino-1,2,4-triazoles obtained by the direct condensation of carboxylic acids with aminoguanidine bicarbonate under acid catalysis conditions was studied. As a result, a general green straightforward synthesis of the title compounds bearing aliphatic substituents or a phenyl ring was developed using sealed reaction vials under controlled microwave synthesis conditions that are suitable for the application of volatile starting carboxylic acids. Our straightforward synthetic method proposed in this work increases the synthetic accessibility of these widely used building blocks and therefore is able to significantly expand the structural diversity of compounds containing a triazole moiety for the needs of drug discovery.
