Browsing by Author "Sahin, Ertan"

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A Green Protocol for Simple One-Pot Synthesis of New Pyrimidine Derivatives Both Microwave Irradiation and Conventional Heating: Reactions, Characterization, and Theoretical Calculations
(Wiley, 2019) Akbas, Esvet; Ruzgar, Adem; Sahin, Ertan; Ergan, Erdem
In this research, 5-benzoyl-6-phenyl-4-(4-trifluoromethylphenyl)-2-{oxo and thioxo}-3,4-dihydro-1H-pyrimidines (1, 2) were synthesized by using multicomponent cyclocondensation reaction under microwave irradiation and classical heating. Compounds 3, 4, 6, 7, and 8 obtained reactions of 5-benzoyl-6-phenyl-4-(4-trifluoromethylphenyl)-2-thioxo-3,4-dihydro-1H-pyrimidine (1) and acetic anhydride, diethyl 2-bromomalonate, bromoacetic acid, 3-bromopropionic acid, methyl iodide, respectively. Compound 4 was both acetylated and hydrolyzed in acetic acid to give compound 5. The structures of all compounds were determined by using spectroscopic techniques like FT-IR, H-1/C-13 NMR, and elemental analyses, and the structures of compounds 1 and 3 were analyzed by X-ray crystal analysis. In addition, the quantum chemical parameters and full geometry optimizations for all compounds were computed using density functional theory based on B3LYP and the 6-31G (d, p) basis set.
Metal- and Base-Free Combinatorial Reaction for C-Acylation of 1,3-Diketo Compounds in Vegetable Oil: the Effect of Natural Oil
(Amer Chemical Soc, 2014) Menges, Nurettin; Sahin, Ertan
C-acylation of 1,3-diketo compounds has been done successfully employing 1,3 diketo compounds, oxalyl chloride, and phenol derivatives through metal, base, and toxic solvent-free protocol. Dioxinone ring-bearing 1,3,3' tricarbonyl moiety was also obtained in the same conditions using salicyl aldehyde. All reactions were carried out in vegetable oil.
Microwave-Assisted Synthesis of New Dihydropyrimidine Derivatives and Mechanism of the Reactions
(Bentham Science Publ Ltd, 2013) Akbas, Esvet; Sahin, Ertan; Yildiz, Ela; Anil, Baris; Akyazi, Inci
5-benzoyl-4-aryl-6-phenyl-1,2,3,4-tetrahydro-2-thioxopyrimidines were synthesized via Biginelli cyclocondensation reaction. The diethyl 2-(4-aryl-5-benzoyl-6-phenyl-3,4-dihydropyrimidin-2(1H)-ylidene) malonates were prepared by the reaction of thioxopyrimidines with diethyl 2-bromomalonate in dioxane/pyridine (10/1 v:v) under microwave irradiation and conventional conditions. The reaction of diethyl 2-(5-benzoyl-4,6-phenyl-3,4-dihydropyrimidin-2(1H)ylidene) malonate with hydrazine hydrate and urea yielded the compounds of (E)-ethyl 2-(5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-ylidene)-3-hydrazinyl-3-oxopropanoate and (E)-ethyl 2-(5-benzoyl-4,6-diphenyl-3,4dihydropyrimidin-2(1H)-ylidene)-3-oxo-3-ureidopropanoate, respectively. All of these new derivatives were characterized by analytical and spectroscopic studies. The structure of the diethyl 2-(5-benzoyl-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-lidene) malonate was identified by a single crystal X-ray diffraction analysis, and the reaction mechanism was also discussed.
N-Acetylation of Methyl Hydrazones With Acetic Acid in Presence of Pdcl2
(Taylor & Francis inc, 2023) Aslanoglu, Furgan; Sahin, Ertan
Organic compounds such as acetic anhydride or acetyl chloride are generally used to form amide bonds by the acetylation of a nitrogen atom. However, it is not possible to use this traditional method for hydrazine derivatives. In this article, a new synthesis method has been developed for the formation of a new amide bond via the acetylation of methyl hydrazones with acetic acid. In the development of this unprecedented synthesis method, more than one catalyst was used as the Lewis acid. PdCl2 was identified as the most suitable catalyst for this reaction. In addition, more than one solvent experiment was carried out for the optimization of this method and experiments were carried out to provide the most optimal conditions for catalyst loading. In addition, the applicability of this method to various hydrazone derivatives was tested. The structures of nine new amide bond-containing acetylated methyl hydrazones prepared by this synthesis method were elucidated using 1D-NMR, 2D-NMR, LCMS and X-Ray.
Synthesis of Pyrrole-Fused C,n-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values
(Amer Chemical Soc, 2016) Ozer, Merve Sinem; Menges, Nurettin; Keskin, Selbi; Sahin, Ertan; Balci, Metin
The AgOTf-catalyzed reaction of C-2 substituted pyrrole hydrazones having an N-propargyl group was studied. The selective 6-endo-dig mode of cyclization was observed, giving rise to the formation of pyrrole-fused C,N-cyclic azomethine imine derivatives. The reaction of one azomethine imine derivative with various dipolarophiles resulted in the formation of cycloadducts having a pyrazolopyrrolopyrazine skeleton. The aromaticity of C,N-cyclic azomethine imines as well as that of pyrazolopyrrolopyrazines was determined by calculating of nucleus-independent chemical shifts values.
Synthesis of the 3,5-Diphenyl and Cytogenetic and Oxidative Alterations After Exposure of Cultured Human Whole Blood Cells
(Taylor & Francis As, 2017) Akbas, Esvet; Celikezen, Fatih Caglar; Turkez, Hasan; Ozdemir, Ozlem; Ruzgar, Adem; Ergan, Erdem; Sahin, Ertan
The 3,5-diphenyl-1H-pyrazole was obtained by condensation reaction of dibenzoylmethane and thiosemicarbazide in acetic acid under conventional heating and microwave irradiation method. The structure of the 3,5-diphenyl-1H-pyrazole confirmed by IR, H-1, and C-13 NMR and X-ray diffraction and the geometry optimization was carried out using density functional theory (DFT) methods at B3LYP/6-31G, 6-31G(d), 6-31G(d, p), 6-311G(d, p), 6-311G(2d, 2p), 6-31+G(d, p), 6-311++G(d, p) levels. In addition, cytotoxic and oxidative effects were investigated in cultured human peripheral blood cells.
Synthesis, Theoretical Calculation, Electrochemistry and Total Antioxidant Capacity of 5-Benzoy1 and Derivatives
(Elsevier, 2017) Ergan, Erdem; Akbas, Esvet; Levent, Abdulkadir; Sahin, Ertan; Konus, Metin; Seferoglu, Nurgul
5-Benzoy1-6-pheny1-4-(4-mehtoxyphenyI)-1,2,3,4-tetrahydro-2-thioxopyrimidine (1) have been prepared via Biginelli cyclocondensation reaction in acetic acid under reflux condition in good yield. The structure of 1 was determined by using spectroscopic techniques like H-1/C-13 NMR and elemental analyses. And also their molecular characterizations of compounds were analyzed by X-ray crystal analysis. A series of novel pyrimidine derivatives were obtained by reaction compound I with various reactive. All synthesized pyrimidine derivatives and related keto and enol tautomeric forms have been optimized geometrically with DFF in Gaussian at the B3LYP/6-31 + G (d, p) level in order to obtain information about the 3D geometries and electronic structures. The results showed that the keto tautomer is more stable than enol tautomer. However, the non-linear optical (NLO) properties were evaluated theoretically. The electrochemical properties of the novel compounds were investigated by CV and DPV. In addition, the total antioxidant capacities of all new synthesized compounds were measured in vitro by ABTS assay. (C) 2017 Elsevier B.V. All rights reserved.
Transition Metal(Ii) Complexes of a Novel Symmetrical Benzothiazole-Based Ligand: Synthesis, Spectral/Structural Characterization and Fluorescence Properties
(Springer/plenum Publishers, 2014) Gulcan, Mehmet; Karatas, Yasar; Isik, Sema; Ozturk, Gulsiye; Akbas, Esvet; Sahin, Ertan
2,6-bis (benzothiazol-2-yl)-4-(tert-butyl) phenol ligand (HL) derived from o-aminothiophenol and 4-tert-butyl-2,6-diformylphenol was synthesized and characterized by using elemental analysis, FTIR, X-ray crystallographic analysis, H-1 and C-13-NMR and UV-vis spectra. Its complexes with Cu (II), Ni (II) and Co (II) were prepared and isolated as solid products and characterized by elemental analysis, spectral techniques as well as magnetic susceptibility. The FTIR spectra showed that the benzothiazole-based ligand under investigation behaves as a bidentate ligand. The UV-vis spectra and magnetic moment data suggested an octahedral geometry around Ni (II) and Co (II) complexes, and tetragonal geometry for Cu (II) complex. Moreover, the evaluation of absorption and emission properties of the ligand and its complexes were carried out in different solvents. The ligand and its complexes showed absorption maxima in the range of 275 - 432 nm, and emission maxima from 367 to 581 nm in toluene, tetrahydrofuran and ethyl acetate.