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Öğe Crystal Structure of 4-Bromo-3,4-Dichloro-1-(1-Morpholinyl)-1-(Decylsulfanyl)-2-Nitro-Buta-1,3-Diene(Springer/Plenum Publishers, 2010) Ibis, Cemil; Deniz, Nahide Gulsah; Tuyun, Amac FatihThe compound 4-bromo-3,4-dichloro-1-(1-morpholinyl)-1-(decylsulfanyl)-2-nitro-buta-3-diene was synthesized from the reaction of 4-bromo-1,3,4-trichloro-1(decylsulfanyl)-2-nitro-buta-1,3-diene with morpholine and characterized by elemental analysis, IR spectrum, UV spectra, H-1 NMR, C-13 NMR and X-ray single crystal determination. In the title compound, C18H29BrCl2N2O3S, crystallizes in the monoclinic space group P2(1)/c, a = 15.8326(4) angstrom, b = 8.9915(10) angstrom, c = 16.7528(5) angstrom, beta = 100.808(10)degrees, V = 2,342.6(3) angstrom(3), Z = 4, R-1 = 0.0590 and wR(2) = 0.0940. The morpholine ring adopts a chair conformation. The morpholine ring and the butadiene group are inclined at an angle of 113.4 (1)degrees. The butadiene unit is not planar as can be expected if the two double bonds are fully conjugated.Öğe Nucleophilic substitution reactions of 1,4-naphthoquinone and biologic properties of novel S-, S,S-, N-, and N,S-substituted 1,4-naphthoquinone derivatives(Springer Birkhauser, 2014) Ibis, Cemil; Tuyun, Amac Fatih; Bahar, Hakan; Ayla, Sibel Sahinler; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya.; Komarovska-Porokhnyavets, OlenaA novel series of S-, S,S-, N- and N,S-substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. Among the synthesized compounds especially 10a and 11b have been discovered as an antibacterial or antifungal agents, and 15f is the most effective compound against M. luteum as potent antifungal. The structures of the novel products were characterized by micro analysis, UV/Vis, H-1 NMR, C-13 NMR, and MS. The electrochemical properties of some of the novel 1,4-naphthoquinone derivatives were also investigated by cyclic voltammetry.Öğe REACTIVITY STUDY OF 2,4-DINITROBUTA-1,3-DIENES TOWARDS MONO-, POLY-, AND PERSULFANYL CONJUGATED DIENES BY REGIOSPECIFIC VINYL GROUP ACTIVATION(Taylor & Francis Ltd, 2012) Ibis, Cemil; Tuyun, Amac FatihPolyhalogenated nitrobuta-1,3-dienes are unique reagents in organic synthesis and have been employed in several well-known and recently developed areas of application. This study describes the scope and application of 1,1,3,4-tetrachloro-2,4-dinitrobuta-1,3-diene in organic synthesis as well as methods for the preparation of poly-and perfunctionalized 2,4-initrobuta-1,3-dienes, and characterization of all obtained compounds.Öğe Regioselective Substitution of Vinyl Halide by n-Alkyl Mercaptans and Subsequent Reactions with Versatile Cyclic Secondary Amines(Asian Journal Of Chemistry, 2010) Ibis, Cemil; Tuyun, Amac Fatih; Aydinli, GoeksinHerein, we have described the preparation of several S-subtituted nitrobuta-1,3-dienes (3a-b) using the 4-bromo-1,1,3,4-tetrachloro-2-nitrobuta- 1,3-diene (1) with mercaptans (2a-b). Afterwards, N,S-substituted nitrobuta-1,3-diene compounds (5a, 7b and 9a-j) are obtained from the interaction of versatile secondary amines with the substituted product S-substituted nitrobuta-1,3-dienes (3a-b) in dichloromethane. Synthesized compounds have been characterized by using IR and NMR spectroscopy methods. Structural characterization is supported by elemental analysis and by mass spectrometry with accurate mass measurement of the molecular ion.Öğe Synthesis and Antibacterial and Antifungal Properties of Novel S-, N-, N,S-, and S,O-Substituted 1,4-Naphthoquinone Derivatives(Taylor & Francis Ltd, 2013) Ibis, Cemil; Tuyun, Amac Fatih; Ozsoy-Gunes, Zeliha; Ayla, Sibel Sahinler; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya; Komarovska-Porokhnyavets, OlenaA novel series of substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 2,2,3,3-alkoxy substituted naphthoquinones, S,O-substituted naphthoquinone, and N,S-substituted naphthoquinone derivatives are the most potent antifungals against C. tenuis. 2,3-Thio-2,3-alkoxy substituted naphthoquinones are the most effective antifungal compounds against A. niger. Supplemental materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsto view the free supplemental file.Öğe Synthesis and biological evaluation of novel nitrogen- and sulfur-containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents(Elsevier France-Editions Scientifiques Medicales Elsevier, 2011) Ibis, Cemil; Tuyun, Amac Fatih; Ozsoy-Gunes, Zeliha; Bahar, Hakan; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya.; Komarovska-Porokhnyavets, Olena1,4-Naphthoquinones are unique reagents in organic synthesis and have been employed in several well known and recently developed areas of application. Furthermore, these 1,4-naphthoquinones have demonstrated high reactivity in nucleophilic vinylic substitutions, in the preparation of sulfurated, (hetero)cyclic and several other transformations. This study describes the synthesis and biological evaluation of derivatives of monosulfurated naphthalene-1,4-dione (3), 3-chloro-2-ethoxy-naphthalene-1,4-dione (4), disulfurated naphthalene-1,4-dione (5), and symmetrical bis-1,4-naphthoquinones (7, 9) were obtained from the reaction of 2,3-dichloro-naphthaquinone (1) with S-, O-substituted mono-, di-, and tetrathiols, respectively. The structures of the novel products were characterized by spectroscopic methods. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.Öğe The Synthesis of New S- and N,S-Substituted Halo Nitro Dienes by the Reactions of 1-Bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene with Thiols and Cyclic Amines(Taylor & Francis Ltd, 2010) Ibis, Cemil; Tuyun, Amac Fatih; Aydinli, GoksinThe substituted products alkyl(aryl)thio-tetrahalo-3-nitrobuta-1,3-dienes 3a-b were obtained from the reactions of 1-bromo-1,2,4,4-tetrachloro-3-nitrobuta-1,3-diene (1) with thiols. Further reactions of the substituted product alkyl(aryl)thio-tetrahalo-3-nitrobuta-1,3-dienes 3a-b in dichloromethane reacted with piperazine derivatives and morpholine to generate 5a-b and 7a-l. The structures of the new compounds were determined by microanalysis and spectroscopic data.Öğe Synthesis of novel 1,4-naphthoquinone derivatives: antibacterial and antifungal agents(Springer Birkhauser, 2013) Ibis, Cemil; Tuyun, Amac Fatih; Bahar, Hakan; Ayla, Sibel Sahinler; Stasevych, Maryna V.; Musyanovych, Rostyslav Ya.; Komarovska-Porokhnyavets, OlenaA novel series of substituted 1,4-naphthoquinone derivatives was synthesized and evaluated for antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 3a and 9 are the most effective compounds against M. luteum as potent antibacterial and C. tenuis and A. niger as potent antifungal. These two compounds are promising as biologically active compounds.Öğe Synthetic Exploitation of Halogenated Alkenes Containing EWG: Polysubstituted Sulfanyl Dinitro Butadienes from Sequential Nucleophilic Substitutions(Bentham Science Publ Ltd, 2011) Ibis, Cemil; Tuyun, Amac FatihOur novel approach starts from a 1,1,3,4-tetrachloro-2,4-dinitrobuta-1,3-diene (5) being one of the most prominent members of this relatively new class of synthetic building blocks. Because of its multifunctional chemical behavior, polyhalogenated nitrobuta-1,3-dienes proved to be versatile reagents in the synthesis of a large variety of sulfurated, (hetero) cyclic, and acyclic derivatives. We describe our studies concerning successive nucleophilic vinylic substitution reactions of dinitrobuta-1,3-diene in order to establish the reactivity profile of this precursor and determine whether this precursor could be used for the synthesis of many dinitrodiene analogues offering new methodology for the synthesis of polyfunctional precursors that are difficult to access. Some of the resulting perfunctionalized 2,4-dinitrobuta-1,3-dienes are subjected to further transformations to give promising candidates with respect to biological activity.
