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Öğe 1,4-diferrocenylbutane-1,4-dione(Blackwell Publishing, 2008) Tombul, Mustafa; Bulut, Adnan; Guven, Kutalmis; Buyukgungor, OrhanIn the crystal structure of the title compound, [Fe-2(C5H5)(2)-(C14H12O2)], each carbonyl group is coplanar with the adjacent cyclopentadienyl ring, thus maximizing the pi-orbital overlap and electronic interactions between the groups. In the crystal structure, there are inter-and intramolecular C-H center dot center dot center dot O contacts.Öğe Alkyl Lewis Acid Catalyzed Syntheses of Dicarbonyl Ferrocenes(Asian Journal Of Chemistry, 2010) Tombul, Mustafa; Gemici, S.; Bulut, AdnanA series of diferrocenoyl compounds; succinyl (1), glutaryl (2), adipoyl (3), suberoyl (4) and sebacoyl ferrocene (5) were synthesized from the reaction of ferrocene with EtAlCl(2). Compared to the conventional methods reported in the literature, the yields obtained from these reactions are found to be higher than the typical catalyst.Öğe Application of FAM ligands in the metal-promoted catalytic enantioselective synthesis of organic compounds(Scientific Technical Research Council Turkey-Tubitak, 2009) Dogan, Oezdemir; Garner, Philip P.; Bulut, AdnanNovel ferrocenyl substituted aziridinyl methanol (FAM) ligands were synthesized and successfully used in metal-promoted catalytic enantioselective azomethine ylide cycloadditions, diethylzinc additions to enones, alkynylzinc additions to aldehydes, diethylzinc additions to aldehydes, and Henry reactions. These reactions are summarized in this report.Öğe Catalytic asymmetric nitroaldol (Henry) reaction with a zinc-Fam catalyst(Amer Chemical Soc, 2008) Bulut, Adnan; Aslan, Ayhan; Dogan, OezdemirFerrocenyl-substituted aziridinylmethanol (Fam-1) was used as a catalyst with zinc for the asymmetric nitroaldol (Henry) reaction. This catalyst worked with a variety of aldehydes (aromatic, aliphatic, alpha,beta-unsaturated, and heteroaromatic) and alpha-ketoesters to give the nitroaldol product in up to 97% yield and 91% ee. The chiral ligand call be recovered and recycled Without losing its activity.Öğe Catalytic enantioselective addition of diethylzinc to aldehydes using aziridine based chiral ligands(Pergamon-Elsevier Science Ltd, 2007) Bulut, Adnan; Aslan, Ayhan; İzgü, Enver Cağrı; Doğan, ÖzdemirThe readily available ferrocenyl substituted aziridinylmethanol 1 (FAM-1) was used as a chiral catalyst in the diethylzinc addition reaction to aromatic and aliphatic aldehydes to give secondary alcohols in high yields and up to 99% enantiomeric excess at room temperature. The catalyst can be recovered and used without losing its activity. (c) 2007 Elsevier Ltd. All rights reserved.Öğe Chiral phosphine oxide aziridinyl phosphonate as a Lewis base catalyst for enantioselective allylsilane addition to aldehydes(Pergamon-Elsevier Science Ltd, 2015) Dogan, Ozdemir; Bulut, Adnan; Tecimer, M. AliA series of chiral Lewis bases, phosphine oxide ferrocenyl aziridinyl methanol 1-4, phosphinyl aziridinyl phosphonates 5 and 6, and phosphine oxide aziridinyl phosphonates 7 and 8 were screened for allylsilane additions to aldehydes. Among the Lewis bases, 8 was found to catalyze the reaction by forming the product in up to 94% yield and with 77% ee. (C) 2015 Elsevier Ltd. All rights reserved.Öğe Copper-catalyzed asymmetric conjugate addition of diethylzinc to substituted chalcones using a chiral phosphine ligand(Pergamon-Elsevier Science Ltd, 2011) Dogan, Ozdemir; Bulut, Adnan; Polat, Savas; Tecimer, M. AliA series of chiral phosphine PFAM and phosphine oxide POFAM ligands were studied for the copper-catalyzed asymmetric diethylzinc addition to enones. One of these ligands, PFAM2, was an efficient catalyst with a variety of enones to give conjugate addition products in up to 96% yield and 92% ee. (C) 2011 Elsevier Ltd. All rights reserved.Öğe Copper-catalyzed asymmetric conjugate addition of diethylzinc to substituted chalcones using a chiral phosphine ligand (vol 22, pg 1601, 2011)(Pergamon-Elsevier Science Ltd, 2012) Dogan, Ozdemir; Bulut, Adnan; Isleyen, Alper; Polat, Savas; Tecimer, M. Ali[Abstract No tAvailable]Öğe Crystal structure of 1-ferrocenyl-(3-methyl-1-phenylaziridin-2-yl)-methanone, (C5H5)Fe(C16H16NO)(2005) Bulut, Adnan; Güven, K.; Dogan, Özdemir; Zeytinci, S.C21H21FeNO, monoclinic, P121/a1 (no. 14), a = 7.329(7) Å, b = 17.343(3) Å, c = 13.618(5) Å, ? = 95.02°, V = 1724.3 Å3, Z = 4, Rgt(F) = 0.044, wRref(F2) = 0.111, T= 293 K. © 2005, Oldenbourg Wissenschaftsverlag GmbH, Rosenheimer Str. 145, 81671 München. All rights reserved.Öğe Crystal structure of dimethylammonium bis(naphthalene-2,3-diolato) borate, C22H20BNO4(Walter De Gruyter Gmbh, 2018) Tombul, Mustafa; Guven, Kutalmis; Bulut, Adnan; Svoboda, Ingrid; Fuess, HartmutC22H20BNO4, monoclinic, C2/c (no. 15), a = 32.303(4) angstrom, b = 8.2703(6) angstrom, c = 7.3876(6) angstrom, beta = 92.889(8)degrees, V = 1971.1(3) angstrom(3), Z = 4, R-gt(F) = 0.0978, wR(ref)(F-2) = 0.2063, T = 298 K.Öğe Efficient synthesis of ferrocenylenones by Friedel-Crafts acylation with EtAlCl2-Me3Al(Elsevier Science Sa, 2005) Doğan, Özdemir; Şenol, Volkan; Zeytinci, Serhat; Koyuncu, Hasan; Bulut, AdnanEfficient synthesis of ferrocenyl en ones using a Friedel-Crafts acylation reaction is described. Acryloyl, methacryloyl, crotonoyl, cinnamoyl, and beta-methylcrotonoyl chlorides react with ferrocene in the presence of a Lewis acid (EtAlC2 or EtAlCl2-Me3Al) to give the corresponding ferrocenyl en ones (acryloyl, methacryloyl, crotonoyl, cinnamoyl, and methylcrotonoylferrocenes) in good isolated yields. Besides ferrocenylenones, chloroactylferrocene is also synthesised by this method. (C) 2004 Elsevier B.V. All rights reserved.Öğe Erratum: Copper-catalyzed asymmetric conjugate addition of diethylzinc to substituted chalcones using a chiral phosphine ligand (Tetrahedron: Asymmetry (2011) (1601-1604))(2012) Dogan, Özdemir; Bulut, Adnan; Ileyen, Alper; Polat, Savaş; Ali Tecimer, M.[No abstract available]Öğe Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation(Elsevier Sci Ltd, 2021) Sert, Mustafa; Isilar, Ozer; Yaglioglu, Ayse Sahin; Bulut, AdnanN-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NMR, 13C NMR, FT-IR, Mass and optical rotations. This is, to the best of our knowledge, the unique example of N-sugar aziridine synthesis. Diastereomeric effects for prostate (PC3) and cervix (HeLa) cancers were screened and it has been observed that the epimers bearing the same sugars showed different results against PC3 and HeLa cancer cells. The novel sugar aziridines were investigated as promising prodrug candidates for prostate cancer (PC3) therapy. Moreover, the drug likeness calculations (Lipinski's rule, physicochemical properties, lipophilicity, solubility, pharmacokinetics and bioavailability radar) have indicated that the sugar aziridines can be good candidates as oral drugs.Öğe New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions(Amer Chemical Soc, 2006) Doğan, Özdemir; Koyuncu, Hasan; Garner, Philip; Bulut, Adnan; Youngs, Wiley J.; Panzner, MatthewA new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.Öğe Non-Acidic Mediated Friedel-Craft Reaction of Thiophene Using EtAlCl2(Asian Journal Of Chemistry, 2013) Unver, Halil; Biyikoglu, Mutluhan; Bulut, AdnanSince alkyl Lewis acids are Bronsted bases, they give a non-acidic reaction media. In this context, acylation of thiophene is investigated in the presence of EtAlCl2 and non-acidic media. Besides 8 examples of thiophene, one example for pyrrole is synthesized in moderate to high yields (up to 99 %).Öğe ORGN 188-A new method for the synthesis of racemic and chiral aziridine 2-phosphonates(Amer Chemical Soc, 2009) Doğan, Özdemir; Bulut, Adnan; Aslan, Ayhan; Tan, Serkan; Babiz, Hakan…Öğe ORGN 90-A new phosphorous based chiral catalyst for the catalytic asymmetric synthesis of pyrrolidines via 1,3-dipolar cycloadditions of azomethine ylides(Amer Chemical Soc, 2009) Doğan, Özdemir; Eroksuz, Serap; Garner, Philip P.; Bulut, Adnan…Öğe Pyrolysis of Table Sugar(Hindawi Publishing Corporation, 2013) Bulut, Adnan; Karagoz, SelhanTable sugars were pyrolyzed at different temperatures (300, 400, and 500 degrees C) in a fixed-bed reactor. The effect of pyrolysis temperature on yields of liquid, solid, and gaseous products was investigated. As expected the yield of liquid products gradually increased and the yield of solid products gradually decreased when the pyrolysis temperature was raised. The yield of liquid products was greatest (52 wt%) at 500 degrees C. The composition of bio-oils extracted with diethyl ether was identified by means of gas chromatography mass spectrometry (GC-MS), nuclear magnetic resonance (H-1-NMR), and Fourier transform infrared spectroscopy (FTIR). The following compounds were observed in bio-oils produced from the pyrolysis of table sugar at 500 degrees C: 1,4: 3,6-dianhydro-alpha-d-glucopyranose, 5-(hydroxymethyl) furfural, 5-acetoxymethyl-2-furaldehyde, and cyclotetradecane liquid product. The relative concentration of 5-(hydroxymethyl) furfural was the highest in bio-oils obtained from pyrolysis of table sugars at 500 degrees C.Öğe Synthesis and biological activity of ferrocenyl furoyl derivatives(Taylor & Francis Inc, 2017) Tombul, Mustafa; Bulut, Adnan; Turk, Mustafa; Ucar, Busra; Isilar, OzerDue to the fact that ferrocene and furan derivatives have long been known to be one of the most biologically active compounds, preparation of their new derivatives might serve a very important purpose. Herein, five furoyl ferrocenes were synthesized via EAS reaction utilizing AlCl3-EtAlCl2 Lewis acids. The compounds 1-5 were obtained in moderate yields and characterized by IR, H-1-NMR, C-13-NMR, and mass spectrometry. Although toxicity increases with concentration, at 100 mu g/mL concentration, the protection of cell viability was observed to be 70% level. At 50 mg/mL concentration, apoptosis in cancer cells observed was 63 +/- 4% leading to high apoptosis ratio for the compound 3. For the compounds (1-5), the necrotic effects were found to be between 21% and 39% at 50 mu g/mL concentration.Öğe Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone(ELSEVIER SCI LTD, 2020) Isilar, Ozer; Bulut, Adnan; Yaglioglu, Ayse Sahin; Demirtas, Ibrahim; Arat, Esra; Turk, MustafaA series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, H-1 NMR, C-13 NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 mu M against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 mu M) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 mu M, 1.51 mu M and 1.02 mu M, respectively while 5-FU has 2.51 mu M. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.
