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Murat Cakici Mustafa Catir Semistan Karabuga Hamdullah Kilic Sabri Ulukanli Medine Gulluce Furkan Orhan 《Tetrahedron: Asymmetry》2010,21(16):2027-2031
A simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia coli WP2uvrA tester strains at 0.01, 0.1, and 1 μg/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1 μg/plate dose. 相似文献
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Cationic polyelectrolytes containing quaternary nitrogen atoms within the main chain were prepared via condensation polymerization of epichlorhydrin (ECH) with benzyl amine (BA). Polyelectrolytes having different molecular weights were obtained by varying the ECH/BA mole ratio. Cationic polymers were characterized by 1H-NMR and gel permeation chromatography. The antimicrobial activity of the polymers was tested against bacteria, yeast, and fungi. 相似文献
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8-Phenylmenthol derived α,β-unsaturated esters were aziridinated highly diastereoselectively using 3-acetoxyamino-2-ethylquinazolinone. The yields of these aziridines were greatly improved in the presence of hexamethyldisilazane. 相似文献
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Murat CakiciMustafa Catir Semistan KarabugaSabri Ulukanli Hamdullah Kilic 《Tetrahedron: Asymmetry》2011,22(3):300-308
A series of (1S,1′S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. 相似文献
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Mustafa Catir Murat Cakici Semistan Karabuga Sabri Ulukanli Ertan Şahin Hamdullah Kilic 《Tetrahedron: Asymmetry》2009,20(24):2845-2853
Optically active propargylic alcohols are important chiral-building blocks in asymmetric synthesis, while the asymmetric addition of a terminal alkyne to an aldehyde is one of the most important procedures to prepare these chiral-building blocks. In this work, a family of chiral 4,4′-biquinazoline alcohols has been conveniently prepared from the easily accessible (S)-2-acetoxycarboxylic acid chlorides by reaction sequences beginning with condensation and followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection in addition to being examined as potential ligands in the enantioselective addition of phenylacetylene to aldehydes. These chiral ligands can be combined with Ti(OiPr)4 and then used to catalyze the asymmetric addition of zinc acetylide, produced in situ by the reaction of phenylacetylene with diethylzinc, to aldehydes. The best enantiomeric excess obtained in this study was 75%. 相似文献
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Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the optimised reaction conditions, the best enantioselectivity was obtained using l-lactic acid derived 4-phenylquinazolinol and apart from the cyclohexylcarbaldehyde derivative, 16 propargylic alcohols were then synthesised in moderate to excellent enantiomeric excess from 53% to 97%. 相似文献
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Karabuga S Cakici M Kazaz C Sahin E Kilic H Ulukanli S 《Organic & biomolecular chemistry》2011,9(22):7887-7896
A series of sulfoxides were sulfoximinated using oxidative addition of 3-aminoquinazolinones by lead tetraacetate in the presence of hexamethyldisilazane. They were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde. 相似文献
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The reaction of 3-acetoxyaminoquinazolinone (QNHOAc) with various sulfoxides in the presence of HMDS as an acetic acid scavenger, afforded the corresponding sulfoximides in good yields. Sulfoximidation of phenyl methyl sulfoxide using a Q*NHOAc having a stereogenic centre on its 2-position gave the products in 1.3:1 ratio of diastereomers. 相似文献
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