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Synthesis and Utilization of Selected Nitrogen Heterocycles
Mikušek, Jiří ; Pour, Milan (advisor) ; Veselý, Jan (referee) ; Bureš, Filip (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Inorganic and Organic Chemistry Candidate: Mgr. Jiří Mikušek Supervisor: prof. RNDr. Milan Pour, PhD. Title of Doctoral Thesis: Synthesis and Utilization of Selected Nitrogen Heterocycles The thesis is divided into two parts, both dealing with the synthesis of pyridine and pyrimidine derivatives. The first one is focused on the cyclization of enynes with gold(I) catalysts. Main attention is paid to the synthesis of various acyclic precursors starting from propargylamines, their addition to propiolates and Sonogashira cross-coupling. The mechanism of the cyclization with (TFP)AuCl is then discussed in detail. Prepared dihydropyridines were converted to pyridines or tetrahydropyridines. A precursor of the antidepressant drug paroxetine was prepared. The second part deals with quinazoline alkaloids with pyrimidine moiety and their structural variations towards potential organocatalysts and biologically active compounds. Therein new types of organocatalysts based on the structure of vasicine were prepared and screened on model aldolization and addition reactions. Prepared compounds were tested for bronchodilator activity.
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Preparation of asymmetrically substituted diphenylacetylenes usable in molecular electronics
Rejšek, Jan ; Jindřich, Jindřich (advisor) ; Veselý, Jan (referee)
Preparation of asymetrically substituted diphenylacetylenes usable in molecular electronics Abstract This bachelor's work deals with synthesis of assymetrically substituted diphenylacetylenes and their transformation into (η4 -cyclobutadiene)-(η5 - cyclopentadienyl)cobalt complexes, which should be used and researched as molecular rotors. Multistep synthesis concerning conversion of primary arylamines into tertiary by N-permethylation, nucleophilic acyl substitution and Sonogashira coupling was prepared asymmetrically substituted diphenylacetylene with, which consequently underwent cycloaddition [2 + 2] with cyclopentadienyldicarbonylcobalt. Creating (η4 -cyclobutadiene)-(η5 -cyclopentadienyl)cobalt complexe was identified by MS. Keywords: diphenylacetylene, Sonogashira coupling, (η4 -cyclobutadiene)- (η5 -cyclopentadienyl)cobalt complex, cycloaddition [2 + 2], molecular rotor
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Preparation of organocatalysts derived from thiourea containing saccharide units
Řehůřková, Tereza ; Veselý, Jan (advisor) ; Smrček, Stanislav (referee)
4 ABSTRACT This diploma thesis is focused on the synthesis of new bifunctional thiourea organic catalysts containing a carbohydrate moiety, in particular D-glucose with modification on the primary hydroxyl group. The first part of this diploma thesis describes a modification of synthesis of the known bifunctional thiourea catalyst with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose and (1R,2R)-diaminocyclohexane. The second part is dedicated to the synthesis of new bifunctional thiourea catalysts with modification of the carbohydrate moiety. We focused on per-O-acetyl-β-D-glucopyranose derivatives with pefluoroalkyl moiety on the primary hydroxyl group. We examined different ways of the preparation of 6-O-perfluoroalkylated glucose derivatives. These perfluoroalkylated carbohydrate compounds were transformed into corresponding glycosyl isothiocyanates. Those derivatives upon treatment of (1R,2R)-diaminocyklohexane or 3,5- bis(trifluormethyl)aniline afforded new bifunctional thiourea organocatalysts.
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Organocatalytic asymmetric synthesis of various organic compounds from α,β-unsaturated aledyhes
Kamlar, Martin ; Veselý, Jan (advisor) ; Trnka, Tomáš (referee)
With regard to a fast development in the field of fluoroorganic chemisty, the intention of this diploma thesis is focused to utilize of organocatalysis by secondary amines as catalysts for preparation enantiomerically pure compounds containing fluorine atom in its structure. The preparation of these subsances is realized by way of nucleofilic addition to α,β- unsaturated aldehydes using suitable fluorine containing nuclephilic agent 1-(fluoronitromethylsulphonyl)benzene, to get appropriate 1,4-adduct.
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Preparation of alfa(1-4)-linked disaccharides containing D-glukosamine units
Škríba, Anton ; Veselý, Jan (advisor) ; Jindřich, Jindřich (referee)
Abstract The aim of this diploma thesis is a preparation of disaccharide composed from two glucosamine units with 1,2-cis-(1→4)-O-glycosidic bond with the attached linker on reducing end, containing an azide functional group. The first part is focused on synthesis of glycosyl acceptor and glycosyl donor, derived from D-glucosamine, suitable for the construction of 1,2-cis-(1→4)-O-glycosidic linkage. The second part of this work describes the optimization of the glycosylation reaction conditions and also subsequent transformation of disaccharide GlcNAc-α-(1→4)-GlcNAc skeleton.
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Aminocarbonydrates as part of cyclic polyamines
Vacková, Zuzana ; Lorenc, Miroslav (advisor) ; Veselý, Jan (referee)
Magnetic resonance imaging is one of the imaging methods that are needed in medicine for diagnostic purposes. This method neither exposes the patient to X-rays, nor any other negative effects on the human organism are known by then. Another significant advantage of MRI is its ability to achieve high contrast even between structurally very similar tissues. The contrast agents commonly used with the magnetic resonance imaging help heighten this ability. Part of these contrast agents is a metal ion, the ion gadolinium (GdIII) is the most commonly used nowadays. But it must be complexed by a suitable ligand. This work deals with the synthesis of a number of potentially suitable model ligands. The saccharide component is even a part of these ligands. This component should enable to achieve a greater solubility of the complex or the possibility of linking other additional saccharide units, another ligand or a detecting group. Several theoretical paths leading to the final fabric were created. Not all of them led to the target, only one was successful. The produced macrocycle is the potentially applicable ligand for complexation with GdIII or other metal ion, it means a good part of the new potential contrast agent.
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