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Application of a Bolm ligand analog in catalysis
Malatinec, Štefan ; Kotora, Martin (advisor) ; Matoušová, Eliška (referee)
Bolm`s ligand belongs to the group of 2,2'-bipyridines, which represents a class of C2 symmetric ligands. These ligands form complexes with Lewis acids, which could be used in asymmetric catalysis, for example in the ring-opening of epoxides. Bolm`s ligand analogue was prepared and the enantioselectivity of the ring-opening reaction of cis-stilben oxide with aniline and variety of substituted benzyl alcohols catalyzed by scandium(III) triflate was studied as a part of this bachelor thesis. The enantioselectivity of the reaction using Bolm's ligand analogue was compared to that of Bolm`s ligand. Key words: synthesis, catalysis, bipyridines
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Synthesis of five-membered ring analogues of Amaryllidaceae alkaloids
Kvapilová, Pavlína ; Matoušová, Eliška (advisor) ; Jindřich, Jindřich (referee)
This bachelor Thesis deals with the synthesis of polycyclic compounds containing all-carbon quaternary centres. Quaternary centres with a similar substitution as our target compounds can be found in some natural products. In particular, nitrogen-containing compounds, structurally related to Amaryllidaceae alkaloids, have been prepared in this work. For the construction of the all-carbon quaternary centre we used tandem cyclization/Suzuki cross-coupling and halocarbocyclisation reaction sequence. The first part of the Thesis is dedicated to compounds that have a nitrogen atom protected by a p-methoxybenzenesulfonyl group. In the second part we deal with the preparation of N-methyl derivatives of these compounds. The third part is dedicated to the synthesis of a protected amine from 2-oxazolidinone, which we have unsuccessfully used for the preparation of polycyclic compounds with a hydroxyethyl group on the nitrogen atom. Key words: Synthesis, Amaryllidaceae alkaloids, polycyclic compounds, biological activity
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Synthesis of fluorophores with permanent positive charges for construction of chemosensors on solid phase
Smolka, Ondřej ; Jindřich, Jindřich (advisor) ; Matoušová, Eliška (referee)
This bachelor work is focused on the synthesis of fluorophores with two positive charges based on 1,2,3-triazole motive. The work deals with optimalization of their synthetic processes and characterization of the compounds. Optical properties of the double charged fluorophores and their complexation ability with -cyclodextrin were studied. Key words: 1,2,3-triazoles, charged fluorophores, positive charges, cyclodextrines, complexation
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Preparation of spirocyclic compounds using synergistic catalysis
Rohaľová, Dominika ; Veselý, Jan (advisor) ; Matoušová, Eliška (referee)
Main aim of this diploma work was to develop new method for preparation of spiro compounds based on synergistic catalysis. First part deals with preparation of corresponding starting materials, substituted pyrazol-3-ones and (E)-α,β-unsaturated aldehydes. Second part is focused on cyclization reaction affording spiro compounds and optimization of the conditions (metal and organocatalyst screening, solvent, concentration screening). The last part is the study of scope of the reaction.
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Synthesis of polycyclic compounds containing quaternary carbon centers
Vašíček, Tomáš ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
In this diploma Thesis, a method for the preparation of polycarbocyclic compounds containing all-carbon quaternary centers embedded in triquinane skeleton was prepared. The key reaction sequence leading towards the preparation of these carbocycles was Pd-catalyzed tandem cyclization/Suzuki cross-coupling reaction followed by halocarbocyclization. In the first part of synthetic project, a model oxygen-containing polycyclic derivative was prepared. In the second part, 3 novel polycarbocyclic compounds containing all-carbon quaternary centers were successfully prepared. Synthetic procedure for the starting material required for the key reaction sequence was developed. This approach represents another pathway for the synthesis of polycarbocyclic natural products. Keywords: synthesis, polycyclic compounds, quaternary centers, catalysis
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Enantioselective synthesis of functionalized cyclopentanes
Šotolová, Martina ; Veselý, Jan (advisor) ; Matoušová, Eliška (referee)
This diploma thesis deals with the synthesis of chiral five-membered carbacyclic molecules via iminium-enamine activation using chiral secondary amines. The first part of thi diploma thesis describes the synthesis of starting materials for domino Michael addition/α-alkylation reaction, i.e. the synthesis of α,β-unsaturated aldehydes and 1-bromo-3-nitropropane. The second part of this diploma thesis is focused on the optimization of reaction conditions and the application of the domino Michael addition/α-alkylation reaction, that leads to the formation of cyclopentancarbaldehydes with contiguous stereogenic centres. Key words Asymmetric synthesis, organocatalysis, domino reaction, Michael addition, cyclopentanes.
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Stereoselective synthesis of spiro compounds containing cyclohexenecarboxylic acid
Dočekal, Vojtěch ; Veselý, Jan (advisor) ; Matoušová, Eliška (referee)
This bachelor thesis is focused on stereoselective preparation of spiro compounds using organocatalytic approach and their transformation to substrates with potential biological activity. First part of this work deals with stereoselective synthesis of spiro compounds using heterocyclic enals and sulphur-containing nucleophile. These organocatalytic reactions were catalysed by chiral secondary amine utilizing tandem Michael/Michael/aldol reaction. Second part of this work is focused on transformation of prepared unsaturated heterocyclic spiro aldehydes to corresponding carboxylic acids, which will be studied for their possible biological activity. Key words Enantiomer, diastreomer, stereoselective synthesis, organocatalysis, Michael addition, aldol condensation, Wittig reaction, Pinnick oxidation.
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Reaction intermediates in homogeneous gold catalysis
Shcherbachenko, Elena ; Roithová, Jana (advisor) ; Matoušová, Eliška (referee)
The presented master thesis is devoted to the investigation of reaction intermediates in homogeneous gold catalysis. Electrospray ionization mass spectrometry (ESI-MS) was used as the primary research technique in this study. Delayed reactant labeling was used as the main method. I have focused mainly on the hydration of 1-phenyl-1-propyne catalyzed by the gold complex [Au(IPr)(MeCN)]BF4 (IPr = 1,3-bis(2,6-di-iso-propylphenyl)imidazol-2- ylidene). I have detected two main intermediates containing one or two gold atoms, respectively (monoaurated and diaurated intermediate). I have obtained rate constants for the degradation of the reaction intermediates and their half-lives. I have derived kinetic isotope effects for the formation and the decomposition of the detected intermediates. I have shown that the kinetics of the degradation of both intermediates is identical, therefore I conclude that hydration of alkynes catalyzed by gold complex [Au(IPr)(MeCN)]BF4 proceeds most probably via neutral monoaurated intermediates. These neutral intermediates are detected by ESI-MS as protonated (monoaurated intermediate) or tagged by a second gold cation (diaurated intermediate). Key words: gold catalysis, reaction intermediates, electrospray ionization, mass spectrometry.
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Cyclization Reactions Mediated by Transition Metals
Matoušová, Eliška ; Pour, Milan (advisor) ; Bureš, Filip (referee) ; Šrogl, Jiří (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of inorganic and organic chemistry Candidate: Mgr. Eliška Matoušová Supervisor: prof. RNDr. Milan Pour, PhD. Title of Doctoral Thesis: Cyclization reactions mediated by transition metals Within the framework of this Thesis, several analogues of naturally occurring biologically active pyranones were prepared. The synthetic procedure was based on a Pd-cata- lyzed carbopalladation of enyne precursors with subsequent lactonization. Employing this method, bicyclic pentenolides containing fused nitrogen heterocycle as well as carbocycle were synthesized. The preparation of the corresponding oxygen-containing derivative was not successful. The compounds were tested for their antifungal, anitibacterial and cytostatic activity. The second part of the Thesis deals with synthesis of furans and dihydropyrans via palladium and gold catalysis. A highly efficient method for AuI -catalyzed cyclization of propargyl vinyl ethers to dihydropyrans was developed using tris(2-furyl)phosphine as a ligand and methanol as a nucleophile. This method was employed for the preparation of 15 dihydropyran derivatives in high yields. In the absence of a nucleophile furans were formed in lower yields. Dihydropyrans undergo an as yet undescribed...
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The synthesis of the derivatives of 2-aryl-4-methylcyclopent-2-en-1-one with potential antifungal activity
Matoušová, Eliška ; Kuneš, Jiří (advisor) ; Hrabálek, Alexandr (referee)
THE SYNTHESIS OF THE DERIVATIVES OF 2-ARYL-4-METHYLCYKLOPENT-2-EN-1-ONE WITH POTENTIAL ANTIFUNGAL ACTIVITY Eliška Matoušová ABSTRACT Several series of compounds with potential antifungal activity related to a national product incrustoporine have been synthesized in last years. The aim of this thesis was to prepare the set of carbanalogues of incrustoporine (2-arylderivatives of 4-methylcyklopent-2-en-1-one) to find whether the substitution of oxygen atom in lactone group by methylen would have any influence on the activity. We found that the antifungal effect of these compounds was very low. It means that the lactone group is necessary for the activity. All the compounds was also tested for cytotoxic activity but they did not display any significant effect. Z O 2-subst.phenyl-4-methylcyklopent-2-en-1-one O O (-) incrustoporine
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