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Synthesis of 4-alkylidenepyrazolones and their use in preparation of spirocycles
Boudová, Hana ; Veselý, Jan (advisor) ; Matoušová, Eliška (referee)
Due to the wide use of spirocyclic compounds containing heterocycles, especially in medicinal chemistry, this bachelor thesis deals with the preparation of 4-alkylidenepyrazolones and their use to prepare pyrazolone-derived spirocyclic compounds using organocatalysis with tertiary amines. 4-Alkylidenepyrazolones were prepared by Knoevenagel condensation of pyrazolones and aldehydes, the preparation of spiropyrazolones was carried out by the cyclization reaction of 3-nitropropyl-mesylate with suitable 4-alkylidenepyrazolone derivatives. Key words 4-alkylidenpyrazolones, α,β-unsaturated pyrazolones, Knoevenagel reaction, 3-nitropropyl-mesylate, spirocyclic compounds, spiropyrazolones, organocatalysis
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Synthesis of analogues of natural alkaloids containing quaternary carbon centres
Sádková, Michaela ; Matoušová, Eliška (advisor) ; Baszczyňski, Ondřej (referee)
This bachelor thesis is concerned with organic synthesis of polycyclic compounds containing quarternary carbon centres, which are structurally similar to Amaryllidaceae and Sceletium alkaloids. The aim of this work was to prepare compounds suitable for biological activity screening. To obtain the quarternary carbon centre, two key steps were used - tandem cyclisation/Suzuki cross-coupling and halocarbocyclisation. The first part of this work is focused on the synthesis of starting materials with two types of silyl groups. The second part deals with the preparation of quarternary carbon centre using tandem cyclisation/Suzuki cross-coupling and halocarbocyclisation. In the last part, experiments to form a double bond are described, together with its derivatisation to synthesise compounds with a potential biological activity. Key words: synthesis, alkaloids, Amaryllidaceae, Sceletium, polycyclic compounds, quarternary carbon centres
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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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Use of alkenylboronic acids in the tandem cyclisation/Suzuki cross-coupling
Klanicová, Kristýna ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
This thesis deals with the synthesis of polycyclic compounds using tandem cyclisation/Suzuki cross-coupling, by modification of the method developed by our research group. This thesis mainly investigates the scope of the tandem reaction with aliphatic boronic acids or their esters. The products of the palladium catalyzed reaction then underwent electrocyclization to form an aromatic ring. The polycyclic skeleton, containing the aromatic core, is found in a considerable amount of natural substances with biological activity. The structure of the compounds prepared herein is similar to miltiorin D or commiphorane A.
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Catalytic annulation reactions of N-heterocycles with alkynes
Hrubý, Samuel ; Kotora, Martin (advisor) ; Matoušová, Eliška (referee)
The aim of the bachelor thesis was to use C-C and C-H bond cleavage for the synthesis of cationic N-heterocycle compounds. Within the thesis was the aim to study various catalytic systems, reactions considering structural variations of reactants along with the effect of structure of reactants on their reactivity. The synthesis consists of rhodium-catalysed C-C bond cleavage in biphenylene followed C-H activation. Key words: C-C bond activation, C-H bond activation, heterocycles, catalysis
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Using Heck reaction for aromatic ring formation in the synthesis of polycyclic compounds
Bažíková, Ema ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
This bachelor's thesis focuses on the synthesis of a polycarbocyclic compound with naphthalene core and the following oxidation to the corresponding ortho-naphthoquinone. The naphthalene and naphthoquinone skeleton can be found in many natural products with interesting biological properties. This thesis extends the scope of a method developed by our group for the synthesis of naturally occurring ortho-naphthoquinones. The key step of the synthesis was to form an aromatic ring using the Heck reaction. Keywords: synthesis, polycyclic compounds, naphthalenes, catalysis, Heck reaction
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Using levoglucosenone in the synthesis of naphthoquinone containing compounds
Neumannová, Johana ; Matoušová, Eliška (advisor) ; Baszczyňski, Ondřej (referee)
This bachelor thesis is focused on using levoglucosenone in the synthesis of the naphthoquinone containing compounds. Levoglucosenone is a versatile and easily available substance which can be prepared by pyrolysis of renewable cellulose-containing materials. The synthesis of the target compound begins with the preparation of the substrate for the tandem reaction (propargyl ether) in three steps. The following key steps of the synthesis include palladium-catalyzed tandem cyclization/Suzuki cross coupling and subsequent Heck reaction. Oxidation of the prepared methoxy-substituted naphthalene yields the o-naphthoquinone, which has a similar structure as some naturally occurring substances with naphthoquinone skeleton, e.g. mansonone D and populene C. Key words: Synthesis, naphthalenes, naphthoquinones, levoglucosenone, catalysis, polycyclic compounds
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Synthesis of all-carbon quaternary centres
Orlovská, Ľubica ; Matoušová, Eliška (advisor) ; Hájíček, Josef (referee)
In this diploma Thesis I dealt with the synthesis of nitrogen compounds that contain quaternary carbon centres and their structure resembles natural substances, specifically alkaloids from the Amaryllidaceae family. Halocarbocyclization or Heck reaction was planned as a key step of the synthesis, which should lead to the formation of quaternary carbon centres. First, starting nitriles and esters with five- and six-membered rings were prepared. Subsequently, the method for the preparation of a stable bicyclic ketone with a five-membered ring from an ester was optimized. The next part of the Thesis is devoted to the synthesis of a substrate for the Heck reaction from the prepared ketone, which was then used for the preparation of the alkaloid skeleton with a quaternary carbon centre, unfortunately without success so far. In the last part of the work, a bicyclic ketone with a six-membered ring, from which it is possible to prepare a substrate for the Heck reaction in several steps already used for five-membered substances, was prepared from the nitrile by carbopalladation. Key words: synthesis, quaternary carbon centres, Heck reaction, halocarbocyclisation, Amaryllidaceae alkaloids
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Application of enantioselective allylation for synthesis of compounds isolated from Streptomyces gramineus
Morávková, Terézia ; Kotora, Martin (advisor) ; Matoušová, Eliška (referee)
E-492, actinofuranone A, and JBIR-108 are natural compounds isolated from actinobacteria Streptomyces genus and can lead to the development of new pharmaceuticals as they have some biological interesting activities. Although the synthesis of these actinofuranones has been already published, this work brings new methods for the preparation of their fragments. The key step of the synthesis is enantioselective crotylboration of an aldehyde catalyzed by a chiral Brønsted acid and by which two centres of chirality are introduced in one step. The other crucial steps of the synthesis are composed of Ru-catalyzed alkene-alkene cross-metathesis and Pd- catalyzed Suzuki cross-coupling. Keywords: natural compound, enantioselective syntheses, crotylation, catalysis, actinofuranone fragment
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The use of alkylideneheterocycles for the synthesis of spirocyclic compounds
Vopálenská, Andrea ; Veselý, Jan (advisor) ; Matoušová, Eliška (referee)
This bachelor thesis is focused on the stereoselective Michael-alkylation reaction of alkylidene heterocycles using bifunctional organocatalysis. Within the thesis, suitable starting materials were first prepared and then the organocatalytic reaction leading to the formation of spirocyclic compounds was optimized. Under optimized conditions, a study of the scope of application of the method on selected derivatives was also performed and the optical purity of the products was determined. Key words Organocatalysis, asymmetric synthesis, cascade reaction, Michael reaction, bifunctional organocatalysts, spirocyclic compounds
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