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Using N-hydroxysuccinimidyl formate as a CO source in tandem reactions
Bahramian, Artur ; Matoušová, Eliška (advisor) ; Smrček, Stanislav (referee)
This bachelor thesis deals with the use of N-hydroxysuccinimidyl formate as a source of CO in tandem reactions. The prepared starting materials were used in a tandem reaction involving cyclic carbopalladation, carbonylation and cross-coupling. The first part of the thesis describes the synthesis of starting material with a six-membered ring and of the selected CO surrogate. These compounds were subjected to a tandem reaction to form a product with a carbonyl group. Furthermore, the reaction conditions were studied and then the efficiency of using the selected formate compared to the gaseous carbon monoxide was compared. Keywords: synthesis, tandem reaction, cross-coupling, N-hydroxysuccinimidyl formate, carbon monoxide
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Using tandem cyclisation/Sonogashira cross-coupling in the synthesis of natural products and their derivatives
Liška, Benno ; Matoušová, Eliška (advisor) ; Míšek, Jiří (referee)
The subject of this bachelor's thesis is the preparation of polycyclic compounds using the tandem cyclisation/Sonogashira cross-coupling and a potential application of this reaction to the synthesis of natural products and their derivatives. The aim was to study this method using nonaromatic starting materials with a six-membered ring and to explore possibilities for functionalisation of the triple bond of the newly prepared compounds. The first part of this thesis deals with the synthesis of starting materials containing either an ether group or a malonate residue. The second part deals with the optimisation of conditions and the investigation of the scope of Heck reaction and Sonogashira cross-coupling. The third part describes the attempts to hydrate the triple bond and the last part contains reactions with allylic alcohols. Keywords: synthesis, tandem reaction, natural products, Sonogashira cross-coupling, Heck reaction
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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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