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The Combination of Organometallic, Transition-Metal Catalyzed, Radical and Carbocationic Reaction Steps to Domino Processes
Jagtap, Pratap Ramling ; Jahn, Ullrich (advisor) ; Tobrman, Tomáš (referee) ; Bureš, Filip (referee)
This work deals with the development of methodology, which couples reactive intermediates of varying oxidation states, in tandem sequences comprising 1,2-organometallic addition/transition metal catalyzed isomerization/Michael addition/SET oxidation/radical cyclization/oxygenation steps in the synthesis of highly functionalized carbocycles. Implementation of this sequence being catalytic in the SET oxidant was studied. 1,4-Diketones were synthesized in a tandem 1,2-addition/ruthenium-catalyzed redox isomerization/enolates oxidation/radical dimerization reaction and results were compared with 1,4-diketones formation via oxidative coupling of ketone enolates. The total synthesis of selective tetrahydrofuran lignans from 1,4-diketones obtained in a tandem addition/isomerization/dimerization reaction is also documented
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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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