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Development of New Syntheses of Azaaromatic Compounds with Extended π-System
Ulč, Jan ; Kotora, Martin (advisor) ; Hrdina, Radim (referee) ; Tobrman, Tomáš (referee)
Azapolyaromatic compound are a class of heterocyclic compounds, which contains at least one nitrogen atom. A subclass of these compounds are quinolizinium salts, which contains nitrogen atom in bridgehead position. These salts usually have interesting photophysical properties. Naphthoquinolizinium salts are a group of quinolizinium salts, but their synthesis as well as their photophysical properties haven't been studied in detail yet. This work is about development of a new modular method for preparation of naphthoquinoliziniu salts. This method is based on catalytic C-C and C-H bond activations by transition metal catalysts. 1-Azabiphenylene was used as a starting material, which reacted in catalytic C-C bond cleavage followed by insertion of various alkyne to form benzo[h]quinolines. These benzo[h]quinolines then reacted in catalytic C-H bond activation reaction followed by insertion of another alkyne to form final tetrasubstituted naphthoquinolizinium salts. Photophysical properties of the prepared salts was studied. The developed method was used on a more complex starting material such as linear 1- 1-aza-[3]triphenylene, which was converted to phenanthroquinolines and eventually to the corresponding azonia salts. Key words: azapolyaromatic compounds, catalysis by transition metal complexes, C-C...
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Catalytic Cycloaddition Reactions of Tribenzocyclyne
Jacko, Jaroslav ; Kotora, Martin (advisor) ; Schulz, Jiří (referee)
The main aim of the bachelor thesis was to investigate the reactivity of tribenzocyclyne, a triangular molecule, undergoing reactions with antiaromatic biphenylenes and their heteroanalogues. Those reactions consist of C-C activations of strained bond mediated by the complexes of the group 9 elements, followed by migratory insertion of present alkyne which leads to the formation of a substituted aromatic ring. Presented method facilitated the setting of a experiment as well as cutting down on reaction steps. These investigations will subsequently serve for further progress in the chemistry of cyclic hexa- ortho-phenylenes. Key words: catalysis, cycloaddition, tribenzocyclyne, the C-C bond cleavage
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