magistrsko delo
Maša Kastner (Author), Bogdan Štefane (Mentor), Jurij Lah (Thesis defence commission member), Uroš Grošelj (Thesis defence commission member)

Abstract

Tvorba novih C–C vezi je v kemiji pomembna za pripravo strukturno kompleksnih produktov. Zelo eleganten pristop za tvorbo novih ogljik-ogljik vezi je preko neposredne C–H aktivacije. C–H funkcionalizacija nam je omogočila doseg regioselektivnosti, saj imajo naši substituirani kinazolini bogata reaktivna mesta. Kinazolini so pogosto gradnik v naravnih virih, kot tudi farmacevtskih učinkovinah in imajo širok spekter bioloških lastnosti, zato so zanimivi za raziskovanje. V magistrskem delu smo preučevali direktno rutenij/paladij dvojno C–H ariliranje 2-substituiranih kinazolinov 6. Raziskovali in optimizirali smo tako prvo rutenij(II)-katalizirano, kot tudi paladij(II)-katalizairano stopnjo reakcije. V primeru obeh s kovino kataliziranih reakcij smo preverili vpliv različnih katalizatorjev, medija, baze, liganda, aditiva, temperature, ter količine dodanih reagentov. S končnimi optimiziranimi pogoji rutenij-katalizirane stopnje smo sintetizirali, očistili in okaraktezirali monoarilirane produkte 10 v primeru tiofenskega, kot tudi furanskega kinazolinskega derivata z dobrimi izkoristki (23–67 %). Najboljši pogoji paladij-katalizirane stopnje pa so nam prav tako omogočili sintezo, s sledečim čiščenjem in karakterizacijo končnih diariliranih produktov 14 (26–52 %). V zadnjem delu smo preverili tudi uspešnost »one-pot« metode, brez vmesne izolacije intermediata. Izkazala se je za enako primerno in enostavnejšo sintezno pot, saj smo dosegli primerljive izkoristke izvedenih reakcij.

Keywords

organske reakcije;C-H aktivacija;funkcionalizacija;substituirani kinazolini;'one-pot' metoda;kataliza;rutenij;paladij;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [M. Kastner]
UDC: 547.831:66.095.257(043.2)
COBISS: 20947203 Link will open in a new window
Views: 709
Downloads: 207
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Other data

Secondary language: English
Secondary title: Ruthenium/palladium sequential arylation of heteroaryl quinazoline derivatives
Secondary abstract: The formation of new C–C bonds is important in chemistry for the preparation of structurally complex products. A very elegant approach for the formation of new carbon-carbon bonds is through direct C–H activation. C–H functionalization allowed us to reach regioselectivity, since our substituted quinazolines have abundant reactive sites. Quinazolines are often a building block in natural sources as well as pharmaceutical substances and have a wide range of biological properties, which is why they are interesting for further exploration. In the master’s thesis we studied directed ruthenium/palladium double CH arylation of 2-substituted quinazolines 6. Both ruthenium(II)- and palladium(II)-catalysed reaction rates were investigated and optimized. in both metal-catalysed reaction steps, the effect of different catalysts, medium, base, ligand, additive, temperature, and the amount of reagents used were checked. With the final optimized reaction conditions of the ruthenium-catalysed step, the monoarylated products 10 were synthesized, purified and characterized in the case of the thiophene as well as the furan derivative in good yields (23-67%). The best conditions of the palladium-catalysed step also allowed us to synthesize, with subsequent purification and characterization of the final diarylated products 14 (26-52%). In the last part, we also checked the performance of the one-pot method, without the need to isolate the intermediate. It proved to be an equally appropriate and simpler synthesis protocol, as we achieved comparable yields of the performed reactions.
Secondary keywords: C-H activation;functionalisation;substituted quinazolines;'one-pot' method;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages: 98 str.
ID: 11868137