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Rutenij/paladij dvojno ariliranje heteroaril kinazolinskih derivatov
Kastner, Maša (Author), Štefane, Bogdan (Mentor) More about this mentor... This link opens in a new window

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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.

Language:Slovenian
Keywords:C–H aktivacija, funkcionalizacija, substituirani kinazolini, »one-pot« metoda
Work type:Master's thesis/paper (mb22)
Tipology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
COBISS.SI-ID:20947203 Link is opened in a new window
Views:159
Downloads:76
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Secondary language

Language:English
Title:Ruthenium/palladium sequential arylation of heteroaryl quinazoline derivatives
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.

Keywords:C–H activation, functionalisation, substituted quinazolines, »one-pot« method.

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