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Pretvorbe izbranih derivatov 2-bromonaftalena
ID Oražem, Žiga (Author), ID Košmrlj, Janez (Mentor) More about this mentor... This link opens in a new window

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Abstract
V sklopu te diplomske naloge smo želeli sintetizirati tri naftalenske derivate, ki jih lahko uporabljamo za nadaljnjo sintezo. Produkti se lahko uporabljajo kot substrati za grajenje večjih molekul, za sintezo nekaterih zdravil in barvil, lahko pa jih tudi povežemo med seboj v molekulsko sondo, ki bi se lahko potencialno uporabljala kot sredstvo za zgodnje določanje Alzheimerjeve bolezni. Želene produkte smo poskusili sintetizirati iz 2-bromonaftalena oziroma njegovih derivatov. Uspešno smo sintetizirali dva vmesna produkta (6-bromo-N,N-dimetilnaftalen-2-amin in 1-(6-hidroksinaftalen-2-il)etan-1-on) ter en končni produkt (1-(6-bromonaftalen-2-il)etan-1-on) s sprejemljivimi izkoristki, vse pa smo očistili in jih okarakterizirali z 1H NMR, 13C NMR, IR in HRMS spektrometrijo ter preverili njihovo čistost s HPLC analizo. Ker so bili vsi ti produkti trdni, smo jim uspeli izmeriti tudi tališča.

Language:Slovenian
Keywords:2-bromonaftalen, 2, 6-disubstituirani naftaleni, Bucherer reakcija, spajanje po Hecku, (6-(dimetilamino)naftalen-2-il)borova kislina, 1-(6-bromonaftalen-2-il)etan-1-on.
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2022
PID:20.500.12556/RUL-139480 This link opens in a new window
COBISS.SI-ID:125103619 This link opens in a new window
Publication date in RUL:02.09.2022
Views:740
Downloads:77
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Secondary language

Language:English
Title:Transformations of selected 2-bromonaphthalene derivatives
Abstract:
As a part of this Bachelor's thesis we tried to synthesize three derivatives of naphtalene, which can be used as a substrate for further synthetic purposes. The products can be used as a substrate for building larger molecules, the production of some medicines and dyes, but they can be also coupled into a molecular probe that can be potentially used for early determination of Alzheimer's disease. We tried to synthesize the desired molecules from 2-bromonaphtalene or its derivatives. We have succesfully synthesized two intermediate products (6-bromo-N,N-dimethylnaphtalen-2-amine and 1-(6-hydroxynaphtalen-2-yl)ethan-1-one) along with one target compound (1-(6-bromonaphtalen-2-yl)ethan-1-one) with acceptable yields. All of these products were purified and characterized using 1H NMR, 13C NMR, IR and HRMS spectrometry and their purity was determined with HPLC analysis. Because the obtained products were solid, we were also able to determine their melting points.

Keywords:-bromonaphtalene, 2, 6-disubstituated naphtalenes, Bucherer reaction, Heck cross-coupling, (6-(dimethylamino)-2-naphtalenyl)boronic acid, 1-(6-bromo-2-naphtalenyl)ethane-1-one.

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