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S paladijem katalizirano aminiranje 2-bromonaftalenskih derivatov
ID Topić, Tanja (Author), ID Košmrlj, Janez (Mentor) More about this mentor... This link opens in a new window

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Abstract
V tem magistrskem delu smo želeli zasnovati učinkovit sintezni pristop k aminiranju izbranih naftalenskih derivatov. Namen je bil priprava manjše knjižnice aminskih derivatov, ki bi bili potencialno uporabni kot molekulske sonde za ex vivo detekcijo bioloških označevalcev Alzheimerjeve bolezni. Načrtovane spojine so ustrezale 'push-pull' strukturi (donor–π-vmesnik–akceptor) z različnimi donorji. Kot donorje smo izbrali nekatere ciklične alifatske amine, pri katerih je rotacija med donorskim delom in π-vmesnikom sterično ovirana, kar vpliva na optične lastnosti. Za sintezo smo raziskali možnosti aminiranja π-vmesnika v pozni fazi sinteze z uporabo Buchwald-Hartwigovega spajanja. V modelni reakciji smo uporabili substrat z bazično občutljivim fragmentom, 4-metil-2-okso-2H-piran-3-karbonitrilno skupino. Ugotovili smo, da amin v večjem prebitku z njim reagira. Uspelo nam je pripraviti 4-metil-6-(6-(pirolidin-1-il)naftalen-2-il)-2-okso-2H-piran-3-karbonitril, ki smo ga okarakterizirali z $^1$H in $^{13}$C NMR spektroskopijo.

Language:Slovenian
Keywords:sinteza, spajanje, amin, Buchwald-Hartwig
Work type:Master's thesis/paper
Typology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2024
PID:20.500.12556/RUL-163055 This link opens in a new window
COBISS.SI-ID:217828099 This link opens in a new window
Publication date in RUL:01.10.2024
Views:637
Downloads:313
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Secondary language

Language:English
Title:Palladium-catalysed amination of 2-bromonaphthalene derivatives
Abstract:
In this thesis, we aspired to develop an efficient synthetic approach for the amination of selected naphthalene derivatives. Our goal was to prepare a small library of amine derivatives with potential as molecular probes for ex vivo detection of Alzheimer's disease biomarkers. The synthesized compounds featured a 'push-pull’ structure (donor-π-acceptor), with variations in the donor group. We chose cyclic aliphatic amines as donors due to their inherent steric hindrance, which restricts its rotation and, consequently, influences their optical properties. We investigated late-stage amination of the π-linker using Buchwald-Hartwig reaction conditions. In a model reaction, we utilized a substrate containing a base-labile 4-methyl-2-oxo-2H-pyran-3-carbonitrile moiety. Our findings indicated that a higher excess of amine reacts with the substrate. We synthesized 6-(6-(pyrrolidin-1-yl)naphthalene-2-yl)-4-methyl-2-oxo-2H-pyran-3-carbonitrile, which was characterized by $^1$H and $^{13}$C NMR spectroscopy.

Keywords:synthesis, cross-coupling, amine, Buchwald-Hartwig

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