20.500.12556/RUL-163055 S paladijem katalizirano aminiranje 2-bromonaftalenskih derivatov Palladium-catalysed amination of 2-bromonaphthalene derivatives 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. 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. sinteza spajanje amin Buchwald-Hartwig synthesis cross-coupling amine Buchwald-Hartwig true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2024-10-01 14:45:00 2024-10-01 14:45:08 2024-12-05 12:24:05 0000-00-00 00:00:00 2024 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 22979 217828099 Topic_Tanja_-_Poskusi_s_paladijem_kataliziranega_aminiranja_2-bromonaftalenskih_derivatov.pdf Topic_Tanja_-_Poskusi_s_paladijem_kataliziranega_aminiranja_2-bromonaftalenskih_derivatov.pdf 1 43865BC3FBF8158E7ED952AFBE69D3C4 5748aacf31677b8d6b7b8a8775b6a3b36dcb108d358fcef489be7cb0fdb93433 d803dd43-7ff2-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=192525 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0