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 1H and 13C NMR spectroscopy.
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