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O-Karbamat kot usmerjajoča skupina za pripravo devteriranih heteroaromatskih spojin
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 magistrskega dela smo pripravili serijo (hetero)aromatskih O-karbamatov iz pripadajočih hidroksi(hetero)aromatov. V naboru spojin smo raziskovali sintezo O-karbamatov z elektronsko-bogatimi obroči, kot tudi z elektronsko-revnimi. Sintetizirane heteroaromatske O-karbamate smo poskušali izotopsko označiti z devterijem z uporabo litijevih baz in D$_2$O, kot virom devterija, pri čemer smo uporabili karbamatno skupino kot usmerjajočo skupino za orto-devteriranje. Ugotovili smo, da večino substratov lahko uspešno in selektivno izotopsko označimo. Metodo devteriranja smo prenesli na večjo organsko spojino, ki predstavlja vmesno stopnjo pri sintezi protirakave učinkovine momelotinib, katero smo tudi uspešno izotopsko označili.

Language:Slovenian
Keywords:O-Karbamat, usmerjajoča skupina, heteroaromatsk spojine, izotopsko označevanje, momelotinib
Work type:Master's thesis/paper
Typology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2025
PID:20.500.12556/RUL-169455 This link opens in a new window
COBISS.SI-ID:237674499 This link opens in a new window
Publication date in RUL:29.05.2025
Views:319
Downloads:70
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Secondary language

Language:English
Title:O-Carbamate as a directing group for the preparation of deuterated heteroaromatic coumpounds
Abstract:
In the scope of this Master's thesis, a range of (hetero)aromatic O-carbamates were prepared from their corresponding hydroxy(hetero)aromatics. O-Carbamates of electron-rich and electron-deficient systems were synthesised. These compounds were isotopically labelled with the use of lithium bases and D$_2$O as a source of deuterium. In this step, the carbamate group functioned as a directing group for ortho-deuteration. It was found that most of the starting O-carbamates were successfully labelled under these conditions. The deuteration was also successfully performed on a larger molecule, which represents an intermediate in the synthesis of the anti-cancer drug momelotinib.

Keywords:O-Carbamate, directing group, heteroaromatic compounds, isotope labelling, momelotinib

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