20.500.12556/RUL-172072 Poskus selektivnega devteriranja nekaterih heteroaril karboksamidov Toward selective deuteration of some heteroaryl carboxamides Selektivno devteriranje N-heterocikličnih aromatov je pomembno za farmacevtske namene in za študije mehanizmov kemijskih reakcij. V okviru diplomskega dela smo iz karboksilnih kislin diazinov sintetizirali šest karboksamidov. Pripravljene amide smo poskušali devterirati z uporabo usmerjenega orto-metaliranja. To smo dosegli z litijevim 2,2,6,6-tetrametilpiperididom ter težko vodo, kot cenovno ugodnim, varnim in okolju prijaznim virom devterija. Po optimizaciji protokola smo štiri substrate uspešno in selektivno devterirali z visoko uvedbo devterija, medtem ko se je en substrat devteriral z nižjo regioselektivnostjo. Poleg devteriranih spojin smo kot stranske produkte metaliranja izolirali dimere začetnih amidov. Preučili smo vpliv različnih dejavnikov na učinkovitost devteriranja in tvorbo dimerov. Naša metoda se odlikuje po uporabi težke vode kot vira devterija ter enostavnih reagentov brez dragocenih kovin, ki se klasično uporabljajo za tovrstne procese. Sintetizirane izotopsko označene amide bi bilo mogoče v prihodnosti nadalje uporabiti za sintezo devteriranih molekul z visoko dodano vrednostjo. Selective deuteration of N-heterocyclic aromatics is important for pharmaceutical purposes and for studying reaction mechanisms. As part of this thesis, six carboxamides were synthesized from diazine carboxylic acids. The synthesized amides were subjected to deuteration using directed ortho-metalation. This was achieved using lithium 2,2,6,6 tetramethylpiperidide and employing heavy water as an inexpensive, safe, and environmentally friendly deuterium source. After optimizing the protocol, four substrates were selectively deuterated with high deuterium incorporation, while one substrate exhibited lower regioselectivity. In addition to the deuterated compounds, we isolated dimers of the starting amides as side products of the metalation. Several factors influencing the efficiency of deuteration and dimer formation were investigated. Our method stands out by using heavy water as the deuterium source and simple reagents, avoiding the precious metals typically used in such processes. The synthesized isotopically labelled amides could be further transformed and used in the syntheses of high-value deuterated molecules in the future. devterij heteroaromatske molekule izotopsko označevanje usmerjeno orto-metaliranje deuterium heteroaromatic molecules isotope labelling directed ortho-metalation true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2025-09-05 09:25:01 2025-09-05 09:25:05 2025-10-22 09:16:07 0000-00-00 00:00:00 2025 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 25365 254205187 Birk_Jernej_-_Poskus_selektivnega_devteriranja_nekaterih_heteroaril_karboksamidov.pdf Birk_Jernej_-_Poskus_selektivnega_devteriranja_nekaterih_heteroaril_karboksamidov.pdf 1 47FB02D3E9B1942D25560FA5E318B5E0 4c4943f297911475b498407dbb296646e4885cd5d9104fff3e8ae12a94d90d73 4b43aa5c-8a29-11f0-9328-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=215798 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0