20.500.12556/RUL-130158 Sinteza in pretvorbe 4-benziliden-2-feniloksazolonov Synthesis and transformations of 4-benzylidene-2-phenyloxazolones Oksazoloni so zaradi svoje reaktivnosti odlični izhodni substrati za odkrivanje sinteznih poti za nove heterociklične in aminokislinske produkte. Iz hipurne kisline in 2-bromobenzaldehida, v prisotnosti acetanhidrida in kalijevega acetata, sem po Erlenmeyer azlakton postopku sintetiziral 4-(2-bromobenziliden)-2-feniloksazolon. Produkt sem z dodatkom trietilamina v metanolu pretvoril do metil 2-N-benzamido-3-(2-bromofenil)akrilata. Za zaključek sem izvedel še hidrogeniranje akrilata, raztopljenega v metanolu, s 10 mol% katalizatorja tris(trifenilfosfin)rutenijev (II) diklorid in dobil končni produkt metil 2-N-benzamido-3-(2-bromofenil)propanoat. Ugotovil sem, da je celotna sintezna pot zadosti ponovljiva, ter ima dobre izkoristke na vseh sinteznih korakih. Due to their reactivity, oxazolones make excellent starting substrates in diversity oriented synthesis for discovering new synthetic pathways for the formation of amino acid and heterocyclic products. Using the Erlenmeyer azlactone synthesis, I synthesized 4-(2-bromobenzylidene)-2-phenyloxazolone, using hippuric acid and 2-bromobenzaldehyde as starting substrates in the presence of acetic anhydride and potassium acetate. I converted the product to methyl 2-N-benzamido-3-(2-bromophenyl) acrylate by adding triethylamine in methanol. I finished the process with the hydrogenation of the obtained acrylate in methanol with 10 mol% of the catalyst tris(triphenylphosphine)ruthenium(II) dichloride. The final product was methyl 2-N-benzamido-3-(2-bromophenyl) propanoate. I found the method of synthesis to be sufficiently repeatable, and has good efficiencies at all steps. oksazolon heterocikel hidrogeniranje oxazolone heterocycle hydrogenation true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2021-09-10 13:40:00 2021-09-10 13:40:03 2022-09-09 04:15:04 0000-00-00 00:00:00 2021 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 16441 84650755 Muhic_Jakob_-_Sinteza_in_pretvorbe_4-benziliden-2-feniloksazolonov.pdf Muhic_Jakob_-_Sinteza_in_pretvorbe_4-benziliden-2-feniloksazolonov.pdf 1 9A7039E3C74279D7F964377888EEABAA 9eb81066ce1933b6ce34105bb4895cbf3d8836cf5788f3af8f07bfaddd93593a 96c41412-122b-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=147217 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0