20.500.12556/RUL-129227 Sinteza imobilizirane 4-aminobenzojske kisline in njena uporaba v pripravi imobiliziranih Cu(II)-enaminon katalizatorjev Synthesis of immobilised 4-aminobenzoic acid and its use in preparation of immobilised Cu(II)-enaminone catalysts V tem diplomskem delu sem raziskoval imobilizirane baker enaminon katalizatorje, vezane na aminopropil silikagel, kjer je 4-aminobenzojska kislina služila kot povezava med silikagelom in enaminonom. Uspešno sem s funkcionaliziranega silikagela 1 in 1' s hidroksilaminom odcepil enaminon, da sem pridobil imobilizirano 4-aminobenzojsko kislino s prostim aminskim fragmentom 2, kar sem potrdil z IR spektroskopijo. Ta reakcija poteka tako, da hidroksilamin povzroči ciklizacijo enaminona, kar povzroči njegov odcep od nosilca. Strukturo heterocikličnega stranskega produkta sem dokazal z NMR spektroskopijo. Na prosto aminsko skupino sem želel vezati nov enaminon, da bi nastali novi imobilizirani enaminoni 4a–c, a ta reakcija ni bila uspešna niti pod ostrejšimi pogoji. Zato sem na izhodno spojino 1 koordiniral Cu(II) ione, da sem pridobil katalizator 5. Nastali katalizator sem uporabil v modelni reakciji za sintezo bicikličnega pirazolidinona, metil 6,7-dihidro-7,7-dimetil-1-(3,4,5-trimetoksifenil)-5-okso-1H,5H-pirazolo[1,2-a]pirazol-2-karboksilata (9). Njegov nastanek in učinkovitost katalizatorja sem dokazal z NMR spektroskopijo. In this diploma thesis, I have researched immobilised copper-enaminone catalyst, bound onto aminopropyl silica gel, where 4-aminobenzoic acid served as a linker between the silica gel and the enaminone. The enaminone was successfully removed from 1 and 1' with hydroxylamine hydrochloride to give immobilised 4-aminobenzoic acid with a free amino group 2, which was confirmed using IR spectroscopy. This reaction takes place, via cyclisation of hydroxylamine with enaminone, which cleaves from the silica gel. The structure of heterocyclic by-product of this reaction was confirmed using NMR spectroscopy. The binding of new enaminones onto the 'free' amine group was then considered to gain new products 4a–c, but the reactions proved unsuccessful even under harsher conditions. Because of that, copper was coordinated onto starting material 1 to gain the catalyst 5. The prepared catalyst was then tested on a model reaction for the synthesis of bicyclic pyrazolidinone, methyl 6,7-dihydro-7,7-dimethyl-1-(3,4,5-trimethoxyphenyl)-5-oxo-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylate (9). The full conversion with this catalyst was confirmed by NMR spectroscopy. 4-aminobenzojska kislina enaminon bakrov katalizator biciklični pirazolidinoni 4-aminobenzoic acid enaminone copper catalyst bicyclic pyrazolidinone true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2021-08-30 14:45:00 2021-08-30 14:45:04 2022-09-08 04:07:22 0000-00-00 00:00:00 2021 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 18001 75983107 Jarc_rydzi_Matej_-_Sinteza_imobilizirane_4-aminobenzojske_kisline_in_njena_uporaba_v_pripravi_im.pdf Jarc_rydzi_Matej_-_Sinteza_imobilizirane_4-aminobenzojske_kisline_in_njena_uporaba_v_pripravi_im.pdf 1 8A446CF8121A2FC770D19015490EE728 364836f9634caa48ac70a3a099970c652e32f40e2d496b1fbeab7ba8dfb02943 e300228e-098f-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=146184 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0