20.500.12556/RUL-140589 Sinteza cinolinskih derivatov iz o-vinilanilinov Sinthesis of cinnoline derivates from o-vinylanilines V magistrskem delu smo preučevali, kako raznolik nabor cinolinov lahko pripravimo z novo reakcijo, katalizirano s p-toluensulfonsko kislino. Reakcija ciklizacije iz o-vinilanilinov in terc-butil nitrita poteka pri sobni temperaturi v topilu etil acetatu in s katalitsko količino p-toluensulfonske kisline. Vse nastale spojine smo okarakterizirali s pomočjo tehnik jedrske magnetne resonance, masne spektrometrije visoke ločljivosti, visokotlačne tekočinske kromatografije in infrardeče spektroskopije. Trdnim spojinam smo izmerili še tališče. o-Vinilaniline smo pripravili iz fenilacetilena in različno substituiranih anilinov s heterogenim katalizatorjem montmorilonitom K-10. Reakcijske pogoje smo optimizirali na modelni reakciji. Izolirali in okarakterizirali smo stranski produkt, derivat kinolin, ki je nastal pri reakciji. Na modelni reakciji smo optimizirali tudi reakcijo sinteze cinolinov. Osredotočili smo se na ekstrakcijo in čiščenje produkta. In this work, we have investigated the wide range of cinnolines that we can produce using the new reaction catalyzed by p-toluenesulfonic acid. The cyclization reaction takes place at room temperature in ethyl acetate. In this process, o-vinylanilines and tert-butyl nitrite are used as starting compounds and a catalytic amount of p-toluenesulfonic acid. All synthesized compounds were characterized by nuclear magnetic resonance, mass spectrometry, high- pressure liquid chromatography and infrared spectroscopy. The melting points of the solid compounds were measured. o-Vinylanilines were synthesized from phenylacetylene and various anilines. The heterogeneous catalyst montmorillonite K-10 was used for the reaction. A model reaction was carried out to optimize the reaction conditions. The product of a side reaction was isolated and characterized as a quinoline derivative. A model reaction for cinnoline synthesis was used to optimize the reaction conditions. We mainly focused on extraction and purification. o-vinilanilin cinolin p-toluensulfonska kislina kinolin o-vinylaniline cinnoline p-toluenesulfonic acid quinoline true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2022-09-16 07:55:01 2022-09-16 07:55:03 2022-11-25 12:41:20 0000-00-00 00:00:00 2022 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 21952 131026435 Magistrsko_delo_Marko_Gabrovsek.pdf Magistrsko_delo_Marko_Gabrovsek.pdf 1 D7F0CC4BF9ADF5FE5925A3A039746B84 108bcde714ee10b031c3fda08c015a3836bf42f14ba12b4a9b83106a38c9fe84 791e984d-3e36-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=162249 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0