20.500.12556/RUL-141346 Uporaba različnih monokarbonilnih spojin z aktivirano metilno skupino za sintezo novih 3-benzoilamino-2H-piran-2-onov Use of various monocarbonyl compounds with an activated methyl group for synthesis of novel 3-benzoylamino-2H-pyran-2-ones Magistrska naloga predstavlja sintezo novih 3-benzoilamino-2H-piran-2-onov iz različnih monokarbonilnih spojin z aktivirano metilno skupino. V uvodnem delu je opisana razširjenost in pomen 2H-piran-2-onov v naravi, za kaj so koristni in kako jih pripravimo. Na kratko so opisane kemijske in spektroskopske značilnosti 2H-piran-2-onov ter kako jih lahko uporabimo v nadaljnjih reakcijah. Eksperimentalni del opisuje sintezo novih 3-benzoilamino-2H-piran-2-onov po dvostopenjski »one pot« metodi. V prvi stopnji sem izhodno monokarbonilno spojino segrevala ob prisotnosti DMFDMA (v vlogi C1-sintona). Nastalo zmes sem destilirala pod znižanim tlakom in nato temu enaminonskemu intermediatu dodala hipurno kislino in acetanhidrid, ki in situ reagirata v oksazolonski derivat. Zopet je sledilo segrevanje nato pa izolacija (obarjanje) in čiščenje dobljenih 3-benzoilamino-2H-piran-2-onov. Končne spojine sem analizirala s TLC, IR, 1H NMR in MS. Medsebojna primerjava analiz produktov razkriva razlike v njihovi reaktivnosti in izkoristkih. The Master's thesis presents the synthesis of new 3-benzoylamino-2H-pyran-2-ones from various monocarbonyl compounds with an activated methyl group. The introductory part describes where 2H-pyran-2-ones are found in nature, their importance and applications as well as how they are prepared. The chemical and spectroscopic characteristics of 2H-pyran-2-ones and how they can be used in further transformations are also briefly described. The experimental part describes the synthesis of new 3-benzoylamino-2H-pyran-2-ones by the one pot method, consisting of two steps. In the first step the starting monocarbonyl compound was heated in the presence of DMFDMA (acting as a C1-synthon). Distillation of the resulting mixture under reduced pressure and the addition of hippuric acid and acetic anhydride (in situ forming oxazolone derivative) to this enaminone intermediate with additional heating, followed by isolation (precipitation) and purification gave the final products 3-benzoylamino-2H-pyran-2-ones. I analyzed the final compounds by TLC, IR, 1H NMR and MS. Comparison of products and their analyses reveals the differences in reactivity and influences on the yields. organska sinteza heterociklične spojine 2H-piran-2-oni hipurna kislina monokarbonilne spojine oksazolon organic synthesis heterocyclic compounds 2H-pyran-2-ones hippuric acid monocarbonyl compounds oxazolone true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2022-09-28 15:35:00 2022-09-28 15:35:03 2022-12-02 13:21:59 0000-00-00 00:00:00 2022 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 9941 132114179 Lipovsek_Agata_-_Uporaba_razlicnih_monokarbonilnih_spojin_z_aktivirano_metilno_skupino_za_sintez.pdf Lipovsek_Agata_-_Uporaba_razlicnih_monokarbonilnih_spojin_z_aktivirano_metilno_skupino_za_sintez.pdf 1 83A1FCA6F93421F53047D4073C8F113E 8dab6c99e776523f7ef103fdc393815ec59716803ef4bffcf2d2eb52ad79c2cd 59838af4-3f32-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=162382 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0