20.500.12556/RUL-102625 SINTEZA NEKATERIH 5,6-DISUBSTITUIRANIH 3-BENZOILAMINO-2H-PIRAN-2-ONOV IN NJIHOVA UPORABA V CIKLOADICIJAH Z MALEINANHIDRIDOM IN N-SUBSTITUIRANIM MALEIMIDOM SYNTHESIS OF SOME 5,6-DISUBSTITUTED 3-BENZOYLAMINO-2H-PYRAN-2-ONES AND THEIR USE IN CYCLOADDITIONS WITH MALEIC ANHYDRIDE AND N-SUBSTITUTED MALEIMIDE V diplomskem delu so predstavljene enolončne sinteze 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov. Preučil sem različne metode, tudi uporabo mikrovalovnega obsevanja in sinteze pod visokim tlakom, primerne za izvajanje cikloadicij sintetiziranih 2H-piran-2-onov na maleinanhidrid in derivate maleimida. V eksperimentalnem delu sem želel ugotoviti, če so ti novejši pristopi primerni za sinteze izbranih biciklo[2.2.2]oktenskih aduktov, saj literaturni postopki vključujejo uporabo škodljivih topil, segrevanje pod refluksom in daljše reakcijske čase, kar vse predstavlja okolju neprijazne reakcijske pogoje. Sintetizirane produkte sem ovrednotil s TLC in spektroskopskimi metodami (1H NMR, IR, HRMS). Zaključil sem, da je enolončna metoda sinteze 2H-piran-2-onov uspešna z zadovoljivimi izkoristki, željeni cikloadukti pa nastanejo le z uporabo klasičnih pogojev segrevanja (refluks). In this diploma I present one-pot synthetic approaches to 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones. Different methods were investigated, including microwave irradiation and high-pressure conditions, that can be used to prepare cycloadducts between 2H-pyran-2-ones and maleic anhydride, and maleimide derivatives respectively. In the experimental work I wanted to evaluate new approaches to the synthesis of the desired bicyclo[2.2.2]octene adducts, since the literature procedures use hazardous solvents, heating under reflux and longer reaction times which all represent environmentally detrimental reaction conditions. The synthesized products were characterized by TLC and spectroscopic methods (1H NMR, IR, HRMS). I concluded that the one-pot method of preparing 2H-pyran-2-ones results in satisfactory yiels, however, conventional approaches have to be used to successfully synthesize the desired cycloadducts. 2H-piran-2-on enolončna sinteza cikloadicija Diels–Alderjeva reakcija mikrovalovna sinteza 2H-pyran-2-one one-pot synthesis cycloaddition Diels–Alder reaction microwave synthesis true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2018-09-05 11:05:03 2018-09-05 11:05:08 2022-08-15 03:42:58 0000-00-00 00:00:00 2018 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 4972 1537884867 Ponikvar_Ziga_-_SINTEZA_NEKATERIH_5,6-DISUBSTITUIRANIH_3-BENZOILAMINO-2H-PIRAN-2-ONOV_IN_NJIHOVA.pdf Ponikvar_Ziga_-_SINTEZA_NEKATERIH_5,6-DISUBSTITUIRANIH_3-BENZOILAMINO-2H-PIRAN-2-ONOV_IN_NJIHOVA.pdf 1 79831DA2C4845F652B807CE2649A4BD8 340aea96b68831b1f219003e8d3c792d7d7c4a56c7d96ccfa7278db295222205 938403b9-a1b5-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=112979 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0