20.500.12556/RUL-149151 Sinteze 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov, pretvorbe v 3-acilamino derivate ter nadaljnje cikloadicije do biciklo[2.2.2]oktenov Syntheses of 5,6-disubstituted 3-benzoylamino-2H-pyran2-ones, conversions to 3-acylamino derivatives and further cycloadditions to bicyclo[2.2.2]octenes V okviru diplomskega dela sem izvedel sinteze štirih 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov po znani "one-pot" oz. enolončni dvostopenjski metodi. Iz njih sem s segrevanjem pod kislimi pogoji poskušal odstraniti benzoilno zaščitno skupino na 3-aminski skupini. Derivate s prosto 3-aminsko skupino sem ponovno zaščitil s kislinskima kloridoma (sukcinil klorid in klorobenzoil kloridom). Pri zaščiti s sukcinil kloridom sem uspel sintetizirati in izolirati dvojni 2H-piran-2-on (kjer sta dva obroča povezana z amidnim mostičkom). Na izoliranih 2H-piran-2-onih sem nato izvedel Diels–Alderjeve cikloadicije z maleinanhidridom, pri čemer sem sintetiziral dvojne biciklo[2.2.2]oktenske adukte. Te sem v nadaljevanju modificiral s piridin-2-karbohidrazidom, piridin-3-karbohidrazidom in hidrazin hidratom. Produkt s hidrazin hidratom sem še dodatno modificiral z [1,1'-difenil]-4-karbonil kloridom. In my diploma work, I carried out syntheses of four 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones using the well-known "one-pot" two-step method. On the isolated products I attempted to remove the benzoyl protection group from the 3-amino group by heating under acidic conditions. These derivates having free 3-amino group were further reacted with two acid chlorides (succinyl chloride and chlorobenzoyl chloride). In the case of succinyl chloride, I succeeded in synthesizing and isolating a double 2H-pyran-2-one (having two rings connected with an amide bridge). I then performed Diels–Alder cycloadditions with maleic anhydride on the isolated 2H-pyran-2-ones, synthesizing bicyclo[2.2.2]octene adducts. Further on, I modified these with pyridine-2-carbohydrazide, pyridine-3-carbohydrazide and hydrazine hydrate. The hydrazine hydrate product was additionally modified with [1,1'-diphenyl]-4-carbonyl chloride. 2H-piran-2-oni Diels–Alderjeva cikloadicija biciklo[2.2.2]okteni 2H-pyran-2-ones Diels–Alder cycloaddition bicyclo[2.2.2]octenes true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2023-09-04 14:10:02 2023-09-04 14:10:04 2023-10-06 10:57:51 0000-00-00 00:00:00 2023 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 22725 167129859 Zobec_Luka_-_Sinteze_5,6-disubstituiranih_3-benzoilamino-2H-piran-2-onov,_pretvorbe_v_3-acilamin.pdf Zobec_Luka_-_Sinteze_5,6-disubstituiranih_3-benzoilamino-2H-piran-2-onov,_pretvorbe_v_3-acilamin.pdf 1 1478CD66B198EF03B58CDF688A49A3E2 b4bbdcf335825ecdc8fde681e2a05c65a3c0b4c81e08801c67e256072e28930f f804da08-4b1b-11ee-af86-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=173544 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0