20.500.12556/RUL-139467 Dvostopenjska sintezna pot do polisubstituiranih 3-acilamino-2H-piran-2-onov ter poizkusi nadaljnjih pretvorb do biciklo[2.2.2]oktenskih sistemov Two-step synthesis route to polysubstituted 3-acylamino-2H-pyran-2-ones and attempts at further conversions to bicyclo[2.2.2]octene systems V diplomskem delu sem raziskoval sinteze 3-acilamino-2H-piran-2-onov ter derivatizacije zaščite na 3-aminski skupini. Tako sem na prosto 3-aminsko skupino uvedel novo zaščito, ki je vsebovala 4-nitrobenzoilno skupino, da bi jo kasneje poizkusil reducirati s hidrogeniranjem v prisotnosti heterogenega katalizatorja. Z dvojnim kislinskim kloridom sem s prosto 3-aminsko skupino v 2H-piran-2-onu pripravil dvojni 2H-piran-2-on z amidnim mostičkom, ki je z maleinanhidridom lahko tvoril dvojni biciklo[2.2.2]oktenski adukt (z amidnim mostičkom). Poizkusil sem tudi različne sinteze dvojnih 2H-piran-2-onov z alkilnim mostičkom, vendar neuspešno. Pripravljene 2H-piran-2-one sem reagiral z maleinanhidridom, pri čemer sem izoliral nastale dvojne biciklo[2.2.2]oktenske adukte. Le-te sem modificiral s hidrazinom, etanolaminom ter γ-aminobutanojsko kislino. Hidrazinskih derivatov mi z aldehidom ni uspelo pretvoriti v hidrazone, s kislinskim kloridom sem pa uspešno aciliral hidrazinsko skupino. In this diploma, I investigated synthesis of 3-acylamino-2H-pyran-2-ones and further derivatizations of their protecting group on the 3-amino moiety. Further, I introduced a new protecting group on the 3-amino motif, that contained a 4-nitrobenzoyl group, which I later attempted to reduce with hydrogenation on heterogeneous catalyst. With a double acid chloride reacting with a free 3-amino group of a 2H-pyran-2-one system, I successfully synthesised a double 2H-pyran-2-one, containing an amide linker; consequent reaction with maleic anhydride provided a double bicyclo[2.2.2]octene adduct (with a amide linker). I also tried various syntheses of double 2H-pyran-2-ones with an alkyl linker, but without success. I reacted the prepared 2H-pyran-2-ones with maleic anhydride, isolating the resulting bicyclo[2.2.2]octene double adducts. I modified them with hydrazine, ethanolamine and γ-aminobutyric acid. I was unable to convert the hydrazine derivatives into hydrzones with an aldehyde, but I successfully acylated the hydrazine group with an acid chloride. Diels–Alderjeva reakcija 2H-piran-2-on biciklo[2.2.2]oktenski adukt maleinanhidrid hidrazin GABA kislinski klorid Diels–Alder reaction 2H-pyran-2-one bicyclo[2.2.2]octene adduct maleic anhydride hydrazine GABA acid chloride true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2022-09-02 12:50:00 2022-09-02 12:50:03 2022-10-14 09:36:39 0000-00-00 00:00:00 2022 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 21761 125613571 Fendre_Dominik_-_Dvostopenjska_sintezna_pot_do_polisubstituiranih_3-acilamino-2H-piran-2-onov_te.pdf Fendre_Dominik_-_Dvostopenjska_sintezna_pot_do_polisubstituiranih_3-acilamino-2H-piran-2-onov_te.pdf 1 15988C572298B466B221A6131E138CFE 77748e4c1b413ee30aae22497485c67bf19558ba3941fc520398b4cc784bf378 f59c5e10-2aac-11ed-92af-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=160036 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0