Dvostopenjska sintezna pot do polisubstituiranih 3-acilamino-2H-piran-2-onov ter poizkusi nadaljnjih pretvorb do biciklo[2.2.2]oktenskih sistemov

Fendre, Dominik (author), Kranjc, Krištof (mentor)

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.

• Language: Slovenian
• Keywords: Diels–Alderjeva reakcija, 2H-piran-2-on, biciklo[2.2.2]oktenski adukt, maleinanhidrid, hidrazin, GABA, kislinski klorid
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-139467
• COBISS.SI-ID: 125613571
• Publication date in RUL: 02.09.2022

Secondary language

• Language: English
• Title: Two-step synthesis route to polysubstituted 3-acylamino-2H-pyran-2-ones and attempts at further conversions to bicyclo[2.2.2]octene systems

Abstract

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.

• Keywords: Diels–Alder reaction, 2H-pyran-2-one, bicyclo[2.2.2]octene adduct, maleic anhydride, hydrazine, GABA, acid chloride