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

diplomsko delo

Dominik Fendre (Author), Krištof Kranjc (Mentor)

Abstract

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.

Keywords

cikloadicije;Diels-Alderjeva reakcija;2H-piran-2-on;biciklo[2.2.2]oktenski adukt;maleinanhidrid;hidrazin;GABA;kislinski klorid;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2022
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[D. Fendre]
UDC:	547.81(043.2)
COBISS:	125613571
Views:	36
Downloads:	11
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary 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
Secondary 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.
Secondary keywords:	Diels-Alder reaction;2H-pyran-2-one;bicyclo[2.2.2]octene adduct;maleic anhydride;hydrazine;GABA;acid chloride;Pirani;Univerzitetna in visokošolska dela;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages:	66 str.
ID:	16354540