Priprava premostenih bicikličnih [2.2.2] sistemov z Diels-Alderjevimi reakcijami zaščitenih 3-amino-2H-piran-2-onov

diplomsko delo na univerzitetnem študiju Kemija

Grega Pavlin (Author), Krištof Kranjc (Mentor)

Abstract

V diplomskem delu so predstavljene izbrane sinteze 6-substituiranih in 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov, primer odščite in zaščite aminske skupine na 2H-piran-2-onu ter sinteza biciklo[2.2.2]oktenskih aduktov. V sklopu svojega dela sem uporabil različne sintezne metode za pripravo 2H-piran-2-onov. V okviru sinteze dvojnih cikloaduktov sem preučil različne prijeme, s katerimi bi lahko prišel do končnega produkta. Tako sem v eksperimentalnem delu želel ugotoviti, kako se uporaba mikrovalovnega obsevanja in visokega tlaka pri sintezi izkažeta v primerjavi z bolj konvencionalnimi pogoji, ki pa so običajno manj okolju prijazni (škodljiva topila, refluks). Pretvorbe sem pri reakcijah preverjal s TLC in spektroskopskimi metodami (IR, 1H NMR, HRMS). Pri mojih primerih pa so željeni dvojni cikloadukti nastali le pri konvencionalnem segrevanju (refluks). Izvedba odščite in zaščite aminske skupine ter sama sinteza 2H-piran-2-onov je bila uspešna v zadovoljivih izkoristkih.

Keywords

organska sinteza;heterociklične spojine;derivati pirana;2H-piran-2-on;Diels-Alderjeva reakcija;cikloadicija;mikrovalovi;odščita/zaščita;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2020
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[G. Pavlin]
UDC:	547.81(043.2)
COBISS:	15918851
Views:	904
Downloads:	242
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Preparation of bridged bicyclic [2.2.2] systems with Diels–Alder reactions of masked 3-amino-2H-pyran-2-ones
Secondary abstract:	In this diploma syntheses of selected 6-substituted and 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones, an example of the deprotection and protection of an amine group on 2H-pyran-2-one and the synthesis of bicyclo[2.2.2]octene aducts are presented. As part of my work, I applied different synthetic methods for 2H-pyran-2-ones preparation. As a part of the synthesis of double cycloaducts, I have explored various methods that could yield the final product. Thus, in the experimental part, I wanted to find out how the use of microwave irradiation and high pressure in synthesis turns out in comparison to the more conventional, but less green methods (harmful solvents, reflux). I followed the reaction conversions by TLC and spectroscopic methods (IR, 1H NMR, HRMS). Under the conditions applied, the desired double cycloaducts were obtained only under conventional heating (reflux). The removal and introduction of the amine protection group and the synthesis of 2H-pyran-2-ones were successful in satisfactory yields.
Secondary keywords:	2H-pyran-2-one;Diels-Alder reaction;cycloaddition;microwaves;deprotection/protection;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo
Pages:	27 str.
ID:	11705508