Sinteze novih 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov ter nadaljnje cikloadicije do izobenzofuranskih ali biciklo[2.2.2]oktenskih derivatov

magistrsko delo

Klemen Kozlovič (Author), Krištof Kranjc (Mentor), Iztok Turel (Thesis defence commission member), Franc Perdih (Thesis defence commission member)

Abstract

V magistrskem delu sem raziskoval Diels–Alderjevo reakcijo med substituiranimi 2H-piran-2-oni in maleinanhidridom. Izhodne 2H-piran-2-one sem pripravil z enoločno sintezo, pri čemer so nastali različno substituirani 3-benzoilamino-2H-piran-2-oni. Slednji pri reakcijah z maleinanhidridom pod termičnimi pogoji običajno tvorijo enega izmed dveh možnih produktov: biciklični dvojni adukt (derivatiziran biciklo[2.2.2]okten) ali termodinamsko stabilnejši aromatski produkt (derivat izobenzofurana). Z optimizacijo reakcijskih pogojev sem poskušal pripraviti ter izolirati obe vrsti produktov. Izkazalo se je, da je reaktivnost 2H-piran-2-onov, ki vsebujejo elektron donorske substituente, pri reakciji z maleinanhidridom večja kot je reaktivnost 2H-piran-2-onov z elektron privlačnimi substituenti; v obeh primerih nastanejo biciklični dvojni adukti z dobrimi izkoristki, v drugem primeru pa tudi aromatizirani izobenzofuranski produkti. 2H-piran-2-oni z elektron donorskimi substituenti torej preferenčno tvorijo biciklične adukte, ki se v večini primerov tudi po daljšem reakcijskem času in višji reakcijski temperaturi slabo pretvarjajo v aromatske.

Keywords

piranoni;2H-piran-2-oni;cikloadicije;Diels-Alderjeva reakcija;aromatizacija;biciklo[2.2.2]okten;magistrska dela;

Data

Language:	Slovenian
Year of publishing:	2022
Typology:	2.09 - Master's Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[K. Kozlovič]
UDC:	547.81(043.2)
COBISS:	116902915
Views:	85
Downloads:	36
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Synthesis of novel 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones and further cycloadditions towards isobenzofuran or bicyclo[2.2.2]octene derivatives
Secondary abstract:	In the present work I investigated the Diels–Alder reaction between substituted 2H-pyran-2-ones and maleic anhydride. The starting 2H-pyran-2-ones were synthesised by “one pot” synthesis, resulting in various substituted 3-benzoylamino-2H-pyran-2-ones. The latter when reacted with maleic anhydride under thermal conditions usually form one of the two possible products: a bicyclic double adduct (derivatized bicyclo[2.2.2] octene) or a thermodynamically more stable aromatic product (isobenzofuran derivative). By optimizing the reaction conditions, I tried to prepare and isolate both types of products. The reactivity of 2H-pyran-2-ones with electron donor substituents in the reaction with maleic anhydride has been shown to be greater than the reactivity of 2H-pyran-2-ones with electron-withdrawing substituents, resulting in the formation of bicyclic double adducts (with good yields) in the former case and aromatic isobenzofuran products in the latter. In contrast, 2H-pyran-2-ones with electron donor substituents preferentially form a bicyclic adduct, which in most cases is poorly converted to aromatic even after a long reaction time and higher reaction temperature.
Secondary keywords:	2H-pyran-2-ones;Diels-Alder cycloaddition;aromatization;bicyclo[2.2.2]octene;Pirani;Univerzitetna in visokošolska dela;
Type (COBISS):	Master's thesis/paper
Study programme:	1000375
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages:	64 str.
ID:	15841042