Priprava 5,6-disubstituiranih 2H-piran-2-onov z aminsko ročico kot možnih dienov za sinteze biciklo[2.2.2]oktenov ter polifunkcionaliziranih anilinov

diplomsko delo

Špela Založnik (Author), Krištof Kranjc (Mentor)

Abstract

V prvem delu mojega diplomskega dela predstavim lastnosti 2H-piran-2-onov in njihovih derivatov ter periciklične reakcije, pri katerih je poseben poudarek na Diels–Alderjevi reakciji. V okviru eksperimentalnega dela sem izvedla sintezo 5-acetil-3-benzoilamino-6-metil-2H-piran-2-ona po "one-pot" metodi. Dobljeni produkt sem v naslednji stopnji ob segrevanju pod kislimi pogoji pretvorila v 3-aminski derivat ter ponovno zaščitila v 3-(4-klorobenzoilaminski) analog, nastali produkt pa je bil začetna spojina za nadaljnjo pripravo cikloaduktov: z dvakratnim prebitkom maleinanhidrida sem ga s segrevanjem v tetralinu pod refluksom pretvorila v biciklo[2.2.2]oktenski adukt, ki je nastal z Diels–Alderjevo reakcijo. Na enak način sem biciklo[2.2.2]oktenski adukt želela sintetizirati tudi iz 6-tienilnega derivata 2H-piran-2-ona. Nadalje pa sem ta adukt želela s fenilhidrazinom pretvoriti še v hidrazinski derivat.

Keywords

2H-piran-2-oni;periciklične reakcije;Diels-Alderjeva reakcija;biciklo[2.2.2]okteni;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2022
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[Š. Založnik]
UDC:	547.81(043.2)
COBISS:	126293763
Views:	43
Downloads:	19
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Preparation of 5,6-disubstituted 2H-pyran-2-ones with amine functionality as possible dienes for the synthesis of bicyclo[2.2.2]octenes and polyfunctionalized anilines
Secondary abstract:	The first part of my diploma is dedicated to characteristics of 2H-pyran-2-ones and pericyclic reactions, among which there is an emphasis on Diels–Alder reaction. In experimental part of my work I carried out a synthesis of 5-acetyl-3-benzoylamino-6-metyl-2H-pyran-2-one with one-pot method. In the next step I converted the obtained product to 3-amino derivate with heating under acidic conditions and protected this moiety again into 3-(4-chlorobenzoylamino) analog, the resulting product being starting compound for further preparation of cycloadducts: with double excess of maleic anhydride and heating in tetralin under the reflux I converted it into a bicyclo[2.2.2]octene adduct, taking place via Diels–Alder reaction. In the same manner I intended to synthesize bicyclo[2.2.2]octene adduct out of a 6-thienyl derivate of 2H-pyran-2-one. I than wanted to convert the adduct to a hydrazine derivate with phenylhydrazine.
Secondary keywords:	2H-pyrane-2-ones;organic synthesis;pericyclic reactions;Diels-Alder reaction;bicyclo[2.2.2]octenes;Pirani;Organska sinteza (kemija);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:	34 str.
ID:	16391427