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

Založnik, Špela (author), Kranjc, Krištof (mentor)

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.

• Language: Slovenian
• Keywords: 2H-piran-2-oni, organska sinteza, periciklične reakcije, Diels–Alderjeva reakcija, biciklo[2.2.2]okteni
• 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-139717
• COBISS.SI-ID: 126293763
• Publication date in RUL: 06.09.2022

Secondary language

• Language: English
• 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

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.

• Keywords: 2H-pyrane-2-ones, organic synthesis, pericyclic reactions, Diels–Alder reaction, bicyclo[2.2.2]octenes