Sinteza 2H-piran-2-onov 6-substituiranih z dušikovimi heterocikli kot možnih reagentov za sintezo biciklo[2.2.2]oktenov

Frešer, Maša (author), Kranjc, Krištof (mentor)

V diplomskem delu sem raziskovala sinteze substituiranih 2H-piran-2-onov, ki predstavljajo pomembne prekurzorje za nadaljnje cikloadicijske reakcije z različnimi dienofili. Za sinteze 2H-piran-2-onov sem uporabila najbolj enostavno in praktično »one pot« metodo. Pripravila sem 3-substituirane 2H-piran-2-one, dva sem nato reagirala z maleinanhidridom, pri čemer je v enem primeru uspešno nastal biciklo[2.2.2]oktenski adukt. Vse končne produkte sem analizirala in s tem potrdila njihovo molekulsko strukturo. Produkte sem analizirala s pomočjo NMR in IR spektroskopije, masne spektrometrije (HRMS) in meritvami tališč.

• Language: Slovenian
• Keywords: 2H-piran-2-on, Diels–Alderjeva reakcija, cikloadicijska 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: 2025
• PID: 20.500.12556/RUL-170315
• COBISS.SI-ID: 243661827
• Publication date in RUL: 03.07.2025

Secondary language

• Language: English
• Title: Synthesis of 2H-pyran-2-ones 6-substituted with nitrogen heterocycles as possible reagents for the synthesis of bicyclo[2.2.2.2]octenes

Abstract

In my Diploma I investigated the syntheses of substituted 2H-pyran-2-ones, which represent important precursors for further cycloaddition reactions with various dienophiles. For the syntheses of 2H-pyran-2-ones I used the simplest and most practical one-pot method. I prepared three substituted 2H-pyran-2-ones. Two prepared 2H-pyran-2-ones were then reacted with maleic anhydride to successfully yield a bicyclo[2.2.2.2]octene adduct in one case. All the final products were analysed to confirm their molecular structure. The analyses were carried out by NMR spectroscopy, IR spectroscopy, mass spectrometry (MS) and melting point measurements.

• Keywords: 2H-pyran-2-one, Diels–Alder reaction, cycloaddition reaction, bicyclo[2.2.2]octenes