Sinteze substituiranih 2H-piran-2-onskih prekurzorjev za nadaljnje cikloadicijske reakcije z maleinanhidridom kot dienofilom

Kostanjšek, Žan (author), Kranjc, Krištof (mentor)

V diplomskem delu sem raziskoval sinteze substituiranih 2H-piran-2-onov, ki predstavljajo pomembne prekurzorje za nadaljnje cikloadicijske reakcije z različnimi dienofili. Za sinteze 2H-piran-2-onov sem uporabljal najbolj enostavno in praktično »one pot« metodo. Na enem izmed 2H-piran-2-onov sem izpeljal tudi reakcijo odstranitve benzoilne zaščitne skupine; produkt opisane reakcije se lahko uporablja v nadaljnjih sintezah za uvedbo nove zaščitne skupine. Pripravljen 2H-piran-2-on sem reagiral z maleinanhidridom, pri čemer sem izoliral nastal biciklo[2.2.2]oktenski adukt. Vse končne produkte sem tudi analiziral in s tem potrdil njihovo molekulsko strukturo. Za analize sem uporabil NMR spektroskopijo, IR spektroskopijo, (MS) masno spektrometrijo in meritve tališč.

• Language: Slovenian
• Keywords: 2H-piran-2-on, Diels–Alderjeva reakcija, maleinanhidrid, cikloadicijska reakcija
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2024
• PID: 20.500.12556/RUL-161070
• COBISS.SI-ID: 213386755
• Publication date in RUL: 06.09.2024

Secondary language

• Language: English
• Title: Synthesis of substituted 2H-pyran-2-one precursors for further cycloaddition reactions with maleic anhydride as dienophile

Abstract

In my diploma thesis 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 most straightforward and practical "one-pot" method. On one of the 2H-pyran-2-ones I have also carried out a removal of the benzoyl protecting group; the product thus obtained can be used in further syntheses to introduce a new protecting group. The prepared 2H-pyran-2-one was reacted with maleic anhydride to isolate the resulting bicyclo[2.2.2]octene adduct. All the final products were also analysed to confirm their molecular structure. NMR spectroscopy, IR spectroscopy, (MS) mass spectrometry and melting point measurements were used for the analyses.

• Keywords: 2H-pyran-2-one, Diels–Alder reaction, maleic anhydride, cycloaddition reaction