Sinteza in derivatizacija novih 3-benzoilamino-2H-piran-2-onov do biciklo[2.2.2]oktenskih spojin

Reberc, Katarina Barbara (author), Kranjc, Krištof (mentor)

V magistrskem delu so predstavljeni 2H-piran-2-oni, različne sintezne poti in njihova reaktivnost v različnih reakcijah. Ena izmed možnih pretvorb je preko cikloadicijskih reakcij, ki vodijo do zanimivih biciklo[2.2.2]oktenskih sistemov. V eksperimentalnem delu sem se posvetila reakcijam 2H-piran-2-onov z maleinanhidridom, pri katerih so glavni produkti različno substituirani biciklo[2.2.2]okteni, v nekaterih primerih pa je možen tudi nastanek aromatskih derivatov izobenzofurana. Analiza rezultatov omogoča vpogled v vplive na reaktivnost 2H-piran-2-onov v Diels–Alderjevih reakcijah.

• Language: Slovenian
• Keywords: 2H-piran-2-oni, biciklo[2.2.2]okteni, heterociklična kemija, Diels–Alderjeva reakcija
• Work type: Master's thesis/paper
• Typology: 2.09 - Master's Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-151024
• COBISS.SI-ID: 173236227
• Publication date in RUL: 27.09.2023

Secondary language

• Language: English
• Title: Synthesis and derivatization of novel 3-benzoylamino-2H-pyran-2-ones to bicyclo[2.2.2]octene compounds

Abstract

The master's thesis presents 2H-pyran-2-ones, different synthetic routes and their reactivity in various reactions. One of the possible transformations is via cycloaddition reactions leading to interesting bicyclo[2.2.2]octene systems. In the experimental work, I focused on the reactions of 2H-pyran-2-ones with maleic anhydride, in which the main products are variously substituted bicyclo[2.2.2]octenes, with possible formation of aromatic derivatives of isobenzofuran in some cases. Analysis of the results provides insight into the effects on the reactivity of 2H-pyran-2-ones in Diels–Alder reactions.

• Keywords: 2H-pyran-2-ones, bicyclo[2.2.2]octenes, heterocyclic chemistry, Diels–Alder reaction