Maleinanhidrid kot dienofil za periciklične reakcije s substituiranimi 2H-piran-2-oni - sinteze benzofuranskih in izoindolnih sistemov

Štemberger, Lara (author), Kranjc, Krištof (mentor)

V diplomskem delu sem z enolončno metodo uspešno sintetizirala tri 2H-piran-2-one. V nadaljevanju naloge sem na enega izmed 2H-piran-2-onov s prosto 3-aminsko skupino derivatizirala z dvema različnima acil kloridoma in tako uvedla novo zaščitno skupino. Na treh 2H-piran-2-onih sem izvedla Diels–Alderjevo cikloadicijo z maleinanhidridom do biciklo[2.2.2]oktenskih aduktov, pri čemer je bil eden izmed poskusov neuspešen.

• Language: Slovenian
• Keywords: 2H-piran-2-oni, enolončna sinteza, Diels-Alderjeva cikloadicija, biciklo[2.2.2]okteni.
• 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-160147
• COBISS.SI-ID: 205750275
• Publication date in RUL: 22.08.2024

Secondary language

• Language: English
• Title: Maleic anhydride as a dienophile for pericyclic reactions with substituted 2H-pyran-2-ones - syntheses of benzofuran and isoindole systems

Abstract

In this thesis I successfully synthesised three 2H-pyran-2-ones with “one-pot” synthesis. Secondly I derivatized a 2H-pyran-2-one having a free 3-amino group with two different acyl chlorides and thus introduced a new protection group. On three 2H-pyran-2-ones, I performed the Diels–Alder cycloaddition with maleic anhydride to prepare bicyclo[2.2.2]octene adducts, however one of the attempts was unsuccessful.

• Keywords: 2H-pyran-2-ones, one-pot synthesis, Diels–Alder cycloaddition, bicyclo[2.2.2]octenes.