Sinteze 6-substituiranih 3-benzoilamino 2H-piran-2-onov in nadaljnja cikloadicija z maleinanhidridom

Mulec, Karolina (author), Kranjc, Krištof (mentor)

V diplomskem delu je moja glavna tematika sinteza štirih različnih 2H-piran-2-onov po »one pot« metodi, ki je od vseh najbolj enostavna in praktična. Poleg sinteze 2H-piran-2-onov sem 2H-piran-2-on z že odstranjeno benzoilno zaščito, torej s prosto 3-aminsko skupino, derivatizirala z dvema različnima acil kloridoma in tako uvedla dve novi zaščitni skupini. Tako sem sintetizirala 2H-piran-2-ona s 4-metoksibenzoilno in z 2-nitrobenzoilno zaščitno skupino. Enega od pripravljenih 2H-piran-2-onov z benzoilno zaščitno skupino sem reagirala z maleinhidridom in sintetizirala biciklo[2.2.2]oktenski adukt. Vseh sedem končnih produktov sem analizirala z IR spektroskopijo, nekatere nove produkte pa tudi z NMR spektroskopijo, masno spektrometrijo (MS) in meritvijo tališč.

• Language: Slovenian
• Keywords: 2H-piran-2-on, Diels–Alderjeva reakcija, maleinanhidrid, 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-171839
• COBISS.SI-ID: 252438275
• Publication date in RUL: 03.09.2025

Secondary language

• Language: English
• Title: Syntheses of 6-substituted 3-benzoylamino 2H-pyran-2-ones and further cycloaddition with maleic anhydride

Abstract

The main topic of my thesis is the synthesis of four different 2H-pyran-2-ones using the "one pot" synthesis, which is the simplest and most practical of all. In addition to the synthesis of 2H-pyran-2-ones, I derivatized 2H-pyran-2-one with the benzoyl protection already removed, i.e., with a free 3-amino group, with two different acyl chlorides, thus introducing two new protective groups. In this way, I synthesized 2H-pyran-2-one with a 4-methoxybenzoyl and a 2-nitrobenzoyl protecting group. I reacted one of the prepared 2H-pyran-2-ones having a benzoyl protecting group, with maleic anhydride and synthesized a bicyclo[2.2.2]octene adduct. All seven final products were analyzed by IR spectroscopy, and some of the new products were also analyzed by NMR spectroscopy, mass spectrometry (MS), and melting point measurement.

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