Sinteza različnih 3-acilamino substituiranih 6-metil-2H-piran-2-onov

Vavpetič, Ida (author), Kranjc, Krištof (mentor)

V diplomskem delu sem se ukvarjala z 2H-piran-2-oni. Najprej sem navedla njihove ključne lastnosti in izpostavila njihove značilnosti ter njihovo vsestransko uporabnost v kemiji. Nato sem opisala različne sintezne poti za nastanek 2H-piran-2-onskega obroča. V zadnjem delu uvoda sem še nekaj napisala o pericikličnih reakcijah, bolj izpostavila Diels–Alderjeve reakcije in kako 2H-piran-2-oni reagirajo pri takšnih reakcijah. V okviru eksperimentalnega dela sem izvedla sintezo štirih različno substituiranih 6-metil-2H-piran-2-onov. Dva sem sintetizirala po »one-pot« metodi, kjer v prvi stopnji reagirata ustrezni keton in DMFDMA (C$_1$-sinton), nato pa sem v drugi stopnji dodala hipurno kislino, s katero sem v končni produkt uvedla 3-benzoilaminsko skupino. Korake sinteze tretjega produkta sem izvedla v drugem vrstnem redu, tako da je v prvi stopnji hipurna kislina reagirala s TEOF (C$_1$-sinton) do oksazolona in potem šele dodala ustrezni keton. Četrti produkt pa sem sintetizirala z odščito in ponovno zaščito 3-aminske skupine 2H-piran-2-onskega derivata. Produkte sem po potrebi prekristalizirala in jim za karakterizacijo izmerila tališča ter posnela $^1$H NMR spektre. Tako pripravljeni produkti se lahko uporabljajo v nadaljnjih pericikličnih reakcijah.

• Language: Slovenian
• Keywords: 2H-piran-2-on, sinteza, »one-pot« metoda, Diels–Alderjeva reakcija
• 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-171585
• COBISS.SI-ID: 248539139
• Publication date in RUL: 28.08.2025

Secondary language

• Language: English
• Title: Synthesis of various 3-acylamino substituted 6-methyl-2H-pyran-2-ones

Abstract

2H-Pyran-2-ones are the main theme of this diploma. At the beginning, I listed their key properties and highlighted characteristics of their versatile use in chemistry. I also described various synthetic routes for the formation of the 2H-pyran-2-one ring. The last part of the introduction is focused on pericyclic reactions, highlighting Diels–Alder reactions and how 2H-pyran-2-ones react in such reactions. As part of the experimental work, I carried out the synthesis of four differently substituted 6-methyl-2H-pyran-2-ones. I synthesized two of them using a "one-pot" approach, where in the first stage the corresponding ketone and DMFDMA (C$_1$-synthone) react, and then in the second stage hippuric acid is added to introduce the 3-benzoylamino group into the structure of the final product. I carried out the synthetic steps for the preparation of the third product in a different order than for the first two: in the first stage hippuric acid reacted with TEOF (different C$_1$-synthone) to oxazolone and only then the corresponding ketone was added. The fourth product was synthesized by deprotection and reprotection of the 3-amine group of 2H-pyran-2-one derivate. The products were recrystallized if necessary and their melting points and $^1$H NMR spectra were recorded for characterization. These products can be used in further pericyclic reactions.

• Keywords: 2H-pyran-2-one, synthesis, “one-pot” method, Diels–Alder reaction