diplomsko delo
Ida Vavpetič (Author), Krištof Kranjc (Mentor)

Abstract

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.

Keywords

2H-piran-2-oni;"one-pot" metoda;periciklične cikloadicije;Diels-Alderjeva reakcija;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [I. Vavpetič]
UDC: 547.81(043.2)
COBISS: 248539139 Link will open in a new window
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Downloads: 21
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Other data

Secondary language: English
Secondary title: Synthesis of various 3-acylamino substituted 6-methyl-2H-pyran-2-ones
Secondary 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.
Secondary keywords: 2H-pyran-2-one;synthesis;"one-pot" method;Diels-Alder reaction;Pirani;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Type (COBISS): Bachelor thesis/paper
Study programme: 1000373
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages: 1 spletni vir (1 datoteka PDF (24 str.))
ID: 27261874