Sinteze 6-substituiranih 3-benzoilamino-2H-piran-2-onov prek N,N-dimetilaminometilenskih intermediatov

Gomiršek, Katarina (author), Kranjc, Krištof (mentor)

V diplomskem delu sem se ukvarjala z 2H-piran-2-oni. Povzela sem njihove ključne značilnosti in opisala nekaj reakcij, zaradi katerih veljajo za sintezno precej zanimive spojine. Navedla sem tudi različne poti, po katerih je možna sinteza 2H-piran-2-onskega obroča. V zadnjem delu uvoda sem se osredotočila še na razne biološko aktivne 2H-piran-2-one. V okviru eksperimentalnega dela sem izvedla sintezo treh različnih 3-benzoilamino-2H-piran-2-onov. Izvajala sem dvostopenjsko 'one pot' reakcijo, kjer sem v prvi stopnji med seboj reagirala ustrezni keton in N, N-dimetilformamid dimetilacetal, nato pa sem produktu te reakcije dodala hipurno kislino, s pomočjo katere sem v strukturo končnega produkta uvedla 3-benzoilaminsko skupino. Produkte sem po potrebi prekristalizirala in jih nato karakterizirala tako, da sem jim izmerila tališča ter posnela NMR, IR in masne spektre. Tako pripravljeni produkti se bodo lahko uporabljali v nadaljnjih pericikličnih reakcijah.

• Language: Slovenian
• Keywords: 2H-piran-2-on, sinteza, periciklična reakcija, biološko aktivna molekula
• 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-170612
• COBISS.SI-ID: 244443395
• Publication date in RUL: 10.07.2025

Secondary language

• Language: English
• Title: Synthesis of 6-substituted 3-aminobenzoyl-2H-pyran-2-ones via N,N-dimethylaminomethylene intermediates

Abstract

The main theme of this diploma are 2H-pyran-2-ones. At the beginning I summarised their key features and reactions that make these compounds quite interesting in the field of organic synthesis. I have also listed and described some different possibilities to synthesise the 2H-pyran-2-one ring. Lastly, I focused on some examples of biologically active 2H-pyran-2-ones. As the part of practical work, syntheses of three different 3-benzoylamino-2H-pyran-2-ones by two step ‘one-pot’ reaction were carried out. I started by reacting a ketone and N,N-dimethylformamide dimethylacetal with each other and then to carry out the second step of the synthesis I added hippuric acid to the product of the first reaction to introduce the 3-benzoylamino group into the structure of the final product. If needed, the products were recrystallized and then they were analysed by measuring their melting points and recording their NMR, IR and mass spectra. These products will be further used in different pericyclic reactions.

• Keywords: 2H-pyran-2-one, synthesis, pericyclic reaction, biologically active molecule