Sodobni okolju prijazni pristop v organski kemiji 2H-piran-2-onskih derivatov: sinteze, reaktivnost, uporabnost

Tominec, Leja (author), Kranjc, Krištof (mentor)

V diplomskem delu najprej opišem kemijske lastnosti 2H-piran-2-onov. Razčlenim vrste naravnih spojin, v katerih se pojavi izoliran ali pripojen skelet piranonov kot sestavni del spojine. Opisani so bufadienolidi, stiril-, 4-hidroksi-, 6-substituirani-2H-piran-2-oni, kumarini in kromoni. Posvetim se tudi aktualni temi zelene kemije. Njena načela usmerjajo načrtovanje kemijskih produktov in procesov tako, da se prepreči onesnaževanje ter zmanjša negativne vplive kemikalij na zdravje in okolje. Pomembna vira za raziskovanje zelenih načinov aktivacije reakcij in zelenih procesov sta obsevanje z mikrovalovi in uporaba visokega tlaka. V delu opišem sinteze 2H-piran-2-onov z reakcijami kondenzacije, z Wittigovo in Baylis‒Hillmanovo reakcijo, s povečanjem obroča, s ciklizacijo s sledečo premestitvijo, z jodolaktonizacijo in sinteze z uporabo organskih ali kovinskih katalizatorjev. V eksperimentalnem delu opišem praktično opravljeni sintezi 6-(2-furil)-3-benzoilamino- in 3-benzoilamino-6-(4-metilfenil)-2H-piran-2-ona po 'one pot' metodi, ki jo je razvil Kepe s sodelavci.

• Language: Slovenian
• Keywords: 2H-piran-2-oni, [4+2] cikloadicije, naravne spojine, zelena kemija, mikrovalovi, visok tlak
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2020
• PID: 20.500.12556/RUL-119509
• COBISS.SI-ID: 29672707
• Publication date in RUL: 09.09.2020

TOMINEC, Leja, 2020, Sodobni okolju prijazni pristop v organski kemiji 2H-piran-2-onskih derivatov: sinteze, reaktivnost, uporabnost [online]. Bachelor’s thesis. [Accessed 31 March 2025]. Retrieved from: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=eng&id=119509

Secondary language

• Language: English
• Title: Contemporary environment-friendly approach in organic chemistry of 2H-pyran-2-one derivatives: Syntheses, reactivity, application

Abstract

This diploma work describes chemical properties of 2H-pyran-2-ones. It goes over types of naturally occurring compounds, with pyranone framework as an isolated structure or fused into a polycyclic compound. It describes bufadienolide, styryl-, 4-hydroxy-, 6-substituted-2H-pyran-2-ones, coumarins and chromones. It addresses the topica of green chemistry. Its principles direct planning of chemical products and processes in such a way as to prevent pollution and decrease negative effects of chemicals on health and environment. Important sources for research of green approaches to activate the reactions are microwave irradiation and use of high pressure. The synthesis of 2H-pyran-2-ones with the application of reactions of condensation, Wittig’s and Baylis‒Hillmans reaction, ring expansion strategy and rearrangement-cyclization, iodolactonization and use of organo or metal catalysts are described. In the experimental part a description of two synthesis, namely of 6-(2-furyl)-3-benzoylamino- and 3-benzoylamino-6-(4-methylphenyl)-2H-pyran-2-one as conducted via ‘one pot’ method developed by Keppe and co-workers, is provided.

• Keywords: 2H-pyran-2-ones, [4+2] cycloadditions, natural compounds, green chemistry, microwaves, high pressure