Sinteza substituiranih biciklo[2.2.2]oktenov s cikloadicijami med 3-benzoilamino-2H-piran-2-onskimi derivati in maleinanhidridom ter nadaljnje pretvorbe s heterocikličnimi azinskimi sistemi

Pelko, Teja (author), Kranjc, Krištof (mentor)

V okviru magistrskega dela sem sintetizirala različne že znane 3-benzoilamino-2H-piran-2-one, ki sem jih v nadaljevanju reagirala z maleinanhidridom, pri čemer je potekla dvojna Diels–Alderjeva cikloadicijska reakcija, kot produkte pa sem dobila različno substituirane biciklo[2.2.2]oktenske sisteme. Preverila sem, če in na kakšen način izbira topila in sprememba reakcijske temperature vplivata na potek in izkoristek sinteze biciklo[2.2.2]oktenov. V naslednji stopnji sem različno substituirane biciklo[2.2.2]oktenske sisteme derivatizirala z različnimi heterocikličnimi aminskimi sistemi, pri čemer so z nukleofilno substitucijo z NH$_2$ skupno iz sukcinanhidridnih fragmentov nastali substituirani sukcinimidni fragmenti. Končni produkti so vsebovali po dva azinska obroča, vezana na sukcinimidni fragmenti. Vse spojine sem analizirala s TLC, IR, MS in $^1$H NMR spektroskopijo. Analiza produktov je pokazala, da ni vsako topilo primerno za sintezo biciklo[2.2.2]oktenskih sistemov. Uspešno sem pripravila nekaj dušikovih derivatov biciklo[2.2.2]oktenskih sistemov, ki do sedaj še niso bili sintetizirani.

• Language: Slovenian
• Keywords: 2H-piran-2-oni, Diels–Alderjeva cikloadicija, biciklo[2.2.2]okteni, različna topila, heterociklični azinski sistemi
• Work type: Master's thesis/paper
• Typology: 2.09 - Master's Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2024
• PID: 20.500.12556/RUL-160701
• COBISS.SI-ID: 206661123
• Publication date in RUL: 03.09.2024

Secondary language

• Language: English
• Title: Synthesis of substituted bicyclo[2.2.2]octenes with cycloadditions between 3-benzoylamino-2H-pyran-2-one derivatives and maleic anhydride and further transformations with heterocyclic azine systems

Abstract

As part of my master's thesis, I synthesized various already known 3-benzoylamino-2H-pyran-2-ones, which I subsequently reacted with maleic anhydride, yielding a double Diels–Alder cycloadducts. The products obtained were variously substituted bicyclo[2.2.2]octene systems. I investigated if and how the choice of solvent and the change in reaction temperature affects the course and efficiency of the bicyclo[2.2.2]octene synthesis. In the next stage, I derivatized various substituted bicyclo[2.2.2]octene systems with different heterocyclic amine systems. Through nucleophilic substitution with an NH$_2$ group on the succinic anhydride fragments, substituted succinimide fragments were formed. The final products contained two azine rings attached to the succinimide fragments. All compounds were analyzed using TLC, IR, MS, and $^1$H NMR spectroscopy. Product analysis showed that not every solvent is suitable for the synthesis of bicyclo[2.2.2]octene systems. I successfully prepared some nitrogen derivatives of bicyclo[2.2.2]octene systems that have not been synthesized before.

• Keywords: 2H-pyran-2-ones, Diels–Alder cycloaddition, bicyclo[2.2.2]octenes, different solvents, heterocyclic azine systems