Sinteza 2H-piran-2-ona iz aktiviranega ketona z zaščiteno aminsko skupino kot intermediata na poti do dvojnih sukcinanhidridnih biciklo[2.2.2]oktenov in njihovih hidrazonov

Kolar Bačnik, Bor (author), Kranjc, Krištof (mentor)

V diplomskem delu sem raziskoval možne načine zaščite proste aminske skupine (pretvorba v amid in protonacija) v aktiviranem aminofenil ketonu, ki bi omogočale njegovo pretvorbo v ustrezni 2H-piran-2-on z uporabo »one pot« sintezne poti. Po uspešni sintezi enega takšnih 2H-piran-2-onov sem se posvetil njegovi pretvorbi v dvojni biciklo[2.2.2]oktenski adukt z Diels–Alderjevo cikloadicijo dveh molekul maleinanhidrida in nadaljnji derivatizaciji s hidrazinom. Po reakciji s hidrazinom namreč nastanejo N-substituirani sukcinimidi, ki vsebujejo proste N-aminske skupine. Nukleofilnost teh aminskih skupin omogoča reakcijo z različno substituiranimi karbonilnimi spojinami; na ta način sem z različnimi meta-substituiranimi benzaldehidi sintetiziral serijo hidrazonov.

• Language: Slovenian
• Keywords: Zaščita aminske skupine, 2H-piran-2-on, Diels–Alderjeva reakcija, biciklo[2.2.2]okteni, hidrazoni.
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-148947
• COBISS.SI-ID: 165250563
• Publication date in RUL: 01.09.2023

Secondary language

• Language: English
• Title: Synthesis of 2H-pyran-2-one from an activated ketone with a protected amine group as an intermediate towards double succinic anhydride bicyclo[2.2.2]octenes and their hydrazones

Abstract

In this diploma I investigated possible methods of free amine group protection (through transformation into an amide and protonation) in an activated aminophenyl ketone which would allow its transformation into a suitable 2H-pyran-2-one. After a successful synthesis of one such 2H-pyran-2-one I focused into the formation of corresponding bicyclo[2.2.2]octenes with the Diels–Alder cycloaddition of two maleic anhydride molecules and their further derivatization with hydrazine. Such reactions produce N-substituted succinimides with free N-amine groups. Because of the nucleophilic character of these amine groups reactions with various carbonyl compounds are possible; thus I prepared a series of hydrazones with a set of meta-substituted benzaldehydes.

• Keywords: Protection of amine group, 2H-pyran-2-one, Diels–Alder reaction, bicyclo[2.2.2]octenes, hydrazones.