diplomsko delo
Bor Kolar Bačnik (Author), Krištof Kranjc (Mentor)

Abstract

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.

Keywords

zaščita aminske skupine;2H-piran-2-on;Diels-Alderjeva reakcija;biciklo[2.2.2]okteni;hidrazoni;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [B. Kolar Bačnik]
UDC: 547.81(043.2)
COBISS: 165250563 Link will open in a new window
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Other data

Secondary language: English
Secondary 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
Secondary 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.
Secondary keywords: protection of amine group;2H-pyran-2-one;Diels-Alder reaction;bicyclo[2.2.2]octenes;hydrazones;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: 39 str.
ID: 19876359