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Regioselektivnost in stereoselektivnost cikloadicij na primerih substituiranih 3-acilamino-2H-piran-2-onov
Kebelj, Simon (Author), Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Abstract
V okviru diplomskega dela so predstavljene sinteze nekaterih 2H-piran-2-onov, primer zamenjave zaščitne skupine na izbranem 2H-piran-2-onu ter sinteza biciklo[2.2.2]oktenskega adukta, ki sem ga pripravil iz maleinanhidrida in 3-benzoilamino-6-(2-tienil)-2H-piran-2-ona. Slednja sinteza je bila izvedena na dva različna načina – pod refluksom ter z uporabo mikrovalov. Namen je bil ugotoviti, ali bosta obe poti vodili do željenega končnega produkta, ter katera pot bo vodila do produkta z boljšim izkoristkom. V sklopu diplomskega dela je vključen tudi pregled literaturnih podatkov o regio- in stereoselektivnosti [4+2] cikloadicij, v katerih so kot dieni pogosto zastopani 2H-piran-2-oni. Te zaradi edinstvenih značilnosti 2H-piran-2-onov predstavljajo izredno močno sintezno orodje za tvorbo kompleksnejših molekul in strukturno izredno raznolikih sinteznih gradnikov.

Language:Slovenian
Keywords:Diels–Alderjeva reakcija, [4+2] cikloadicija, 2H-piran-2-on, biciklo[2.2.2]okten
Work type:Bachelor thesis/paper (mb11)
Tipology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2021
COBISS.SI-ID:70858243 This link opens in a new window
Views:128
Downloads:40
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Secondary language

Language:English
Title:Regioselectivity and stereoselectivity of cycloadditions with substituted 3-acylamino-2H-pyran-2-ones as special cases
Abstract:
In the context of this Diploma work, syntheses of some 2H-pyran-2-ones are presented. Additionally, an example of the replacement of a protecting group on a selected 2H-pyran-2-one and the synthesis of a byciclo[2.2.2]octene adduct prepared from maleic anhydride and 3-benzoylamino-6-(2-thienyl)-2H-pyran-2-one are included. The latter was performed in two different ways - under reflux conditions and by using irradiation with microwaves. The purpose was to determine whether both paths would lead to the desired end product and to find out which path would result in a better yield. This Diploma work also presents the literature data on regio- and stereoselectivity of [4+2] cycloadditions, in which 2H-pyran-2-ones are often represented as diene compounds. Due to the unique characteristics of 2H-pyran-2-ones, these reactions represent an extremely powerful synthetic tool for the formation of more complex molecules and structurally extremely diverse synthetic building blocks.

Keywords:Diels–Alder reaction, [4+2] cycloaddition, 2H-pyran-2-one, bicyclo[2.2.2]octene

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