diplomsko delo
Gašper Možina (Avtor), Krištof Kranjc (Mentor)

Povzetek

V diplomskem delu je predstavljena sinteza nekaterih 2H-piran-2-onov in njihova pretvorba v Diels–Alderjevi reakciji. 2H-piran-2-oni so aromatske organske molekule, ki v naravi sestavljajo spojine mnogih organizmov, v organski kemiji pa predstavljajo predvsem zelo uporabne sintezne intermediate. Njihova sinteza je v tem delu potekala po metodi t. i. enolončne sinteze, pri kateri vse reakcije izvajamo brez vmesne izolacije. Dobljeni produkti so čisti in le redko je bilo potrebno dodatno čiščenje. Sintetiziran 3-benzoilamino-6-(2-tienil)-2H-piran-2-on sem v vlogi diena uporabil pri Diels–Alderjevi reakciji (znani tudi kot [4+2] cikloadicije) z maleinhidridom ob segrevanju pod refluksom in dobil biciklo[2.2.2]oktenski produkt. Iz 5,6-disubstituiranega 3-benzoilamino-2H-piran-2-ona sem s hidrolizo amidne vezi odstranil zaščitno skupino. Dobljeni amin ni zelo obstojen, zato sem z reakcijo aciliranja nanj uvedel novo zaščitno skupino, pri tem pa sem uporabil ciklopropankarbonil klorid. Vse sintetizirane produkte sem okarakteriziral z ustreznimi analitskimi metodami (spektroskopija IR, TLC kromatografija).

Ključne besede

derivati pirana;2H-piran-2-oni;Diels-Alderjeva reakcija;enolončna sinteza;maleinhidrid;diplomske naloge;

Podatki

Jezik: Slovenski jezik
Leto izida:
Tipologija: 2.11 - Diplomsko delo
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
Založnik: [G. Možina]
UDK: 547.81(043.2)
COBISS: 124507651 Povezava se bo odprla v novem oknu
Št. ogledov: 30
Št. prenosov: 9
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Angleški jezik
Sekundarni naslov: Reaction conditions influence on synthesis of different 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones as versatile building blocks of pericyclic reactions
Sekundarni povzetek: In this diploma work I present the synthesis of some 2H-pyran-2-ones and their conversion in the Diels–Alder reaction. 2H-Pyran-2-ones are aromatic organic molecules that naturally form compounds in many organisms, but in organic chemistry they are mainly very useful synthetic intermediates. Their synthesis in this work was carried out by the so-called one-pot synthesis method, in which all reactions are done without isolation of the intermediates. The products obtained by the method are pure and have rarely required further purification. The synthesized 3-benzoylamino-6-(2-thienyl)-2H-pyran-2-one was used as a diene in the Diels–Alder reaction (also known as [4+2] cycloaddition) with maleic anhydride under reflux to give the bicyclo[2.2.2.2]octene product. 5,6-Disubstituted 3-benzoylamino-2H-pyran-2-one was subjected to removal of the protecting group by hydrolysis of the amide bond. The resulting amine is not very stable, so a new protecting group using cyclopropanecarbonyl chloride was introduced. All the products synthesized were characterized by appropriate analytical methods (IR spectroscopy, TLC chromatography).
Sekundarne ključne besede: 2H-pyran-2-one;Diels-Alder reaction;one-pot synthesis;maleic anhydride;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Vrsta dela (COBISS): Diplomsko delo/naloga
Študijski program: 1000374
Konec prepovedi (OpenAIRE): 1970-01-01
Komentar na gradivo: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, VSŠ Kemijska tehnologija
Strani: 21 str.
ID: 16336558