diplomsko delo
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: |
2022 |
Tipologija: |
2.11 - Diplomsko delo |
Organizacija: |
UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo |
Založnik: |
[G. Možina] |
UDK: |
547.81(043.2) |
COBISS: |
124507651
|
Št. ogledov: |
30 |
Št. prenosov: |
9 |
Ocena: |
0 (0 glasov) |
Metapodatki: |
|
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 |