Vpliv reakcijskih pogojev na sinteze različnih 5,6- disubstituiranih 3-benzoilamino-2H-piran-2-onov kot vsestranskih gradnikov v pericikličnih reakcijah

diplomsko delo

Gašper Možina (Author), Krištof Kranjc (Mentor)

Abstract

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).

Keywords

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

Data

Language:	Slovenian
Year of publishing:	2022
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[G. Možina]
UDC:	547.81(043.2)
COBISS:	124507651
Views:	30
Downloads:	9
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Reaction conditions influence on synthesis of different 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones as versatile building blocks of pericyclic reactions
Secondary abstract:	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).
Secondary keywords:	2H-pyran-2-one;Diels-Alder reaction;one-pot synthesis;maleic anhydride;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000374
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, VSŠ Kemijska tehnologija
Pages:	21 str.
ID:	16336558