3-acilamino-2H-piran-2-oni in njihovi derivati kot dieni za [4+2] cikoadicije z različnimi cikličnimi elektronsko siromašnimi alkeni

diplomsko delo

Dominik Kušar (Author), Krištof Kranjc (Mentor)

Abstract

V diplomskem delu sem z enolončno sintezno metodo uspešno sintetiziral dva različno substituirana 3-benzoilamino-2H-piran-2-ona. V nadaljevanju sem, dvakrat uspešno in enkrat neuspešno, na izbranih 3-benzoilamino-2H-piran-2-onih odstranil benzoilaminsko skupino. Odščitene derivate sem nato reagiral z enojnim in dvojnim kislinskim kloridom, pri čemer sem pri slednjem uspešno izoliral sistem, kjer sta povezana dva 2H-piran-2-onska obroča. Tri izbrane 3-benzoilamino-2H-piran-2-onske derivate sem reagiral z maleinanhidridom in pri tem izoliral serijo biciklo[2.2.2]oktenskih aduktov. Na izbranem biciklo[2.2.2]oktenskem aduktu sem s hidrazin hidratom poskušal pretvoriti sukcinanhidridni obroč v N-aminosukcinimidni obroč, vendar neuspešno. V zadnjem sklopu reakcij sem izvedel reakcijo med dvema izbranima biciklo[2.2.2]oktenskima aduktoma in dvema različnima hidrazidoma.

Keywords

enolončna sinteza;cikloadicije;Diels-Alderjeva reakcija;2H-piran-2-on;biciklo[2.2.2]oktenski adukt;hidrazid;hidrazin hidrat;meleinanhidrid;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2023
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[D. Kušar]
UDC:	547.81(043.2)
COBISS:	165224195
Views:	46
Downloads:	8
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	3-Acylamino-2H-pyran-2-ones and their derivatives as dienes for [4+2] cycloadditions with various cyclic electron-deficient alkenes
Secondary abstract:	In this diploma, I successfully synthesized two differently substituted 3-benzoylamino-2H-pyran-2-ones by one-pot synthesis method. Next, I removed the benzoylamino group on selected 3-benzoylamino-2H-pyran-2-ones, twice successfully and once unsuccessfully. Then I introduced two new protecting groups on the 3-amino end of the molecule, one with an acid chloride and the other with a double acid chloride. In the latter I successfully isolated a system where two 2H-pyran-2-ones are connected. I reacted three selected 3-benzoylamino-2H-pyran-2-one derivatives with maleic anhydride and isolated a series of bicyclo[2.2.2]octene adducts. On the selected bicyclo[2.2.2]octene adducts I tried to convert the succinic anhydride ring to the N-aminosuccinimide ring with hydrazine hydrate, but without success. In the last set I performed reactions between two selected bicyclo[2.2.2]octene adducts and two different hydrazides.
Secondary keywords:	one-pot synthesis;Diels-Alder reaction;2H-pyran-2-one;bicyclo[2.2.2]octene adduct;hydrazide;hydrazine hydrate;maleic anhydride;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:	41 str.
ID:	19876318