Sinteze 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov, pretvorbe v 3-acilamino derivate ter nadaljnje cikloadicije do biciklo[2.2.2]oktenov

diplomsko delo

Luka Zobec (Author), Krištof Kranjc (Mentor)

Abstract

V okviru diplomskega dela sem izvedel sinteze štirih 5,6-disubstituiranih 3-benzoilamino-2H-piran-2-onov po znani "one-pot" oz. enolončni dvostopenjski metodi. Iz njih sem s segrevanjem pod kislimi pogoji poskušal odstraniti benzoilno zaščitno skupino na 3-aminski skupini. Derivate s prosto 3-aminsko skupino sem ponovno zaščitil s kislinskima kloridoma (sukcinil klorid in klorobenzoil kloridom). Pri zaščiti s sukcinil kloridom sem uspel sintetizirati in izolirati dvojni 2H-piran-2-on (kjer sta dva obroča povezana z amidnim mostičkom). Na izoliranih 2H-piran-2-onih sem nato izvedel Diels–Alderjeve cikloadicije z maleinanhidridom, pri čemer sem sintetiziral dvojne biciklo[2.2.2]oktenske adukte. Te sem v nadaljevanju modificiral s piridin-2-karbohidrazidom, piridin-3-karbohidrazidom in hidrazin hidratom. Produkt s hidrazin hidratom sem še dodatno modificiral z [1,1'-difenil]-4-karbonil kloridom.

Keywords

2H-piran-2-oni;biciklo[2.2.2]okteni;cikloadicije;Diels-Alderjeva reakcija;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2023
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[L. Zobec]
UDC:	547.81(043.2)
COBISS:	167129859
Views:	49
Downloads:	9
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Syntheses of 5,6-disubstituted 3-benzoylamino-2H-pyran2-ones, conversions to 3-acylamino derivatives and further cycloadditions to bicyclo[2.2.2]octenes
Secondary abstract:	In my diploma work, I carried out syntheses of four 5,6-disubstituted 3-benzoylamino-2H-pyran-2-ones using the well-known "one-pot" two-step method. On the isolated products I attempted to remove the benzoyl protection group from the 3-amino group by heating under acidic conditions. These derivates having free 3-amino group were further reacted with two acid chlorides (succinyl chloride and chlorobenzoyl chloride). In the case of succinyl chloride, I succeeded in synthesizing and isolating a double 2H-pyran-2-one (having two rings connected with an amide bridge). I then performed Diels–Alder cycloadditions with maleic anhydride on the isolated 2H-pyran-2-ones, synthesizing bicyclo[2.2.2]octene adducts. Further on, I modified these with pyridine-2-carbohydrazide, pyridine-3-carbohydrazide and hydrazine hydrate. The hydrazine hydrate product was additionally modified with [1,1'-diphenyl]-4-carbonyl chloride.
Secondary keywords:	2H-pyran-2-ones;Diels-Alder cycloaddition;bicyclo[2.2.2]octenes;Organska sinteza (kemija);Pirani;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:	32 str.
ID:	19888208