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

Zobec, Luka (author), Kranjc, Krištof (mentor)

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.

• Language: Slovenian
• Keywords: 2H-piran-2-oni, Diels–Alderjeva cikloadicija, biciklo[2.2.2]okteni
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-149151
• COBISS.SI-ID: 167129859
• Publication date in RUL: 04.09.2023

Secondary language

• Language: English
• 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

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.

• Keywords: 2H-pyran-2-ones, Diels–Alder cycloaddition, bicyclo[2.2.2]octenes