Sinteza i funkcionalizacija epoksidnog derivata benzobiciklo[3.2.1]oktadienskog fotoprodukta

master's thesis

• Title (english): Synthesis and functionalization of the epoxide derivatives of benzobicyclo[3.2.1]octadiene photoproduct
• Author: Ramiza Ahmetović
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Sanja Lučić Blagojević (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-06-26, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U cilju proučavanja djelovanja epoksidnih derivata benzobiciklo[3.2.1]oktadienskog fotoprodukta na kolinesteraze, Wittigovom reakcijom sintetizirani su spojevi 1a, 1b i 1c, koji su kasnije fotokemijskom reakcijom, intramolekulskim zatvaranjem prevedeni u benzobiciklo[3.2.1]oktadienske derivate s izoliranom dvostrukom vezom (2a, 2b i 2c). U cilju funkcionalizacije dvostruke veze provedena je epoksidacija meta-klorperbenzojevom kiselinom pri čemu su dobiveni epoksidi 3a, 3b i 3c, koji se zbog velike reaktivnosti vrlo lako mogu otvoriti. Otvaranje epoksida 3a i 3c provedeno je pomoću litijevog aluminijevog hidrida u tetrahidrofuranu, a epoksida 3b pomoću natrijevog borovog hidrida u tert-butanolu i metanolu. Dobiveni alkoholi 4a i 4b prevedeni su u odgovarajuće etere (5a, 5b, 6b i 7b) pomoću odgovarajućih alkilbromida u acetonu. Novi potencijalni inhibitori kolinesteraza dobiveni su nizom reakcija i pogodni su za daljnje transformacije i funkcionalizacije.

Abstract (english)

In order to study the influence of epoxide derivatives of benzobicyclo[3.2.1]octadiene photoproducts on cholinesterase inhibitory activity, Wittig's reaction products 1a, 1b and 1c, were subsequently converted by intramolecular photoclosure to the benzobicyclo[3.2.1]octadiene derivatives with isolated double bond (2a, 2b and 2c). For the purpose of double bond functionalization, epoxidation with meta-chloroperbenzoic acid was carried out, whereby epoxides 3a, 3b and 3c, which, due to their high reactivity, can be easily opened. The opening of epoxides 3a and 3c was carried out using lithium aluminum hydride in tetrahydrofuran and epoxide 3b with sodium borohydride in tert-butanol and methanol. The alcohols 4a and 4b obtained were converted to the corresponding ethers (5a, 5b, 6b and 7b) by the appropriate alkylbromide in acetone. New potential cholinesterase inhibitors are obtained by a series of reactions and are suitable for further transformation and functionalization.

• Keywords: alkoholi; benzobiciklo[3.2.1]oktadieni; epoksidi; eteri; fotokemija; otvaranje epoksidnog prstena; spektroskopija
• Keywords (english): alcohols; benzobicyclo[3.2.1]octadienes; epoxides; ethers; photochemistry; epoxide ring opening; spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:713460
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2022-02-15 13:31:19