Funkcionalizacija 5-(4-klorstiril)oksazola i 8-klornafto[1,2-d]oksazola Buchwald-Hartwigovom aminacijom benzilnim aminima

master's thesis

• Title (english): Functionalization of 5-(4-chlorostyryl)oxazole and 8-chloronaphtho[1,2-d]oxazole by Buchwald-Hartwig amination using benzylic amine
• Author: Josipa Hodak
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Ivana Šagud (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-07-12, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U cilju nastavka proučavanja biološke aktivnosti 5-(ariletenil)oksazola razvijena je sinteza novih amino-supstituiranih derivata (2-17). Oni u svojoj strukturi imaju oksazolsku podjedinicu i amino-skupinu, koje su odgovorne za farmakološku aktivnost tih spojeva. Buchwald-Hartwigova reakcija aminacije korištena je za sintezu ove serije novih spojeva upotrebom niza različitih benzilnih-amina, piridinskih-amina i furfurilni-amin. Ispitano je nekoliko različitih uvjeta ove reakcije te je utvrđen najbolji put, koji vodi nastanku navedenih produkata s vrlo dobrim iskorištenjem. Dobiveni produkti su uspješno izolirani i pročišćeni kolonskom kromatografijom nakon čega su u potpunosti spektroskopski opisani. Jedan od dobivenih derivata, spoj 2, podvrgnut je fotokemijskoj reakciji na 350 nm kako bi se pripravila nova biciklička struktura koja u sebi ima i amino-skupinu. Ovim fotokemijskim putem sintetiziran je N-benzilnafto[1,2-d]oksazol-8-amin (18) s vrlo dobrim iskorištenjem. Dobiveni produkt je uspješno izoliran kolonskom kromatografijom. Polazni spoj 5-(4-klorstiril)oksazol (1) kao i svi njegovi produkti 2-17 i fotoprodukt 18 okarakterizirani su modernim spektroskopskim metodama (jednodimenzionalni i dvodimenzionalni NMR, UV i IR) te prevedeni u kloridne soli radi povećanja vodotopivosti i daljih ispitavanja biološke aktivnosti. Novi spojevi pogodni su i za daljnje transformacije i funkcionalizacije.

Abstract (english)

In order to continue the study of the biological activity of 5-(arylethenyl)oxazole the synthesis of new amino-substituted derivatives (2-17) have been developed. In their structure these compounds have the oxazole moiety and an amino group which are responsible for the pharmacological activity. New series of compounds (2-17) were synthesized by Buchwald-Hartwig amination using a range of different benzyl-amines, pyridine amines and furfurylamine. A number of different conditions for this reaction were examined and the best way which leads to the appearance of these products with very good yields has been determined. The resulting products were successfully isolated and purified by column chromatography and spectroscopically described. One of the obtained derivatives, compound 2, has been exposed to photochemical reaction at 350 nm to provide a new bicyclic structure that also contains the amino group. N-benzylnaphto[1,2-d]oxazol-8-amine (18) was synthesized in this photochemical method with a very good yield. The resulting product was successfully isolated by column chromatography. The starting compound 5-(4-chlorostyryl)oxazole (1) as well as all products 2-17 and photoproduct 18 were characterized by modern spectroscopic methods (one-dimensional and two-dimensional NMR, UV and IR) and translated into a chloride salt to enchance water solubility and enable futher biological activity testing. New compounds are suitable for further transformation and functionalization.

• Keywords: Buchwald-Hartwigova aminacija; oksazoli; amini; fotokemija; spektroskopija
• Keywords (english): Buchwald-Hartwig amination; oxazoles; amines; photochemistry; spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:887083
• 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: 2020-06-04 12:03:58