Sinteza i spektroskopska karakterizacija novih 3-furostilbenskih oksima

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of new 3-furostilbene oximes
• Author: Ema Đurčević
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-07-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Organofosforni spojevi predstavljaju veliku prijetnju čovječanstvu jer mogu uzrokovati akutno trovanje tako da ireverzibilno inhibiraju acetilkolinesterazu, enzim koji je ključan u održavanju životnih funkcija. U cilju pronalaska potencijalnih reaktivatora inhibiranih kolinesteraza organofosfatima, sintetizirani su novi oksimski derivati 3-furilnih stilbena 7-9. Sinteza se provela nizom od tri reakcije. Prva reakcija je Wittigova reakcija s fosfonijevom soli, kojom nastaju alkeni, odnosno 3-furostilbeni 1-3. Sintetizirani su metilni, klorovi i cijano-derivati. Reakcijom nastaje smjesa cis- i trans-alkena, koja je uspješno razdvojena. Sljedeća reakcija koja se provodila je reakcija Vilsmeierovog formiliranja, gdje su se Wittigovi produkti prevodili u aldehide 4-6. Formilna skupina ulazi u preferirani položaj 2 na furanskom prstenu. Na kraju, provela se reakcija prevođenja aldehida u ciljne oksimske strukture 7-9. Dobiveni su syn- i anti- izomeri pojedinih cis- i trans-oksima. Svi dobiveni spojevi pročišćeni su i izolirani kolonskom kromatografijom na silikagelu. Svi sintetizirani izomeri okarakterizirani su spektroskopskim metodama. Koristile su se jednodimenzionalne 1H i 13C NMR tehnike, a za neke izomere i dvodimenzionalne tehnike.

Abstract (english)

Organophosphate compounds present a great threat to the humanity since they can cause acute poisoning so that they irreversibly inhibit acetylcholinesterase, an enzyme which is crucial in maintaining vital functions. As a goal of finding potential reactivators of inhibited cholinesterase by organophosphates, the new oxime derivates of 3-furostilbenes 7-9 are synthesized. The synthesis was conducted in sequence of three reaction steps. The first reaction was Wittig reaction with phosphonium salt and corresponding aldehyde, by which the alkenes, 3-furostilbenes 1-3, are obtained as methyl, chlorine and cyano-derivatives. The mixtures of cis- and trans-alkenes synthesized by the reaction were successfully separated. The next reaction step that was conducted is the reaction of Vilsmeier formylation, where Wittig`s products were converted into aldehydes 4-6. Formyl group enters into preferred position 2 on the furan ring. At the end, the reaction of translating aldehydes into oximes structures 7-9 was conducted. Syn- and anti-isomers of individual cis- and trans-oximes are gained. All the synthesized compounds are purified and isolated using column chromatography on the silica gel. All the synthesized isomers are characterized by spectroscopic methods. One-dimensional 1H and 13C NMR techniques as well as for some isomers two-dimensional techniques were used.

• Keywords: kolinesteraze; organofosfati; oksimi; 3-furostilbeni; Wittigova reakcija; Vilsmeierovo formiliranje
• Keywords (english): cholinesterase; organophosphate compounds; oximes; 3-furostilbenes; Wittig reaction; Vilsmeier formylation
• Language: croatian
• URN:NBN: urn:nbn:hr:149:684488
• Study programme: Title: Applied Chemistry - Undergraduate 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: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-03-27 12:43:42