Sinteza i karakterizacija novih benzilnih derivata heterostilbena

undergraduate thesis

• Title (english): Synthesis and characterization of new benzyl derivatives of heterostilbenes
• Author: Maja Ratajec
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Marijana Kraljić Roković (član povjerenstva)
• Committee member: Jozefina Katić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-07-09, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U svrhu nastavka proučavanja biološke aktivnosti heterostilbena kojima je jedna benzenska jezgra zamijenjena heterocikličkom jezgrom, razvijena je sinteza novih amino-supstituiranih derivata 2-stiriltiofena (2-6). U strukturi imaju tiofensku podjedinicu i amino-skupinu, odgovorne za farmakološku aktivnost tih spojeva. Wittigovom reakcijom pripremljen je početni spoj 1 koji nastaje u obliku smjese cis- i trans-izomera te se ta smjesa podvrgla aminacijama. Reakcije sinteze tekle su Buchwald-Hartwigovim mehanizmom uz različito supstituirane benzilne amine. Tijekom razvoja sinteze ispitano je nekoliko reakcijskih uvjeta te je utvrđen postupak koji dovodi do nastanka spojeva s najvećim iskorištenjima. Reakcije su provedene u prisutnosti paladijevog Pd(OAc)2 katalizatora, otapala 1,4-dioksana te liganada XPhosa i BrettPhosa. Dobiveni su produkti izolirani kolonskom kromatografijom na stupcu silikagela. Svi su spojevi okarakterizirani spektroskopskim metodama (1H NMR i MS).

Abstract (english)

In the interest of further studying the biological activity of heterostilbenes where one benzene ring has been substituted with a heterocyclic ring, synthetic route for new amino substituted derivatives of 2-styrylthiophenes (2-6) has been developed. In their structure these compounds bear the thiophene moiety and an amino group which display pharmacological activity. Wittig reaction was used for obtaining the starting compound 1 obtained as a mixture of cis- and trans-isomers that was subjected to aminations. The synthesis reactions was proceeded according to the Buchwald-Hartwig mechanism with varying benzylamines. Developing the synthetic route some reaction conditions were tested and the procedure which insured formation of products with the highest yield was established. Reactions were carried out in the presence of palladium Pd(OAc)2 catalyst,1,4-dioxane as solvent and ligands XPhos and BrettPhos. Synthesized products were isolated by column chromatography on a silica gel column. All compounds were characterized by spectroscopic methods (1H NMR, MS).

• Keywords: amini; Buchwald-Hartwigova aminacija; spektroskopija; tiofeni; Wittigova reakcija
• Keywords (english): amines; Buchwald-Hartwig amination; spectroscopy; thiophenes; Wittig reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:916334
• 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: 2023-05-08 14:05:32