Funkcionalizacija oksimskog derivata benzobiciklo[3.2.1]oktadiena

undergraduate thesis

• Title (english): Functionalization of oxime derivative of the benzobicyclo[3.2.1]octadiene
• Author: Ana Vukovinski
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Marijana Kraljić Roković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-07-02, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U cilju funkcionalizacije benzobiciklo[3.2.1]oktadienskog skeleta provedene su reakcije sinteze oksima i oksimskih etera. Početni oksim 2 sintetiziran je u nekoliko stupnjeva Wittigovom reakcijom te Vilsmeierovim formiliranjem, a daljnjim reakcijama supstitucije preveden je u oksimske etere 5-10. Gotovo svi dobiveni produkti imaju otvorenu furansku jezgru, osim oksimskog etera 7, čija je jezgra zatvorena, što potvrđuje 1H NMR spektar. Iskorištenje provedenih reakcija ovisi upravo o otvaranju furanskog prstena. Uočena su veća iskorištenja spojeva kod kojih je kisik, u obliku karbonilne ili hidroksilne skupine vezan na biciklički dio molekule. Oksimi i njihovi derivati sve se više koriste u medicinskim istraživanjima, prvenstveno u području inhibicije kolinesteraza, a upravo sintetizirani oksim 2 i oksimski eteri 5-10 strukturno podsjećaju na već opisane inhibitore tih enzima. Svi spojevi su okarakterizirani modernim spektroskopskim metodama, 1H NMR spektroskopijom te
IR metodom.

Abstract (english)

For the purpose of benzobicyclo[3.2.1]octadiene skeleton functionalization, oxime and oxime ethers syntheses were performed. Initial oxime 2 was synthesized in several steps by Wittig reaction and Vilsmeier formylation, and by further substitution reactions was converted into oxime ethers 5-10. Almost all the resulting products have an open furan ring, except oxime ether 7, whose ring is closed, as confirmed by the 1H NMR spectrum. The yield of the reactions depends on the opening of the furan ring. Greater yields were utilized on compounds in which the oxygen, in the form of carbonyl or hydroxyl group, is attached to the bicyclic moiety of the molecules. Oximes and their derivatives are increasingly used in medical research, primarily in the field of cholinesterase inhibition. The synthesized oxime 2 and oxime ethers 5-10 are structurally reminded of the already-described inhibitors of these enzymes. All compounds were characterized by modern spectroscopic methods,
1H NMR spectroscopy and IR method.

• Keywords: benzobiciklo[3.2.1]oktadieni; furanska jezgra; kolinesteraze; oksimi; oksimski eteri
• Keywords (english): benzobicyclo[3.2.1]octadiene; furan ring; cholinestarase; oxime; oxime ethers
• Language: croatian
• URN:NBN: urn:nbn:hr:149:931792
• 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: 2023-05-29 12:34:55