Novi derivati benzoksazola: sinteza i strukturna karakterizacija

undergraduate thesis

• Title (english): The novel benzoxazole derivatives: synthesis and structural characterization
• Author: Antonija Jelčić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-09-17, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata benzoksazola i njihova strukturna karakterizacija 1H- i 13C-NMR spektroskopijom. Reakcijom 4-hidroksibenzaldehida i odgovarajućih alkilirajućih reagenasa pripravljeni su O-alkilirani benzaldehidi (1-6) kao prekurosri koji su zatim s različito supstituiranim ortho-aminofenolima prevedeni u derivate Schiffovih baza (7-19). Oksidativnom ciklizacijom Schiffovih baza sintetizirani su derivati benzoksazola (20-32). Mikrovalno potpomognutim O-propargiliranjem
4-(5-metoksibenzo[d]oksazol-2-il)fenola (32) s propargil-bromidom uz kalijev karbonat kao bazu sintetiziran je 5-metoksi-2-(4-(prop-2-in-1-iloksi)fenil)benzo[d]oksazol (33) koji je potom klik reakcijom 1,3-dipolarne cikloadicije katalizirane bakrovim(I) jodidom s prethodno dobivenim azidima (34-36) preveden u 1,2,3-triazolne derivate benzoksazola (37-39). Strukture svih novopripravljenih derivata benzoksazola potvrđene su 1H- i 13C-NMR spektroskopijom.

Abstract (english)

This work describes the synthesis of new benzoxazole derivatives and their structural characterization by 1H- and 13C-NMR spectroscopy. The reaction of 4-hydroxybenzaldehyde and the corresponding alkylating reagents prepared O-alkylated benzaldehydes (1-6) as precursors which were then converted into derivatives of Schiff bases (7-19) with variously substituted ortho-aminophenols. Oxidative cyclization of Schiff bases benzoxazole derivatives (20-32) were synthesized. Microwave-assisted O-propargylation of 4-(5-methoxybenzo[d] oxazol-2-yl)phenol (32) with propargyl bromide using potassium carbonate as a base synthesized 5-methoxy-2-(4-(prop-2)-in-1-yloxy)phenyl)benzo[d]oxazole (33) which was then converted to 1,2,3-triazole benzoxazole derivatives (37-39) by the click reaction of
1,3-dipolar cycloaddition catalyzed by copper (I) iodide with previously obtained azides (34-36). The structures of all newly prepared benzoxazole derivatives were confirmed by
1H- and 13C-NMR spectroscopy.

• Keywords: benzoksazol; Schiffove baze; 1 2 3-triazol; klik reakcija; O-alkilirani benzaldehidi
• Keywords (english): benzoxazole; Schiff bases; 1 2 3-triazole; click reaction; O-alkylated benzaldehydes
• Language: croatian
• URN:NBN: urn:nbn:hr:149:364276
• Project: Number: IP-2018-01-4682; Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja; Acronym: PurBioCaPa; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• 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: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-04-04 07:31:12