1,2,3-triazolni derivati benzoksazola: zelena sinteza i strukturna karakterizacija

undergraduate thesis

• Title (english): 1,2,3-triazole derivatives of benzoxazole: green synthesis and structural characterization
• Author: Maja Mandić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Kristina Tolić Čop (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-22, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je četverostupanjska sinteza 1,2,3-triazolnog derivata benzoksazola konvencionalno i metodama zelene kemije. Reakcijom kondenzacije 4-hidroksibenzaldehida i 2-aminofenola sintetizirana je Schiffova baza 1 u najvećem iskorištenju konvencionalno
(90 %), koja je potom oksidativnom ciklizacijom prevedena u derivat benzoksazola 2 priređen u najvećem iskorištenju konvencionalno (34.9 %). Mikrovalovima potpomognutom reakcijom propargiliranja derivata benzoksazola 2 priređen je O-propargilirani derivat benzoksazola 3 u najvećem iskorištenju (42.17 %). 1,3-dipolarna cikloadicija katalizirana bakrovim(II) acetatom O-propargiliranog derivata 3 i azidoetilmorfolina u DES-u pokazala se najučinkovitijom
(37.6 %) u sintezi 1,2,3-triazolnog derivata benzoksazola 4. Strukturna karakterizacija spojeva provedena je spektroskopijom 1H- i 13C-NMR.

Abstract (english)

This paper describes the four-step synthesis of 1,2,3-triazole derivative of benzoxazole by conventional and green synthetic methods. The condensation reaction of 4-hydroxybenzaldehyde and 2-aminophenol gave Schiff base 1 in the highest yield by conventional method (90 %), which was then converted by oxidative cyclization reaction into a benzoxazole derivative 2 prepared in the highest yield under conventional conditions
(34.9 %). O-propargylated benzoxazole derivative 3 was synthesised in the highest yield (42.17 %) by microwave-assisted propargylation reaction of benzoxazole derivative 2.
1,3-dipolar cycloaddition reaction of O-propargylated derivative 3 and azidoethylmorpholine in DES catalyzed by copper(II) acetate proved to be the most effective (37.6 %) in the synthesis of the 1,2,3-triazole derivative of benzoxazole 4. Structural characterization of compounds was carried out by 1H- and 13C-NMR spectroscopy.

• Keywords: benzoksazol; 1 2 3-triazol; klik kemija; zelena kemija
• Keywords (english): benzoxazole; 1 2 3-triazole; click chemistry; green chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:107243
• 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: Materials Science and Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-11-30 13:40:38