Sinteza i biološka aktivnost N-supstituiranih benzoksazola

undergraduate thesis

• Title (english): Synthesis and biological activity of N-substituted benzoxazole
• Author: Dominik Milanović Litre
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Committee member: Ivana Sokol (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-09-11, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata 2-benzoksazolinona u svrhu ispitivanja njihove biološke aktivnosti. Reakcijom nukleofilne supstitucije 5-supstituiranih 2-aminofenola i
1,1`-karbonildiimidazolom u tetrahidrofuranu pripravljeni su 5-supstituirani benzo[d]oksazol-2-oni (1a–c). 5-supstituirani N-propargilbenzo[d]oksazol-2-oni (2a–c) priređeni su reakcijom propargiliranja 5-supstituiranih benzo[d]oksazol-2-ona (1a–c) s propargil-bromidom u acetonu uz prisustvo kalijeva karbonata kao baze. Različito supstituirani 1-azidobenzeni (3a–e) potrebni za klik reakciju sintetizirani su reakcijom odgovarajućih supstituiranih anilina s natrijevim azidom u vodenoj otopini natrijeva nitrita. Huisgenovom 1,3-dipolarnom cikloadicijom kataliziranom bakrom N-propargiliranih benzoksazolona (2a–c) i odgovarajućih azidobenzena (3a–e) dobiveni su ciljani derivati benzoksazolinona supstituirani 1,2,3-triazolnim prstenom (4a–8c). Strukture sintetiziranih spojeva potvrđene su spektroskopijom 1H- i 13C-NMR.

Abstract (english)

This paper describes the synthesis of new 2-benzoxazolinone derivatives with the aim of evaluating their biological activity. 5-substituted benzo[d]oxazol-2-ones (1a–c) were obtained by nucleophylic reaction of 5-substituted 2-aminophenols with 1,1`-carbonyldiimidazole in the tetrahydrofuran. 5-substituted N-propargylbenzo[d]oxazol-2-ones (2a–c) were prepared by the propargylation reaction of 5-substituted benzo[d]oxazol-2-ones (1a–c) with propargyl bromide in the acetone and in the presence of potassium carbonate as a base. Differently substituted 1-azidobenzenes (3a–e) were synthesized using corresponding substituted anilines with sodium azide in an aqueous solution of sodium nitrite. Finally, targeted benzoxazolinone derivatives substituted with 1,2,3-triazole ring (4a–8c) were prepared by copper catalyzed Huisgen's 1,3-dipolar cycloaddition reaction of N-propargylated benzoxazolones (2a–c) and corresponding azidobenzenes (3a–e). The structures of the synthesized compounds were confirmed by 1H- and 13C-NMR spectroscopy.

• Keywords: 2-benzoksazolon; biološka aktivnost; Huisgenova 1 3-dipolarna cikloadicija; 1 2 3-triazol; klik-kemija
• Keywords (english): 2-benzoxazolone; biological activity; Huisgen 1 3-dipolar cycloaddition; 1 2 3-triazole; click chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:708514
• Project: Number: IP-2022-10-9420; Title: Novi N‐heterocikli i njihovi kompleksi s antitumorskim i antitripanosomskim djelovanjem; Title: Novel N-heterocycles and their metal complexes with anticancer and antitrypanosomal activity; Acronym: NHet&MetCom Project; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: Hrvatska zaklada za znanost; Funding stream: Research Projects
• 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: 2026-10-01
• Created on: 2024-11-14 10:58:49