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

master's thesis

• Title (english): Novel 1,2,3-triazole derivatives of benzoxazole and benzimidazole: synthesis and structural characterization
• Author: Jurja Vukovinski
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Ivana Sokol (član povjerenstva)
• Committee member: Dajana Kučić Grgić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-07-12, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih 1,2,3-triazolnih derivata benzoksazola i benzimidazola klik-reakcijom, njihova strukturna karakterizacija spektroskopijom NMR te analiza in silico. Reakcijom ciklokondenzacije odgovarajućih aminofenola pripravljeni su derivati benzo[d]oksazol-2-tiola 2 i 3 koji su reakcijom kondenzacije s 2-(klormetil)-1H-benzo[d]imidazolom 1 prevedeni u hibride benzimidazola i benzoksazola 4 i 5 premoštene tiometilenskom spojnicom. Reakcijom N-propargiliranja dobivenih hibrida pripravljeni su alkilirani derivati 7 i 8 koji su 1,3-dipolarnom cikloadicijom kataliziranom bakrom s prethodno pripravljenim azidima 9–16 prevedeni u ciljane 1,2,3-triazolne derivate benzimidazola i benzoksazola 18–31. Strukturna karakterizacija sintetiziranih spojeva provedena je spektroskopijom 1H- i 13C-NMR, dok su biološka djelovanja predviđena PASS analizom in silico.

Abstract (english)

This paper describes the synthesis of novel 1,2,3-triazole derivatives of benzoxazole and benzimidazole by click reaction, their structural characterization using NMR spectroscopy and in silico analysis. Derivatives of benzo[d]oxazole-2-thiol 2 and 3 were prepared through cyclization of appropriate aminophenols, followed by condensation with 2-(chloromethyl)-1H-benzo[d]imidazole 1 to obtain hybrids of benzimidazole and benzoxazole 4 and 5 bridged by a thiomethylene linker. N-propargylation reaction of the resulting hybrids yielded alkylated derivatives 7 and 8, which underwent copper catalyzed 1,3-dipolar cycloaddition with prepared azides 9–16 to yield targeted 1,2,3-triazole derivatives of benzimidazole and benzoxazole 18–31. Structural characterization of novel compounds was carried out by 1H- and 13C-NMR spectroscopy, while biological activity was predicted by in silico PASS analysis.

• Keywords: benzoksazol; benzimidazol; klik-kemija
• Keywords (english): benzoxazole; benzimidazole; click chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:286061
• 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; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: Hrvatska zaklada za znanost; Funding stream: Research Projects
• Study programme: Title: Applied Chemistry - Graduate 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: graduate; Academic / professional title: sveučilišni/a magistar/magistra primijenjene kemije (sveučilišni/a magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2026-10-01
• Created on: 2024-07-15 15:00:00