Sinteza i strukturna karakterizacija 1,2-disupstituiranih derivata benzimidazola

undergraduate thesis

• Title (english): Synthesis and structural characterization of 1,2-disubstituted benzimidazole derivatives
• Author: Maria Jeftimija
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Silvana Raić-Malić (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-07-07, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata benzimidazola supstituiranih u položaju 1 triazolnim supstituentima i u položaju 2 arilnim supstituentima (9-16). U prvom stupnju sinteze su pripravljeni kao ključni prekursori arilbenzimidazoli 1 i 2 reakcijom ciklizacije odgovarajućih 1,2-diaminobenzena i benzaldehida koji su potom u sljedećem stupnju reakcije alkiliranja prevedeni u N-propargilirane derivate benzimidazola 3 i 4. U zadnjem stupnju je Huisgenovom 1,3-dipolarnom cikloadicijom propargiliranih derivata benzimidazola (3 i 4) s odgovarajućim priređenim azidima (5-8), uz Cu(Ac)2 kao katalizator; u položaj
N-1 benzimidazola uveden 1,2,3-triazolni prsten. Strukture svih novopripravljenih derivata benzimidazola potvrđene su spektroskopijom 1H i 13C-NMR.

Abstract (english)

This paper describes the synthesis of new benzimidazole derivatives substituted in position 1 with triazole substituents and in position 2 with aryl substituents, (9-16). In the first stage of synthesis, arylbenzimidazoles were prepared as key precursors 1 and 2 by the cyclization reaction of the corresponding 1,2-diaminobenzene and benzaldehyde, which were then converted into N-propargylated derivates of benzimidazole 3 and 4 in the next stage of the alkylation reaction. In the last stage, through Huisgen 1,3-dipolar cycloaddition of propargylated benzimidazole derivatives (3 and 4) with the corresponding prepared azides (5-8), using Cu(Ac)2 as a catalyst, a 1,2,3-triazole ring was introduced at the N-1 position of benzimidazole. The structures of all newly synthesized benzimidazole derivatives were confirmed by spectroscopy 1H and 13C-NMR.

• Keywords: benzimidazol; 1 2 3-triazol; klik reakcija; Huisgenova 1 3-dipolarna cikloadicija
• Keywords (english): benzimidazole; 1 2 3-triazole; click reaction; Huisgen 1 3-dipolar cycloaddition reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:234060
• 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: 2025-09-30
• Created on: 2023-07-25 14:03:58