Novi derivati benzazola: sinteza i strukturna karakterizacija

undergraduate thesis

• Title (english): The novel benzazole derivatives: synthesis and structural characterization
• Author: Kristina Olujić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Silvana Raić-Malić (član povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-09-23, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata benzimidazola (4-6) i benzotiazola (7-10) supstituiranih s 1,2,3-triazolom te njihova strukturna karakterizacija 1H i 13C-NMR spektroskopijom. 4-O-propargilbenzaldehid (1) pripravljen je reakcijom O-alkiliranja
4-hidroksibenzaldehida potpomognutom mikrovalnim zračenjem s propargil-bromidom u suhom etanolu uz K2CO3 kao bazu. Derivati benzimidazola (2) i benzotiazola (3) s terminalnom alkinilnom skupinom sintetizirani su reakcijom kondenzacije
4-klorbenzen-1,2-diamina ili 2-aminotiofenola s 4-O-propargilbenzaldehidom (1) u DMF-u uz oksidans Na2S2O5. Bakrom kataliziranom klik reakcijom O-propargiliranog derivata benzimidazola (2) s odgovarajućim azidobenzenom u kugličnom mlinu pripremljeni su
1,4-disupstituirani derivati benzimidazola (4- 6). Derivati benzotiazola supstituirani s
1,2,3-triazolom (7-10) sintetizirani su mehanokemijskom klik reakcijom O-propragiliranog derivata benzotiazola (3) i različito supstituiranih aromatskih azida. Strukture svih novopripravljenih spojeva potvrđene su 1H i 13C-NMR spektroskopijom.

Abstract (english)

This work presents synthesis of novel benzimidazole (4-6) and benzothiazole (7-10) derivatives substituted with 1,2,3-triazole and their structural characterization by 1H and
13C-NMR spectroscopy. 4-O-propargylbenzaldehide (1) was prepared by O-alkylation reaction 4-hydroxybenzaldehyde under microwave irradiation with propargyl bromide in dry ethanol with K2CO3 as a base. Benzimidazole (2) and benzothiazole (3) derivatives with terminal alknyl group were synthesized by condensation reaction of
4-chlorobenzene-1,2-diamine or 2-aminothiophenol with 4-O-propargylbenzaldehyde (1) in DMF with Na2S2O5 as oxidant. Copper-catalyzed click reaction of O-propargylated benzimidazole derivative (2) with the corresponding azidobenzene in a ball mill were prepared 1,4-disubstituted benzimidazole derivatives (4-6). Benzothiazole derivatives substituted with 1,2,3-triazole (7-10) were synthesized by mechanochemical click reaction of O-propragylated benzothiazole derivative (3) and variously substituted aromatic azides. Structures of all newly prepared compounds were confirmed by 1H and 13C-NMR spectroscopy.

• Keywords: benzimidazol; benzotiazol; 1 2 3-triazol; klik kemija; mehanokemija
• Keywords (english): benzimidazole; benzothiazole; 1 2 3-triazole; click chemistry; mechanochemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:436758
• 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: 2023-05-08 09:04:58