Novi derivati 2-arilbenzoksazola: sinteza, strukturna karakterizacija i antibakterijsko djelovanje

master's thesis

• Title (english): Novel 2-aryl benzoxazole derivatives: synthesis, structural characterization and antibacterial potential
• Author: Kristina Olujić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Dajana Kučić Grgić (član povjerenstva)
• Committee member: Matija Cvetnić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata benzoksazola (26-52) te njihova strukturna karakterizacija 1H i 13C-NMR spektroskopijom. O-supstituirani derivati benzaldehida (5-7) sintetizirani su reakcijom 3-brom-4-hidroksibenzaldehida s odgovarajućim alikilirajućim agensima u acetonitrilu uz K2CO3 kao bazu. Schiffove baze (8-16) pripravljene su nukleofilnom adicijom odgovarajućih primarnih amina na karbonilni ugljik O-alkiliranih benzaldehida (5-7) u apsolutnom etanolu uz prisutnost ZnO. Intramolekulskom oksidativnom ciklizacijom Schiffovih baza (8-16) u dimetilformamidu uz prisutnost NaCN i kisika iz zraka sintetizirani su derivati benzoksazola (17-25). Ciljani alkinirani derivati benzoksazola (26-52) sintetizirani su paladijem kataliziranom Sonogashirinom reakcijom unakrsnog spajanja benzoksazola (17-25) s alifatskim i aromatskim alkinima uz trietilamin kao bazu i katalizator bis(trifenilfosfin)paladijev(II) klorid. Strukture svih novopripravljenih spojeva potvrđene su 1H i 13C-NMR spektroskopijom.

Abstract (english)

This work presents the synthesis of novel benzoxazole derivatives (26-52) and their structural characterization by 1H and 13C-NMR spectroscopy. O-substituted benzaldehyde derivatives (5-7) were synthesized by reaction of 3-bromo-4-hydroxybenzaldehyde with corresponding alkylating agents in acetonitrile with K2CO3 as a base. Schiff bases (8-16) were prepared by nucleophilic addition of corresponding primary amines to the carbonyl c,arbon of O-alkylated benzaldehydes (5-7) in absolute ethanol and in the presence of ZnO. Benzoxazole derivatives (17-25) were synthesized by intramolecular oxidative cyclization of Schiff bases (8-16) in dimethylformamide and the presence of NaCN and oxygen from the air. Targeted alkynyl benzoxazole derivatives (26-52) were synthesized by palladium-catalyzed Sonogashira cross-coupling reaction of benzoxazole derivatives (17-25) and aliphatic and aromatic alkynes with triethylamine as a base and catalyst bis(triphenylphosphine) palladium(II) chloride. The structures of all newly prepared compounds were confirmed by 1H and 13C-NMR spectroscopy.

• Keywords: benzoksazol; Schiffove baze; reakcija unakrsnog spajanja; Sonogashirina reakcija
• Keywords (english): benzoxazole; Schiff bases; cross-coupling reaction; Sonogashira reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:255010
• 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 - 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: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-03-19 18:20:11