Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije

master's thesis

• Title (english): Synthesis of new benzoxazole derivatives using the concept of molecular hybridization
• Author: Sara Prenc
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Andrijana Meščić Macan (član povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-09-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata benzoksazola konceptom molekulske hibridizacije bakrom kataliziranom klik reakcijom u niskotemperaturnom eutektičkom otapalu (DES) te njihova strukturna karakterizacija 1H- i 13C-NMR spektroskopijom. Kondenzacijom odgovarajuće supstituiranih 4-hidroksibenzaldehida i 2-aminofenola sintetizirani su derivati Schiffovih baza 1-6 koji su nadalje ciklizacijom prevedeni u 2-arilbenzoksazole. Mikrovalovima potpomognutom reakcijom propargiliranja 2-arilbenzoksazola 7-12 s propargil-bromidom uz kalijev karbonat kao bazu sintetizirani su O-propargilirani derivati benzoksazola 13-18. Odgovarajući azidi 19-21 za klik reakciju pripravljeni su reakcijom 1-(2-kloretil)pirolidin-,
1-(2-kloretil)piperidin- i 1-(2-kloretil)morfolin-hidroklorida s natrijevim azidom. Reakcijom O-propargiliranih derivata benzoksazola 13-18 s odgovarajućim azidima 19-21
1,3-dipolarnom cikloadicijom kataliziranom bakrovim (I) jodidom u niskotemperaturnom eutektičkom otapalu (DES) kolin klorid (ChCl)/glicerol (1:2) dobiveni su ciljani 1,2,3-triazolni derivati benzoksazola 22-36 u iskorištenjima 21 - 83 %. Klik reakcijama derivata benzoksazola 13 s aromatskim azidima u eutektičkom otapalu ChCl/glicerol (1:2) dobiveni su 1,2,3-triazolni derivati benzoksazola 39 i 40 u dobrim iskorištenjima.

Abstract (english)

This paper describes the synthesis of new benzoxazole derivatives by molecular hybridization via copper catalyzed click reactions in a deep eutectic solvent (DES) and their structural characterization by 1H- and 13C-NMR spectroscopy. Condensation of substituted 4-hydroxybenzaldehydes and 2-aminophenols yielded the corresponding Schiff bases 1-6 which were further converted to the corresponding 2-arylbenzoxazoles 7-12 by cyclization. O-propargylated benzoxazole derivatives 13-18 were synthesized by propargylation of the obtained 2-arylbenzoxazoles with propargyl bromide and potassium carbonate as the base. In a reaction of N-chloroethylpyrrolidine, N-chloroethylpiperidine and N-chloroethylmorpholine hydrochloride with sodium azide, the corresponding azides 19-21 were prepared. Reaction of O-propargylated benzoxazole derivatives with the corresponding azides by
1,3-dipolar copper-catalyzed cycloaddition in ChCl/glycerol (1:2) based DES yielded the target 1,2,3-triazole benzoxazole derivatives 22-36 in yields 21 - 83 %. Click reactions of benzoxazole derivative 13 with aromatic azides carried out in the ChCl/glycerol (1:2) DES yielded 1,2,3-triazole benzoxazole derivatives 39 i 40 in good yields.

• Keywords: benzoksazol; 1 2 3-triazol; klik reakcija; niskotemperaturna eutektička otapala; DES; ChCl/glicerol
• Keywords (english): benzoxazole; 1 2 3-triazole; click reaction; deep eutectic solvents; DES; ChCl/glycerol
• Language: croatian
• URN:NBN: urn:nbn:hr:149:986071
• 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: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-04-13 12:12:51