Sinteza i strukturna karakterizacija novih derivata benztiazola

undergraduate thesis

• Title (english): Synthesis and structural characterization of novel benzothiazole derivatives
• Author: Hanja Mlinar
• 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 benzotiazola primjenom mikrovalovima potpomognutih, mehanokemijskih i klik reakcija. Za sintezu derivata benzotiazola pripravljen je 4-O-propargilbenzaldehid (1) SN2 reakcijom 4-hidroksibenzaldehida i propargil-bromida uz K2CO3 kao bazu. 2-(4-(prop-2-in-1-iloksi)fenil)benzotiazol (2) priređen je ciklizacijom
4-O-propargilbenzaldehida (1) i 2-aminotiofenola u dimetilformamidu uz Na2S2O5 kao oksidacijsko sredstvo. Huisgenovom 1,3-dipolarnom cikloadicijom
2-(4-(prop-2-in-1-iloksi)fenil)benzotiazola (2) i odgovarajućih azida uz bakrov(II) acetat kao katalizator sintetizirani su 1,2,3-triazolni derivati benzotiazola (3-9). Mehanokemijske reakcije ciljanih derivata benzotiazola (3-9) provedene su u kugličnom mlinu. 1H i 13C-NMR spektroskopijom potvrđene su strukture svih novopripravljenih derivata benzotiazola.

Abstract (english)

This paper describes the synthesis of new benzothiazole derivatives using microwaveassisted, mechanochemical and click reactions. For the synthesis of benzothiazole derivatives, 4-O-propargylated benzaldehyde (1) was prepared by SN2 reaction of 4-hydroxybenzaldehyde and propargyl bromide using K2CO3 as a base.
2-(4-(prop-2-yn-1-yloxy)phenyl) benzothiazole (2) was prepared by cyclization reaction of 4-O-propargyl benzaldehyde (1) and 2-aminothiophenol in dimethylformamide with Na2S2O5 as oxidizing agent. 1,2,3-triazolyl derivatives of benzothiazole (3-9) were prepared by Huisgen 1,3-dipolar cycloaddition of 2-4-(prop-2-yn-1-yloxy)phenyl benzothiazole (2) and the corresponding azides using copper(II) acetate as catalyst. Mechanochemical reactions of the desired compounds (3-9) were performed in a ball mill. The structures of all newly prepared benzothiazole derivatives were confirmed by 1H and 13C-NMR spectroscopy.

• Keywords: benzotiazol; 1 2 3-triazol; klik reakcija; Huisgenova 1 3-dipolarna cikloadicija; mehanokemijske reakcije
• Keywords (english): benzothiazole; 1 2 3-triazole; click reaction; Huysgen 1 3-dipolar cycloaddition; mechanochemical reactions
• Language: croatian
• URN:NBN: urn:nbn:hr:149:983220
• 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 08:11:02