Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije

undergraduate thesis

• Title (english): Synthesis of 2,6-disubstituted benzothiazole derivatives using mechanochemistry
• Author: Antea Posavec
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Marijana Hranjec (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-07-05, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih 2-aril-6-cijanobenzotiazolnih derivata kao potencijalnih biološki aktivnih molekula. Za pripravu ciljanih spojeva 5a‒9a, 5b–9b, 5c–9c korištena je ekološki prihvatljiva mehanokemijska sinteza. Potrebni intermedijeri priređeni su višestupnjevitom sintezom. Sinteza fenolnih derivata benzotiazola (4a‒4c) provedena je reakcijom kondenzacije bis(2-amino-5-cijanofenil)disulfida 3 s odgovarajućim benzaldehidima u ekološki prihvatljivom otapalu glicerolu. Bis(2-amino-5-cijanofenil)disulfid 3 priređen je iz 4-amino-3-tiocijanatobenzonitrila 2 reakcijom reduktivne dimerizacije s natrijevim sulfidom u etanolu i vodi, dok je 4-amino-3-tiocijanatobenzonitril 2 priređen reakcijom supstitucije iz 4-aminobenzonitrila 1 i kalijeva tiocijanata uz brom u ledenoj octenoj kiselini. Ciljani 2,6-disupstituirani derivati benzotiazola (5a‒9a, 5b–9b, 5c–9c) priređeni su O-alkiliranjem fenolnih derivata benzotiazola (4a‒4c) s odgovarajućim alkil-halogenidima. Strukture novosintetiziranih derivata potvrđene su spektroskopijom 1H i 13C NMR.

Abstract (english)

In this work synthesis of novel 2-aryl-6-cyanobenzothiazoles as potential bioactive molecules is described. For the preparation of target compounds 5a‒9a, 5b–9b, 5c–9c environmentally friendly mechanochemical synthesis was used. Required intermediates were prepared by multistep synthetic pathway. Phenolic benzothiazole derivatives (4a‒4c) were obtained by condensation of bis(2-amino-5-cyanophenyl)disulphide 3 with corresponding benzaldehydes in green solvent glycerol. Bis(2-amino-5-cyanophenyl)disulphide 3 was prepared by base-promoted reductive dimerization of 4-amino-3-thiocyanatobenzonitrile 2 with sodium sulphide in ethanol / water, while 4-amino-3-thiocyanatobenzonitrile 2 was prepared from 4-aminobenzonitrile 1 and potassium thiocyanate with bromine in acetic acid via substitution reaction. Targeted 2,6-disubstituted benzothiazole derivatives (5a‒9a, 5b–9b, 5c–9c) were prepared through O-alkylation of phenolic benzothiazole derivatives (4a‒4c) with corresponding alkyl-halogenides. The structures of all newly synthesized compounds were confirmed by 1H NMR and 13C NMR spectroscopy.

• Keywords: cijanobenzotiazoli; organska sinteza; mehanokemija; 1H NMR spektroskopija; 13C NMR spektroskopija
• Keywords (english): cyanobenzothiazoles; organic synthesis; mechanochemistry; 1H NMR spectroscopy; 13C NMR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:664813
• 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: Open access; Embargo expiration date: 2023-09-01
• Created on: 2023-03-13 10:04:18