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undergraduate thesis
Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2022. urn:nbn:hr:149:664813
Posavec, Antea
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Posavec, A. (2022). Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:664813

Posavec, Antea. "Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2022. https://urn.nsk.hr/urn:nbn:hr:149:664813

Posavec, Antea. "Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2022. https://urn.nsk.hr/urn:nbn:hr:149:664813

Posavec, A. (2022). 'Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 04 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:664813

Posavec A. Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2022 [cited 2024 November 04] Available at: https://urn.nsk.hr/urn:nbn:hr:149:664813

A. Posavec, "Sinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:149:664813

Metadata
TitleSinteza 2,6-disupstituiranih derivata benzotiazola primjenom mehanokemije
Title (english)Synthesis of 2,6-disubstituted benzothiazole derivatives using mechanochemistry
AuthorAntea Posavec
MentorSilvana Raić-Malić (mentor)
Committee memberSilvana Raić-Malić (predsjednik povjerenstva)
Committee memberMarijana Hranjec (član povjerenstva)
Committee memberDanijela Ašperger (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2022-07-05, 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
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:664813
ProjectNumber: 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 programmeTitle: 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 resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2023-09-01
Terms of useLicence In copyright icon
Created on2023-03-13 10:04:18