Priprava novih nitro-supstituiranih derivata benzotiazola

undergraduate thesis

• Title (english): Preparation of novel nitro-substituted benzothiazole derivatives
• Author: Monika Petanjko
• 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 sklopu završnog rada provedena je mehanokemijska sinteza O-alkiliranih 6-nitro-supstituiranih derivata benzotiazola 5a‒10a, 5b‒10b, 5c‒10c, kao i sinteza potpomognuta mikrovalovima benzotiazolnih derivata supstituiranih 1,2,3-1H-triazolom 11a–11c. Ključni prekursori 4-(6-nitrobenzotiazol-2-il)fenola 4a–4c pripravljeni su u glicerolu reakcijom bis(2-amino-5-nitrofenil)disulfida 3 i odgovarajućeg supstituiranog 4-hidroksibenzaldehida. Sinteza ciljanih O-alkiliranih 6-nitro-supstituiranih benzotiazola (5a‒10a, 5b‒10b, 5c‒10c) provedena je iz odgovarajućih fenolnih derivata (4a–4c) u reakciji s određenim alkil-halogenidom u kugličnom mlinu. Sinteza 1,2,3-1H-triazolnih derivata benzotiazola 11a–11c provedena je Cu(I) kataliziranom regioselektivnom 1,3-dipolarnom cikloadicijom iz odgovarajućih terminalnih alkina benzotiazola 5a–5c i trimetilsililazida. Navedenim „klik“ reakcijama koje su provedene u mikrovalnom reaktoru nisu izolirani ciljani produkti. Strukturna i spektroskopska karakterizacija novopriređenih spojeva provedena je 1H i 13C NMR spektroskopijom.

Abstract (english)

As part of this paper, mechanochemical synthesis of O-alkylated 6-nitro-substituted benzothiazole derivatives 5a‒10a, 5b‒10b, 5c‒10c was performed, as well as microwave-assisted synthesis of benzothiazole derivatives substituted with 1,2,3-1H-triazole 11a–11c. Key intermediates 4-(6-nitrobenzothiazol-2-yl)phenols 4a–4c were prepared in glycerol by reaction of bis (2-amino-5-nitrophenyl)disulfide 3 and the corresponding substituted 4-hydroxybenzaldehyde. The synthesis of targeted O-alkylated 6-nitro-substituted benzothiazoles (5a‒10a, 5b‒10b, 5c‒10c) was performed from the corresponding phenolic derivatives (4a–4c) and alkyl halides in a ball mill. The synthesis of 1,2,3-1H-triazole derivatives of benzothiazole 11a–11c was performed by regioselective Cu(I) catalyzed 1,3-dipolar cycloaddition from the corresponding terminal alkynes of benzothiazole 5a–5c and trimethylsilylazide. These "click" reactions performed in the microwave reactor did not yield the target products. Structural and spectroscopic characterization of the newly prepared compounds was performed by 1H and 13C NMR spectroscopy.

• Keywords: benzotiazol; nitro-supstituirani benzotiazoli; mehanokemijska sinteza; 1 2 3-1H-triazoli; Huisgenova cikloadicija; „klik“ reakcija; sinteza potpomognuta mikrovalovima
• Keywords (english): benzothiazole; nitro-substituted benzothiazoles; mechanochemical synthesis; 1 2 3-1H-triazoles; Huisgen cycloaddition; „click“ reaction; microwave-assisted synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:149:171123
• 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 09:17:49