Sinteza amino-supstituiranih derivata benzotiazola

undergraduate thesis

• Title (english): Synthesis of amino-substituted benzothiazoles derivatives
• Author: Helena Mijić
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Mirjana Novak Stankov (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-18, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada bila je sinteza novih 2-amino-supstituiranih benzotiazola 5-7, te 6-amino-supstituiranih benzotiazola 13-17. Za pripravu ciljnih spojeva korištene su klasične metode organske sinteze. Sinteza 2-amino supstituiranih derivata benzotiazola provedena je reduktivnom aminacijom, kojom je dobiven spoj N-(4-(2-fenil-2-oksoetoksi)benzil)benzotiazol-2-amin 5, dok se sintezi 6-amino-susptituiranih derivata pristupilo na dva načina, reakcijom nukleofilne supstitucije i Buchwald-Hartwig-ovom reakcijom. Prvim sintetskim putem, nukleofilnom supstitucijom iz kloriranog derivata 12, nisu dobiveni ciljni spojevi 13 i 14. Provedbom Buchwald-Hartwig-ove reakcije, iz prekursora 11, uspješno je dobiven spoj 6-fenilamino-2-(4-hidroksifenil)benzotiazol 15, dok sinteza spojeva 16 i 17 nije bila uspješna. Strukture svih sintetiziranih spojeva potvrđene su 1H i 13C NMR spektroskopijom.

Abstract (english)

The aim of this study was the synthesis of novel 2-amino-substituted benzothiazoles 5-7 and 6-amino-substituted benzothiazoles 13-17. For the synthesis of target compounds classical methods of organic synthesis were used. Synthesis of 2-amino-substituted benzothiazole derivatives was carried out by reductive amination to give N-4-(2-phenyl-2-oxoethoxy)benzyl)benzothiazole-2-amine 5, while the synthesis of 6-amino-substituted derivatives was carried out by two syntetic pathways, by nucleophilic substitution reaction and Buchwald-Hartwig reaction. The first synthetic route, by nucleophilic substitution from chlorinated derivative 12, did not yield the target compounds 13 and 14. Compound 6-phenylamino-2-(4-hydroxyphenyl)benzothiazole 15 was successfully synthesized by Buchwald-Hartwig reaction, from precursor 11 while the synthesis of compounds 16 and 17 was not successful. The structures of all the synthesized compounds were confirmed by 1H and 13C NMR spectroscopy.

• Keywords: benzotiazol; amino-supstituirani benzotiazoli; organska sinteza; reduktivno aminiranje; nukleofilna supstitucija; Buchwald-Hartwig-ova reakcija; 1H NMR spektroskopija; 1C NMR spektroskopija
• Keywords (english): benzothiazole; amino-substituted benzothiazoles; organic synthesis; reductive amination; nucleophilic substitution; Buchwald-Hartwig reaction; 1H NMR spectroscopy; 1C NMR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:644027
• 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: Access restricted to students and staff of home institution
• Created on: 2023-05-26 08:44:16