prikaz prve stranice dokumenta Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom
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master's thesis
Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2020. urn:nbn:hr:149:442561
Kos, Marija
University of Zagreb
Faculty of Chemical Engineering and Technology

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

Cite this document

Kos, M. (2020). Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:442561

Kos, Marija. "Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2020. https://urn.nsk.hr/urn:nbn:hr:149:442561

Kos, Marija. "Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2020. https://urn.nsk.hr/urn:nbn:hr:149:442561

Kos, M. (2020). 'Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:442561

Kos M. Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2020 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:442561

M. Kos, "Sinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2020. Available at: https://urn.nsk.hr/urn:nbn:hr:149:442561

Metadata
TitleSinteza i spektroskopska karakterizacija novih amino supstituiranih derivata benzimidazo[1,2-a]kinolina katalitičkom aminacijom
Title (english)Synthesis and spectroscopic characterization of novel amino substituted benzimidazo[1,2-a]quinolones by catalytic amination
AuthorMarija Kos
MentorMarijana Hranjec (mentor)
Committee memberMarijana Hranjec (predsjednik povjerenstva)
Committee memberTatjana Gazivoda Kraljević (član povjerenstva)
Committee memberDragana Mutavdžić Pavlović (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2020-09-11, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U okviru ovog rada provedena je sinteza, optimizacija reakcijskih uvjeta te spektroskopska karakterizacija nastalih produkata dobivenih pri pokušaju sinteze novih aminskih derivata benzimidazo[1,2-a]kinolin-6-karbonitrila. Spojevi su priređeni klasičnim reakcijama organske sinteze te mikrovalovima potpomognutom sintezom. U reakcijama katalitičke Buchwald-Hartwigove aminacije korišten je fosfinski ligand treće generacije. Aciklički prekursor 4 priređen je reakcijom kondenzacije acetonitrila 2 i o-klorbenzaldehida 3, a njegovom termičkom ciklizacijom u sulfolanu pri 280 ºC dobiveni su tetraciklički derivati benzimidazo[1,2-a]kinolina 5a i 5b. Regioizomeri 5a i 5b razdvojeni su kolonskom kromatografijom na silikagelu uz diklormetan kao eluens. Buchwald-Hartwigovom reakcijom aminacije regioizomera 5a i 5b s izobutilaminom proveden je pokušaj sinteze ciljanih amino supstituiranih derivata benzoimidazo[1,2-a]kinolina 6a i 6b. Kako bi se optimirali reakcijski uvjeti, promijenjeni su vrijeme reakcije i vrsta baza te je sinteza provedena termički i pomoću mikrovalova, no željeni spojevi nisu uspješno sintetizirani. Strukture svih prekursora potvrđene su 1H i 13C NMR spektroskopijom dok su strukture dobivenih produkata analizirane masenom spektrometrijom te neke dodatno 1H, 13C i 2D NMR spektroskopijom.
Abstract (english)
This work presents the synthesis, optimisation of reaction conditions and spectroscopic characterisation of the resulting products obtained in an attempt to synthesize novel amino substituted benzimidazo[1,2-a]quinoline-6-carbonitrile derivates. All compounds were prepared by conventional reactions of organic chemistry and microwave assisted synthesis. A third generation of phosphine ligand was used in the catalytic Buchwald-Hartwig amination reactions. Acyclic precursor 4 was prepared by the condensation reaction of acetonitrile 2 and o-chlorobenzaldehyde 3. By its thermal cyclization reaction in sulfolane at 280 ºC tetracyclic derivates of benzimidazo[1,2-a]quinolines 5a and 5b were obtained. Regioisomers 5a and 5b were successfully separated by column chromatography on silicagel by using dichloromethane as an eluent. Buchwald-Hartwig amination of regioisomers 5a and 5b with isobutylamine was used in an attempt to prepare targeted amino substituted benzimidazo[1,2-a]quinoline derivates 6a i 6b. In order to optimize the reaction conditions, the reaction time and base were changed. Also the synthesis was carried out thermally and using microwaves, but the desired compounds were not successfully synthesized. The structures of all precursors were confirmed by means of 1H and 13C NMR spectroscopy, while the structures of the obtained products were characterized by mass spectrometry and some additionally by 1H, 13C and 2D NMR spectroscopy.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:442561
ProjectNumber: IP-2018-01-4379
Title: Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa
Acronym: AntioxPot
Leader: Marijana Hranjec
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Applied Chemistry - Graduate 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: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsAccess restricted to students and staff of home institution
Terms of useLicence In copyright icon
Created on2022-03-05 10:00:04