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master's thesis
Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. urn:nbn:hr:149:845254
Koprivnjak, Petra
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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Koprivnjak, P. (2018). Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:845254

Koprivnjak, Petra. "Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:845254

Koprivnjak, Petra. "Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2018. https://urn.nsk.hr/urn:nbn:hr:149:845254

Koprivnjak, P. (2018). 'Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:845254

Koprivnjak P. Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2018 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:845254

P. Koprivnjak, "Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:149:845254

Metadata
TitleNovi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija
Title (english)Novel acrylonitrile bridged hybrids of benzoazoles and benzene: synthesis by Pd-catalysed reaction and spectroscopic characterization
AuthorPetra Koprivnjak
MentorTatjana Gazivoda Kraljević (mentor)
Committee memberTatjana Gazivoda Kraljević (predsjednik povjerenstva)
Committee memberLidija Furač (član povjerenstva)
Committee memberNataša Perin (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2018-09-28, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U ovom radu je opisana sinteza novih hibrida benzazola i benzena premoštenih akrilonitrilom te njihova strukturna karakterizacija 1H-NMR spektroskopijom. Paladijem kataliziranom Sonogashira-inom reakcijom unakrsnog povezivanja 4-klor- odnosno 4-brombenzaldehida s terminalnim alkinima pripravljeni su 4-alkinilni derivati benzaldehida 1-3, 5 i 7. Stille-ovom reakcijom 4-klor- ili 4-brombenzaldehida s organokositrovim spojevima sintetizirani su spojevi 8 i 9 koji su nadalje reakcijom kondenzacije s 2-cijanometilbenzimidazolom prevedeni u hibride benzimidazola i 4-furil i 4-tienilbenzena premoštene akrilonitrilom 14 i 15. Kondenzacijom priređenih 3-O-propargil-, 3-klormetil- i 3-azidometilbenzaldehida (20, 22 i 24) s 2-cijanometilbenzimidazolom sintetizirani su konjugati s akrilonitrilnom poveznicom 21, 23 i 25. Spektroskopijom 1H-NMR potvrđene su strukture svih novopripravljenih spojeva. Farmakološki učinci i moguće biološke mete sintetiziranih spojeva predviđeni su in silico analizom (PASS).
Abstract (english)
This paper describes the synthesis of novel benzazoles and benzen hybrids bridged with acrylonitrile and their structural characterization by 1H NMR spectroscopy. The palladium-catalyzed cross-coupling Sonogashira reaction of 4-chloro- or 4-bromobenzaldehyde with terminal alkynes, 4-alkinyl derivatives of benzaldehyde 1-3, 5 and 7 were prepared. Stille reaction of 4-chloro- or 4-bromobenzaldehyde coupling with organostannanes gave compounds 8 and 9, which were further converted by condensation reaction with (2-benzimidazolylmethyl)nitrile to hybrids of benzimidazole and 4-furyl i 4-thienylbenzene bridged by acrylonitrile 14 and 15. Condensation reaction of prepared 3-O-propargyl-, 3-chloromethyl- and 3-azidomethylbenzaldehyde (20, 22 and 24) with (2-benzimidazolylmethyl)nitrile gave conjugates with acrylonitrile linker 21, 23 and 25. Structures of novel compounds were confirmed by 1H-NMR spectroscopy. Pharmacological effects and possible biological targets of synthesized compounds are predicted by in silico analysis (PASS).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:845254
Study programmeTitle: Environmental Engineering - Graduate study
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra inženjer/inženjerka ekoinženjerstva (magistar/magistra inženjer/inženjerka ekoinženjerstva)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2020-11-02 12:26:24