Novi hibridi benzazola i benzena premošteni akrilonitrilom: sinteza Pd-kataliziranim reakcijama i spektroskopska karakterizacija

master's thesis

• Title (english): Novel acrylonitrile bridged hybrids of benzoazoles and benzene: synthesis by Pd-catalysed reaction and spectroscopic characterization
• Author: Petra Koprivnjak
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Committee member: Nataša Perin (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-28, 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: benzaldehid; benzimidazol; akrilonitril; Sonogashira-ina reakcija; Stille-ova reakcija
• Keywords (english): benzaldehyde; benzimidazole; acrylonitrile; Sonogashira reaction; Stille reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:845254
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-11-02 12:26:24