Sinteza i strukturna karakterizacija novih aril-supstituiranih derivata imidazo[4,5-b]piridina

master's thesis

• Title (english): Synthesis and structural characterization of novel aryl-substituted imidazo[4,5-b]pyridine derivatives
• Author: Mirna Dragić
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-28, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i strukturna karakterizacija novih arilnih derivata imidazo[4,5-b]piridina. Sinteza ciljanih spojeva provedena je iz odgovarajućih imidazo[4,5-b]piridina Suzuki-Miyaura reakcijama križnog povezivanja, klasičnim zagrijavanjem i zagrijavanjem potpomognutim mikrovalnim zračenjem. Reakcije su optimirane u sustavima otapala korištenjem različitih baza i katalizatora. Prekursor za Suzuki-Miyaura reakciju, spoj 3, priređen je ciklokondenzacijom iz 5-brom-2,3-diaminopiridina i benzaldehida. Iz prekursora 3 i arilnih bornih kiselina, priređeni su spojevi 4-8. Također, provedena je i reakcija zaštite NH skupine u svrhu uspješnije Suzuki-Miyaura reakcije. Iz 4-(2-fenil-3H-imidazo[4,5-b]piridin-6-il)benzonitrila 5, Pinnerovom reakcijom priređen je i amidino supstituirani spoj 6-(4-(4,5-dihidro-1H-imidazol-2-il)fenil)-2-fenil-3H-imidazo[4,5-b]piridin 9. Tijek Pinnerove reakcije praćen je IR spektroskopijom. Strukture svih novosintetiziranih spojeva potvrđene su 1H i 13C NMR spektroskopijom, a nekim je spojevima struktura dodatno okarakterizirana i masenom spektrometrijom.

Abstract (english)

Within this work, the synthesis and structural charachterization of novel aryl-substituted imidazo[4,5-b]pyridne derivates was presented. The synthesis of the target compounds was carried out from the corresponding imidazo[4,5-b]pyridines by Suzuki-Miyaura cross-coupling reactions by classical heating and microwave-assisted heating. Reactions were optimized in solvent systems using different bases and catalysts. Precursor for Suzuki-Miyaura reaction, compound 3, was prepared by cyclocondensation of 5-bromo-2,3-diaminopyridine and benzaldehyde. Compounds 4-8 were prepared from precursor 3 and aryl boronic acids. Also, the protection reaction of the NH group was carried out for the purpose of a more successful Suzuki-Miyaura reactions. The amidino substituted compound 6-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-phenyl-3H-imidazo[4,5-b]pyridine 9, was prepared by the Pinner reaction from 4-(2-phenyl-3H-imidazo[4,5-b]pyridin-6-yl)benzonitrile 5. The Pinner reaction was monitored by IR spectroscopy. The structures of all newly synthesized compounds were confirmed by 1H and 13C NMR spectroscopy, while the structure of some compounds was additionally characterized by mass spectrometry.

• Keywords: imidazo[4 5-b]piridini; MW; 1H i 13C NMR spektroskopija; Suzuki-Miyaura reakcija; Pinnerova reakcija; masena spektrometrija; IR spektroskopija
• Keywords (english): imidazo[4 5-b]pyridines; MW; 1H and 13C NMR spectroscopy; Suzuki-Miyaura reaction; Pinner reaction; mass spectrometry; IR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:759909
• Project: Number: 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 programme: Title: Materials Science and Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka kemijskog inženjerstva (magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-03-28 09:22:16