Sinteza i spektroskopska karakterizacija novih derivata imidazo[4,5-b]piridina

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of novel imidazo[4,5-b]pyridine derivates
• Author: Mirna Dragić
• Mentor: Marijana Hranjec (mentor)
• Mentor: Kristina Starčević (komentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Kristina Starčević (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-07-10, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i spektroskopska karakterizacija novih akrilonitrilnih derivata imidazo[4,5-b]pridina. Aktivnost ovih spojeva značajno ovisi o funkcionalnim skupinama i supstituentima koji su vezani na heterocikličkoj jezgri. Za pripravu ciljanih molekula korištene su klasične metode organske kemije uz sintezu potpomognutu mikrovalnim zračenjem. U prvom stupnju sinteze, za sintezu N-izobutil-3-nitropiridin-2-amina 3, provedena je nukleofilna supstitucija potpomognuta mikrovalovima. Redukcijom N-izobutil-3-nitropiridin-2-amina uz prisutnost katalizatora, priređen je N-izobutilpiridin-2,3-diamin 4.
Glavni prekursor 2-(3-izobutil-3H-imidazo[4,5-b]piridin-2-il)acetonitril 5 priređen je ciklokondenzacijom iz N-izobutilpiridin-2,3-diamina i estera pri čemu dolazi do ciklizacije u imidazo[4,5-b]piridinski prsten. Iz glavnog prekursora, aldolnom kondenzacijom iz aldehida u apsolutnom etanolu, priređeni su E i Z izomeri akrilonitrilnih derivata 12-17. Strukture priređenih spojeva potvrđene su 1H NMR i 13C NMR spektroskopijom. Dodatno je ispitana i antioksidativna aktivnost spojeva 14-17.

Abstract (english)

Within this work, the synthesis and spectroscopic charachterization of novel acrylonitrile imidazo[4,5-b]pyridne derivates was presented. The activity of these compounds significantly depends on the functional groups and substituents attached to the heterocyclic nucleus. For synthesis of novel targeted compounds, classical organic synthesis reactions as well as microwave assistes synthesis were used. In the first step of the synthesis, for the preparation of N-isobutyl-3-nitropyridin-2-amine 3, a microwave assisted nucleophilic substitution was performed. N-isobutylpyridine-2,3-diamine 4 was prepared by reduction
of N-isobutyl-3-nitropyridin-2-amine in the presence of a catalyst. The main precursor
2-(3-isobutyl-3H-imidazo[4,5-b] pyridin-2-yl)acetonitrile 5 was prepared by cyclocondensation from N-isobutylpyridine-2,3-diamine and ester which cyclized to imidazo[4,5-b]pyridine ring. Isomers of acrylonitrile derivatives 12-17 were prepared from the main precursor by aldol condensation from aldehyde in absolute ethanol. The structures of the prepared compounds were confirmed by means of 1H NMR and 13C NMR spectroscopy. Additionally, the antioxidant activity of the compounds 14-17 was tested.

• Keywords: imidazo[4 5-b]piridini; MW 1H i 13C NMR spektroskopija; redukcija; ciklokondenzacija; izomeri
• Keywords (english): imidazo[4 5-b]pyridines; MW 1H and 13C NMR spectroscopy; reduction; cyclocondesation; isomers
• Language: croatian
• URN:NBN: urn:nbn:hr:149:451594
• 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 - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) 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: 2023-05-03 11:56:59