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

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of imidazo[4,5-b]pyridine acrylonitriles
• Author: Leonarda Vugrin
• 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: 2019-07-12, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i spektroskopska karakterizacija akrilonitrilnih i tetracikličkih derivata imidazo[4,5-b]piridina kao potencijalnih antitumorskih agensa. Za pripravu ciljanih spojeva korištene su klasične metode organske sinteze te sinteza potpomognuta mikrovalovima. S ciljem dobivanja što boljeg iskorištenja ciljanih spojeva, za sintezu amino supstituiranih tetracikličkih derivata korištena su dva sintetska puta. Glavni prekursor 2-cijanometilimidazo[4,5-b]piridin 3, priređen je ciklokondenzacijom
6-klor-2,3-diamino-piridina 1 s 2-cijanoacetamidom 2. U sljedećem stupnju sinteze prvog sintetskog puta provedena je kondenzacija derivata 3 s 2-klorbenzaldehidom 4 te je dobiven aciklički prekursor 5. Termičkom ciklizacijom u sulfolanu priređena je smjesa klorom supstituiranih regioizomera cikličkih prekursora 6a i 6b. Amino supstituirani derivati 7 i 8 priređeni su nekataliziranom aminacijom potpomognutom mikrovalovima te su uspješno odvojeni kolonskom kromatografijom. Strukture novopriređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom, kao i MS spektrometrijom. U drugom sintetskom putu, linearnom sintezom proveden je pokušaj priprave amino supstituiranih derivata imidazo-piridina mikrovalnom i termičkom nekataliziranom reakcijom aminacije. Ciljani produkti nisu uspješno izolirani što je potvrđeno masenom (MS) spektrometrijom.

Abstract (english)

This work presents the synthesis and spectroscopic characterization of
imidazo[4,5-b]pyridine acrylonitriles and tetracyclic derivatives as potential antitumor agents. Classical organic synthesis methods as well as microwave assisted synthesis were used for the preparation of targeted compounds. In order to obtain the better yield of the target compounds, two synthetic pathways were used for the synthesis of amino substituted tetracyclic derivatives. The main precursor, 2-cyanomethylimidazo[4,5-b]pyridine 3, was prepared by cyclocondensation of 6-chloro-2,3-diaminopyridine 1 with 2-cyanoacetamide 2. In the next synthetic step of the first synthetic pathway, the derivative 3 was condensed with 2-chlorobenzaldehyde 4 in order to obtain the acyclic precursor 5. Due to the thermal cyclization in sulfolane, a mixture of chloro substituted cyclic regioisomers 6a and 6b was prepared. Amino substitued derivatives 7 and 8 were prepared by uncatalyzed microwave assisted amination and were successfully separated by column chromatography. The structures of newly prepared compounds were confirmed by means of 1H and 13C NMR spectroscopy as well as MS spectrometry. In the second synthetic pathway, linear synthesis was performed to prepare amino substituted imidazo-pyridine derivatives by microwave and thermal uncatalyzed amination. The desired products were not successfully isolated that was confirmed by mass spectrometry (MS).

• Keywords: aminacija; imidazo[4 5-b]piridini; regioizomeri; MW; 1H i 13C NMR spektroskopija; MS spektrometrija
• Keywords (english): amination; imidazo[4 5-b]pyridines; regioisomers; MW; 1H and 13C NMR spectroscopy; MS spectrometry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:100722
• 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: Applied Chemistry - Undergraduate 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: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-05-29 11:55:46