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undergraduate thesis
Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2019. urn:nbn:hr:149:100722
Vugrin, Leonarda
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

Cite this document

Vugrin, L. (2019). Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:100722

Vugrin, Leonarda. "Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2019. https://urn.nsk.hr/urn:nbn:hr:149:100722

Vugrin, Leonarda. "Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2019. https://urn.nsk.hr/urn:nbn:hr:149:100722

Vugrin, L. (2019). 'Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:100722

Vugrin L. Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2019 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:100722

L. Vugrin, "Sinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2019. Available at: https://urn.nsk.hr/urn:nbn:hr:149:100722

Metadata
TitleSinteza i spektroskopska karakterizacija akrilonitrilnih derivata imidazo[4,5-b]piridina
Title (english)Synthesis and spectroscopic characterization of imidazo[4,5-b]pyridine acrylonitriles
AuthorLeonarda Vugrin
MentorMarijana Hranjec (mentor)
Committee memberMarijana Hranjec (predsjednik povjerenstva)
Committee memberDragana Vuk (član povjerenstva)
Committee memberLidija Furač (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2019-07-12, 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
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:100722
ProjectNumber: 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 programmeTitle: 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 resourceText
File originBorn digital
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Created on2023-05-29 11:55:46