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undergraduate thesis
Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. urn:nbn:hr:149:615371
Piškor, Martina
University of Zagreb
Faculty of Chemical Engineering and Technology

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

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Piškor, M. (2017). Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:615371

Piškor, Martina. "Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:615371

Piškor, Martina. "Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:615371

Piškor, M. (2017). 'Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 03 April 2025, https://urn.nsk.hr/urn:nbn:hr:149:615371

Piškor M. Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2017 [cited 2025 April 03] Available at: https://urn.nsk.hr/urn:nbn:hr:149:615371

M. Piškor, "Sinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2017. Available at: https://urn.nsk.hr/urn:nbn:hr:149:615371

Metadata
TitleSinteza novih 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina
Title (english)Synthesis of novel 4-phenyl-1,2,3-triazolyl derivatives of benzimidazo[1,2-a]quinolines
AuthorMartina Piškor
MentorSilvana Raić-Malić (mentor)
Committee memberSilvana Raić-Malić (predsjednik povjerenstva)
Committee memberTatjana Gazivoda Kraljević (član povjerenstva)
Committee memberDanijela Ašperger (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2017-09-18, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
Cilj ovog rada bila je regioselektivna sinteza 4-fenil-1,2,3-triazolnih derivata benzimidazo[1,2-a]kinolina (3−6, 11, 12) kao spojeva s potencijalnim antitumorskim djelovanjem. U tu svrhu iz 5-klorbenzimidazo[1,2-a]kinolin-6-karbonitrila (1) i njegovih 2-kloriranih i 2-fluoriranih derivata (7, 9) sintetizirani su azidi benzimidazo[1,2-a]kinolin-6-karbonitrila 2, 8 i 10. 1,2,3-triazolni derivati benzimidazo[1,2-a]kinolina 3−6, 11 i 12 pripravljeni su reakcijom 1,3-dipolarne cikoladicije... More odgovarajućeg azida (2, 8, 10) i različitih terminalnih alkina uz Cu(I), kao katalizator, prema načelima ΄klik΄ kemije. Kako bi se dobilo što bolje iskorištenje ciljanih spojeva, kod sinteze spojeva 4, 5 i 6 korištena su dva sintetska puta. Prvi sintetski put uključuje reakciju prevođenja 5-klorbenzimidazo[1,2-a]kinolina-6-karbonitrila (1) u azid 2 i njegovu izolaciju te potom ΄klik΄ reakciju azida 2 i odgovarajućih alkina u 1,4-disupstituirane 1,2,3-triazolne derivate benzimidazo[1,2-a]kinolina (3−6). Drugi sintetski put bila je tandemska reakcija u kojoj se azid 2 nije izolirao nego je in situ reagirao s odgovarajućim terminalnim alkinima pri čemu su dobiveni 1,4-disupstituirani 1,2,3-triazolni derivati benzimidazo[1,2-a]kinolina 4, 5 i 6. Reakcije su provođene pri povišenoj temperaturi, a produkti reakcija su izolirani kolonskom kromatografijom. Strukture svih sintetiziranih spojeva potvrđene su spektroskopijom 1H i 13C NMR. Less
Abstract (english)
The aim of this work was the regioselective synthesis of novel 4-phenyl-1,2,3-triazolyl substituted benzimidazo[1,2-a]quinolines (3−6, 11, 12) with potential antitumor activity. For this purpose, 5-chlorobenzimidazo[1,2-a]quinoline-6-carbonitrile (1) and its 2-chloro and 2-fluoro derivatives (7, 9) were converted to the corresponding azido derivatives of benzimidazo[1,2-a]quinoline 2, 8 and 10. 1,2,3-Triazole derivatives of benzimidazo[1,2-a]quinoline 3−6, 11 and 12 were then prepared... More using 1,3-dipolar cycloaddition reaction of the corresponding azide derivative (2, 8, 10) and corresponding terminal alkynes with Cu(I), as a catalyst, following the concept of ´click´ chemistry. In order to obtain better overall yield of the target compounds, two synthetic pathways were used in the synthesis of compounds 4, 5 and 6. First pathway included the conversion of the 5-chlorobenzimidazo[1,2-a]quinoline-6-carbonitrile (1) to the azide 2, its isolation and then a ´click´ reaction of the azide 2 and the corresponding alkynes to form 1,4-disubstituted 1,2,3-triazole derivatives of benzimidazo[1,2-a]quinoline (3−6). Second synthetic pathway was a tandem reaction in which the azido derivative 2 was not isolated, but in situ reacted with the corresponding terminal alkynes to afford, 1,4-disubstituted 1,2,3-triazole derivatives of benzimidazo[1,2-a]quinoline 4, 5 and 6. The reactions were performed at reflux, and the reaction products were isolated by column chromatography. The structures of all compounds have been confirmed by 1H and 13C NMR spectroscopy. Less
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:615371
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
Access conditionsOpen access
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Created on2021-03-12 12:22:56
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