Sinteza, spektroskopska karakterizacija i biološka aktivnost novih amidnih derivata benzimidazo[1,2-a]kinolina

master's thesis

• Title (english): Synthesis, biological activity and spectroscopic characterization of novel benzimidazo[1,2-a]quinoline carboxamide derivatives
• Author: Jasna Alić
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Irena Sović (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2016-09-29, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U okviru ovog rada provedena je sinteza i spektroskopska karakterizacija novih karboksamido i dikarboksamido 6-N-supstituiranih, 2,6-N,N-disupstituiranih te 2-N-supstituiranih derivata benzimidazo[1,2-a]kinolina. Ciljani spojevi pripravljeni su klasičnim reakcijama organske i fotokemijske sinteze. Aciklički prekursori 3, 16 i 24 pripravljeni su reakcijom kondenzacije odgovarajućih različito supstituiranih benzaldehida 2 i 15 s 2-cijanometil i 2-metil benzimidazolima 1 i 23. Ciklički derivati benzimidazo[1,2-a]kinolina, 4, 17 i 25, priređeni su termičkom ciklizacijom acikličkog prekursora 3 u sulfolanu na 280 °C, te reakcijom fotokemijske dehidrociklizacije spojeva 16 i 24 u etanolu uz dodatak joda i osvjetljavanjem UV-Hg lampom od 400 W. Kiselo kataliziranom hidrolizom cijano supstituiranih derivata 4, 17 i 25 priređene su odgovarajuće karboksilne kiseline 5, 18 i 26 koje su u reakciji s tionil-kloridom dale acilne halogenide 6, 19 i 27. N-karboksamido supstituirani derivati benzimidazo[1,2-a]kinolina 7, 8, 10–14, 20–22 te 28–31 sintetizirani su u reakciji acilnih halogenida benzimidazo[1,2-a]kinolina 6, 19 i 27 s odgovarajućim aminima u suhom diklormetanu. Strukture priređenih produkata potvrđene su 1H i 13C NMR spektroskopijom a spojevi su dodatno okarakterizirani UV/Vis i fluorimetrijskom spektroskopijom. Korištenjem UV/Vis spektroskopije provedena je spektroskopska karakterizacija ciljanih derivata 7, 8, 10–14, 20–22 te 28–31 dok su fluorimetrijska ispitivanja provedena za tri N-piperidinil supstituirana derivata 7, 20 i 28.

Abstract (english)

This work presents the synthesis and spectroscopic characterization of novel carboxamido and dicarboxamido 6- N-substituted, 2,6-N, N-disubstituted and 2-N-substituted benzimidazole[1,2-a]quinoline derivatives. Target compounds were prepared by conventional reactions of organic and photochemical synthesis. Acyclic precursors 3, 16 and 24 were prepared by the condensation reaction of the corresponding variably substituted benzaldehyde 2 and 15 with 2-cyanomethyl, and 2-methyl benzimidazole 1 and 23. The cyclic derivatives of benzimidazole[1,2-a]quinolines, 4, 17 and 25, were prepared by the thermal cyclization of the acyclic precursor 3 in sulfolane at 280 °C, and by reaction of the photochemical dehydrocyclization of compound 16 and 24 in ethanol with added iodine by illuminating with UV-Hg lamp of 400 W. Corresponding carboxylic acids 5, 8 i 26 were prepared by acidic hydrolysis of cyano substituted derivatives 4, 17 i 25. In the reaction of carboxylic acids 5, 8 i 26 with thionyl-chloride corresponding acyl halogenides 6, 19 and 27 were obtained. N-carboxamido substituted benzimidazole[1,2-a]quinoline derivatives, 7, 8, 10–14, 20–22 and 28–31 were synthesized in the reacion of benzimidazole[1,2-a]quinoline acyl halogenides 6, 19 and 27 with corresponding amines in dry dichloromethane. The structures of prepared compounds were confirmed by means of 1H and 13C NMR, and characterized by UV/Vis and fluorimetric spectroscopy. The spectroscopic properties of target derivatives 7, 8, 10–14, 20–22 and 28–31 were studied by UV / Vis spectroscopy while the fluorimetric tests were conducted for the three N-substituted piperidinyl derivatives 7, 20 and 28.

• Keywords: benzimidazoli; karboksamido supstituirani benzimidazo[1 2-a]kinolini; 1H i 13C NMR; UV/Vis i fluorimetrijska spektroskopija
• Keywords (english): benzimidazoles; carboxamido substituted benzimidazole[1 2-a]quinolines; 1H and 13C NMR; UV/Vis and fluorimetric spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:784141
• Study programme: Title: Chemical 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: Open access
• Created on: 2017-11-24 12:27:10