Sinteza i strukturna karakterizacija novih amino supstituiranih pentacikličkih derivata benzimidazola

master's thesis

• Title (english): Synthesis and structural characterization of novel amino substituted pentacyclic benzimidazole derivatives
• Author: Kristina Bobanović
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Tatjana Gazivoda Kraljević (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2015-07-10, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Applied Chemistry

Abstract

U okviru ovog rada provedena je sinteza i spektroskopska karakterizacija novih amino i diamino 6-N-supstituiranih, 3,6-N,N-disupstituiranih i 3-N-supstituiranih derivata 7-cijanobenzo[b]tieno[2,3-b]pirido[1,2-a]benzimidazola. Novi spojevi priređeni su klasičnim reakcijama organske sinteze i reakcijama potpomognutim mikrovalnim zračenjem.
Aciklički derivati benzimidazola 5, 16 i 26 priređeni su reakcijom kondenzacije odgovarajućih halogeno supstituiranih benzo[b]tiofen-2-karbaldehida 4, 15, 25 i 2-cijanometilbenzimidazola 3. Halogeno i dihalogeno supstituirani derivati 7-cijanobenzo[b]tieno[2,3-b]pirido[1,2-a]benzimidazola 7, 18 i 27, kao glavni prekursori za sintezu ciljanih produkata, priređeni su termičkom ciklizacijom spojeva 5, 16 i 26.
Konačni produkti 6-amino supstituirani 8–11, 3,6-diamino supstituirani 19–22 i 3-amino supstituirani derivati 7-cijanobenzo[b]tieno[2,3-b]pirido[1,2-a]benzimidazola 28–31 priređeni su nekataliziranom aminacijom potpomognutom mikrovalnim zračenjem iz prekursora 7, 18 i 27 s odgovarajućim aminima. Strukture priređenih spojeva potvrđene su 1H i 13C NMR i UV/Vis i fluorimetrijskom spektroskopijom te HPLC/MS spektrometrijom.
Priređenim derivatima dodatno su ispitane su spektroskopske karakteristike korištenjem UV/Vis i fluorimetrijske spektroskopije. Kako bi se ispitala mogućnost primjene spojeva 10, 21 i 30 kao optičkih pH senzora, ispitana je i promjena njihovih spektroskopskih svojstava ovisno o vrijednosti pH otopine korištenjem UV/Vis i fluorimetrijske spektroskopije.

Abstract (english)

This work presents the synthesis and spectroscopic characterization of novel amino and diamino 6-N-substitued, 3,6-N,N-disubstitued and 3-N-substitued 7-cyanobenzo[b]thieno[2,3-b]pyrido[1,2-a]benzimidazole derivatives. Novel compounds were prepared by classical reactions of organic chemistry and by microwave assisted reactions.
Acyclic benzimidazole derivatives 5, 16 and 26 were prepared in the reaction of condensation of corresponding benzo[b]thiophenil-2-carbaldehydes 4, 15, 25 and 2-cyanomethylbenzimidazole 3. Halogeno and dihalogeno substitued 7-cyanobenzo[b]thieno[2,3-b]pyrido[1,2-a]benzimidazole derivative 7, as the main precursor for the synthesis of targeted products, were prepared by thermic cyclization of compounds 5, 16 i 26.
Novel 6-amino substitued derivatives 8–11, 3,6-diamino disubstitued 19–21 and 3-amino substitued 7-cyanobenzo[b]thieno[2,3-b]pyrido[1,2-a]benzimidazole derivatives 28–31 were prepared by microwave assisted amination from precursors 7, 18 and 27 with corresponding amines. The structures of all preapred compounds were determined by means of 1H and 13C NMR and UV/Vis and fluorimetric spectroscopy and HPLC/MS spectrometry.
In addition, the spectroscopic properties of prepared compounds were studied by UV/Vis and fluorescence spectroscopy. In order to determine the possibility of compounds 10, 21 and 30 for analytical applications as pH sensors, the changes of their spectroscopic properties depending on the pH value were studied by UV/Vis and fluorescence spectroscopy.

• Keywords: amino supstituirani 7-cijanobenzo[b]tieno[2; 3-b]pirido[1; 2-a]benzimidazoli; 1H i 13C NMR UV/Vis i fluorimetrijska spektroskopija
• Keywords (english): amino substitued 7-cyanobenzo[b]thieno[2; 3-b]pyrido[1; 2-a]benzimidazole derivatives; 1H and 13C NMR UV/Vis and fluorimetric spectroscopy and HPLC/MS spectrometry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:529687
• Study programme: Title: Applied Chemistry - Graduate 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: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2016-12-08 13:09:35