Sinteza i spektroskopska karakterizacija novih biološki aktivnih amino-supstituiranih pentacikličkih derivata benzimidazola

master's thesis

• Title (english): Synthesis and spectroscopic characterization of novel amino supstituted pentacyclic derivatives of benzimidazoles
• Author: Marjana Gulin
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Maja Cindrić (član povjerenstva)
• Committee member: Šime Ukić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-02-28, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i spektroskopska karakterizacija novih biološki aktivnih amino-supstituiranih pentacikličkih derivata benzimidazola. Novi spojevi su priređeni su klasičnim reakcijama organske sinteze. Fotokemijskom ciklizacijom etanolne otopine acikličkog prekursora E-2-(2-benzimidazolil)-3-(3-kinolinil)akrilonitrila 3 dobiven je ciklički derivat, benzo[g]benzo[4,5]imidazo[1,2-a][1,5]naftiridin-7-karbonitril 4. Ciklički produkt benzo[g]benzo[4,5]imidazo[1,2-a][1,8]naftiridin-6-karbonitril 7 priređen je termičkom ciklizacijom E-2-(2-benzimidazolil)-3-(2-klor-3-kinolinil)akrilonitrila 6 koja je provedena u sulfolanu. Amino supstituirani pentaciklički derivati benzimidazola 11-14 pripravljeni su nekataliziranom reakcijom aminacije potpomognute mikrovalovima cikličkog derivata 11-fluorbenzo[g]benzo[4,5]imidazo[1,2-a][1,8]naftiridin-6-karbonitrila 10. Spojevi 19-21 priređeni su sintezom potpomognutom mikrovalovima iz klorom supstituiranog cikličkog derivata 7-klorbenzo[g]benzo[4,5]imidazo[1,2-a][1,8]naftidrin-6-karbonitril 18 u acetonitrilu i uz suvišak odgovarajućih amina. Strukture novopriređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom a neki spojevi su okarakterizirani UV/Vis i fluorimetrijskom spektroskopijom.

Abstract (english)

This work presents the synthesis and spectroscopic characterization of novel amino supstituted pentacyclic benzimidazole derivatives. Novel compounds were prepared by classical reactions of organic chemistry. Cyclic derivative benzo[g]benzo[4,5]imidazo[1,2-a][1,5]napthyridine-7-carbonitrile 4 was prepared by photochemical cyclization of ethanolic solution of E-2-(2-benzimidazolyl)-3-(3-quinolinol)acrylonitrile 3. Within the reaction of thermal cyclization of E-2-(2-benzimidazolyl)-3-(2-chloro-3-quinolinyl)acrylonitrile 6 in sulfolane cyclic derivative benzo[4,5]imidazo[1,2-a][1,8]napthyridine-6-carbonitrile 7 was prepared. Amino supstituted pentacyclic benzimidazole derivatives 11-14 were prepared by uncatalyzed microwave assisted amination from cyclic derivative 11-fluorobenzo[g]benzo [4,5]imidazo[1,2-a][1,8]naphthyridine-6-carbonitrile 10. Compounds 19-21 were prepared by using microwaves assisted amination from chloro substituted cyclic derivative 7-chlorobenzo[g]benzo[4,5]imidazo[1,2-a][1,8]naftiridin-6-carbonitrile 18 in acetonitrile with corresponding amines. The structures of all newly prepared compounds were confirmed by means of 1H i 13C NMR spectroscopy, while some compounds were also characterized by UV/Vis and fluorimetric spectroscopy.

• Keywords: amini; benzimidazoli; UV/Vis i fluorimetrijska spektroskopija; 1H i 13C NMR spektroskopija
• Keywords (english): amines; benzimidazoles; UV/Vis and fluorimetric spectroscopy; 1H and 13C NMR spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:041497
• 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: Access restricted to students and staff of home institution
• Created on: 2022-02-21 12:40:33