Sinteza i strukturna karakterizacija novih amidina N-supstituiranih derivata benzimidazola

undergraduate thesis

• Title (english): Synthesis and structural characterization of novel N-substituted benzimidazole amidines
• Author: Petra Gorišek
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Petar Kassal (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-19, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza i spektroskopska karakterizacija amidino supstituiranih benzimidazola i amidino supstituiranih benzotiazola hidorklorida. Ciljani spojevi su priređeni klasičnim metodama organske sinteze, Pinnerovom reakcijom te nekataliziranom aminacijom potpomognutom mikrovalnim zračenjem. Iz 4-klor-3-nitrobenzonitrila 1 reakcijom nukleofilne aromatske supstitucije potpomognute mikrovalovima, priređen je 4-N-metilamino-3-nitrobenzonitril 2 koji u prvoj fazi Pinnerove reakcije daje iminoester 3, pa uvođenjem plinovitog NH3 nastaje 4-amidino-N-metil-2-nitroanilin hidroklorid 4 koji se redukcijom prevodi u 4-amidino-N-metil-1,2-fenilendiamin hidroklorid 5. Kondenzacijom benzaldehida 9-14 s 4-amidino-N-metil-1,2-fenilendiamin hidrokloridom 5 nastaju ciljani derivati amidino supstituiranih benzimidazola 15-20, dok derivati benzimidazola 21-23 nastaju kondenzacijom 4-amidino supstituiranih 1,2-fenilendiamina 5-8 s 5-brom-2-hidroksi-benzaldehidom 14. Ciljani derivati amidino supstituiranih benzotiazola hidorklorida 26-27 priređeni su reakcijom iz ranije pripravljenih spojeva 24 i 25 s 5-brom-2-hidroksi-benzaldehidom 14. Struktura svih priređenih spojeva potvrđena je korištenjem 1H i 13C NMR spektroskopije. Ciljani spojevi 20, 27, 28 i 29 okarakterizirani su UV/Vid spektroskopijom u otapalima različite polarnosti. Provedene su UV/Vid titracije otopina spojeva 20, 27, 28 i 29 u puferima različitih pH vrijednosti u svrhu ispitivanja njihove moguće primjene kao senzora.

Abstract (english)

The aim of this study was the synthesis and spectroscopic characterization of amidino substituted benzimidazoles and amidino substituted benzothiazoles hydrochlorides. Targed compounds were prepared by classical reactions of organic chemistry, the Pinner reaction and uncatalyzed microwave assisted amination. From 4-chloro-3-nitrobenzonitrile 1 by microwave assisted reaction of nucleophilic aromatic substitution, 4-N-methylamino-3-nitrobenzonitrile 2 was prepared, which gave in the first stage of the Pinner reaction iminoester 3, and by introducing gaseous NH3 4-amindino-N-methyl-2-nitroaniline hydrochloride 4 is formed, which is transformed into 4-amidino-N-methyl-1,2-phenylendiamine hydrochloride 5 by reduction. Targed derivates of amidino substituted benzimidazoles 15-20 were prepared by condensation from benzaldehydes 9-14 and N-methyl-1,2-phenylendiamine hydrochloride 5, while benzimidazole derivates 21-23 are formed by condensation of 4-amidino-substituted 1,2-phenylendiamines 5-8 with 5-bromo-2-hydroxy-benzaldehyde 14. Targed derivates of amidino substituted benzothiazole hydrochlorides 26-27 were prepared by reaction of previously prepared compounds 24 and 25 with 5-bromo-2-hydroxy-benzaldehyde 14. The structures of all synthesized compounds were confirmed by means of 1H and 13C NMR spectroscopy. Targeted compounds 20, 27, 28 and 29 were characterized by UV/Vis spectroscopy in several organic solvents with different polarities. In order to explore the possible application of compounds 20, 27, 28 and 29 as optical pH sensors, UV/Vis titration of aqueous compounds solution with buffer solution with different pH were performed.

• Keywords: amidini; benzimidazoli; benzotiazoli; NMR i IR spektroskopija; UV/Vid; pH senzori; Pinnerova reakcija
• Keywords (english): amidines; benzimidazoles; benzothiazoles; NMR and IR spectroscopy; UV/Vis; pH sensors; Pinner reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:280779
• Project: Number: 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
• Project: Number: IP-2020-02-8090; Title: Dizajn, sinteza i računalna analiza novih optičkih kemijskih pH osjetilnih derivata benzazola; Title: Design, Synthesis and Computational Analysis of Novel Optical Chemical pH Sensing Benzazole Derivatives; Acronym: BenzpHSens; Leader: Robert Vianello; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Chemical Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2023-02-23 14:03:29