Priprava novih derivata 2-aminobenzimidazola kao potencijalnih biološki aktivnih spojeva

undergraduate thesis

• Title (english): Synthesis of novel 2-aminobenzimidazole derivatives as potential biologically active compounds
• Author: Donata Jambriško
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Maja Cindrić (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-05, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U okviru ovog rada provedena je sinteza novih metoksi derivata Nmetilbenzimidazolil supstituiranih benzamida 17-19 i njihovih cijano derivata 20-22. Ciljani spojevi priređeni su klasičnim reakcijama organske sinteze. Sinteza prekursora 2-amino-5-cijano-1-metilbenzimidazola 10 potpomognuta je mikrovalovima polazeći od 4-klor-3-nitrobenzonitrila 7. Kondenzacijom odgovarajućih supstituiranih benzoil-klorida 14, 15 i 16 s odgovarajućim 2-amino-N-metilbenzimidazolom 6, odnosno 10 priređeni su metoksi supstituirani benzamidi 19-22. Strukture priređenih trimetoksiderivata 19 i 22 potvrđene su 1H NMR i 13C NMR spektroskopijom. Nastanak metoksi 17, 20 i dimetoksi 18, 21 derivata potvrđen je masenom spektrometrijom, no izoliranje istih nije bilo uspješno.

Abstract (english)

In this work, the synthesis of novel methoxy N-methylbenzimidazolyl substituted benzamides 17-19 and their cyano derivatives 20-22 has been carried out. Targeted compounds were prepared by classic organic synthesis reactions. Synthesis of the main precursor, namely 2-amino-5-cyano-1-methylbenzimidazole 10 was endorsed by microwaves starting from 4-chloro-3-nitrobenzonitrile 7. The condensation of the corresponding substituted benzoyl-chlorides 14, 15 and 16 with 2-amino-N-methylbenzimidazole 6 or 2- amino-5-cyano-1-methylbenzimidazole 10 gave methoxy-substituted benzamides 19-22. The structures of the trimethoxy substituted derivatives 19 and 22 were confirmed by means of 1H NMR and 13C NMR spectroscopy. Despite the emergence of methoxy 17, 20 and dimethoxy 18, 21 derivatives was confirmed by mass spectrometry, the isolation of listed compounds has not been successful.

• Keywords: benzamidi; benzimidazoli; organska sinteza; 1H NMR i 13C NMR spektroskopija; masena spektrometrija
• Keywords (english): benzamides; benzimidazoles; organic synthesis; 1H NMR and13C NMR spectroscopy; mass spectrometry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:299707
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-06-24 10:30:03