Sinteza i strukturna karakterizacija novih konjugata N-supstituiranih benzimidazola

undergraduate thesis

• Title (english): Synthesis and structural characterization of novel conjugates of N-substituted benzimidazoles
• Author: Viktoria Ravlić
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Ida Boček Pavlinac (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog rada provedena je sinteza i strukturna karakterizacija novih konjugata N-supstituiranih benzimidazola. Ciljani amidino supstituirani benzamidi priređeni su uobičajenim metodama organske sinteze i mikrovalovima potpomognutom sintezom. U prvom sintetskom koraku 4-N supstituirani 3-nitrobenzonitrili 2 i 3 priređeni su mikrovalovima potpomognutom aminacijom 4-klor-3-nitrobenzonitrila 1 uz korištenje odgovarajućeg amina. U drugom koraku spojevi 2 i 3 reducirani su u diamino supstituirane benzonitrile 4 i 5 korištenjem SnCl2 x 2H2O. 2-aminobenzimidazoli 6 i 7 priređeni su ciklokondenzacijom spojeva 4 i 5 korištenjem BrCN-a. U zadnjem koraku sinteze priređeni su 2-benzimidazolil supstituirani benzamidi 10, 11 i 12 kondenzacijom spojeva 6 i 7 s odgovarajućim karboksilnim kiselinama 8 i 9. Ciljani amidino supstituirani spojevi 13 i 14 sintetizirani su Pinnerovom reakcijom u kiselom mediju iz odgovarajućeg cijano supstituiranog spoja 10. Strukture priređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom, a tijek Pinnerove reakcije praćen je IR spektroskopijom.

Abstract (english)

This work presents the synthesis and structural characterization of novel conjugates of N-substituted benzimidazoles. Targeted amidino substituted benzamides were prepared by usual methods of organic chemistry and by microwave-assisted reactions. In first step of synthesis, 4-N substituted 3-nitrobenzonitriles 2 and 3 were prepared by microwave-assisted amination of 4-chloro-3-nitrobenzonitrile 1 using the corresponding amines. In second step, compounds 2 and 3 were reduced to diamino-substituted benzonitriles 4 and 5 using
SnCl2 x 2H2O. 2-aminobenzimidazoles 6 and 7 were prepared by cyclocondensation of compounds 4 and 5 with BrCN. In the last step of synthesis, 2-benzimidazolyl-substituted benzamides 10, 11, and 12 were prepared by condensation of compounds 6 and 7 with the corresponding carboxylic acids 8 and 9. Targeted amidino substituted compounds 13 and 14 were synthesized by Pinner reaction in acidic medium from corresponding cyano substituted 10. Structures of prepared compounds were confirmed with 1H i 13C NMR spectroscopy, while Pinner recation was monitored by IR spectroscopy.

• Keywords: amidi; amidini; benzimidazoli; 1H i 13C NMR spektroskopija; IR spektroskopija; mikrovalna sinteza
• Keywords (english): amides; amidines; benzimidazoles; 1H and 13C NMR spectroscopy; IR spectroscopy; microwave assisted synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:149:594711
• 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
• 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; Embargo expiration date: 2024-06-01
• Created on: 2023-09-26 14:24:40