Priprava 1,2-disupstituiranih derivata imidazola i benzimidazola

master's thesis

• Title (english): Synthesis of 1,2-disubstituted derivatives of imidazole and benzimidazole
• Author: Robert Junior Kolman
• Mentor: Ines Primožič (mentor)
• Committee member: Ines Primožič (predsjednik povjerenstva)
• Committee member: Predrag Novak (član povjerenstva)
• Committee member: Morana Dulić (član povjerenstva)
• Committee member: Ivan Kodrin (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2019-11-06, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog rada opisana je priprava N-supstituiranih imidazolskih i benzimidazolskih
derivata, te njihova supstitucija u položaju 2. N-metilimidazol preveden je u više reakcijskih
koraka u N-metilimidazol-2-karbaldehid, koji je zatim reduciran u odgovarajući alkohol.
Nadalje, iz pripravljenog karbaldehida imidazola sintetiziran je amin u reakciji s benzilaminom.
Pripravljen je i N-benzilimidazol, N-metilbenzimidazol i njegov 2-karbaldehid te 2-
hidroksimetilni derivat. Dodatno, opisana je reakcija analogna Čičibabinovoj aminaciji kao
uzrok nastanka nusprodukata u reakciji karboniliranja N-metilbenzimidazola: 1,1'-dimetil-
2,2'-bibenzimidazola i 2-butil-N-metilimidazola. Identifikacija i kontrola čistoće pripravljenih
spojeva provedena je standardnim analitičkim postupcima, koji uključuju IR i NMR (1H i 13C
(DEPT-Q)) spektroskopiju.

Abstract (english)

In the scope of this work the synthesis of N-substituted derivatives of imidazole and
benzimidazole and their substitution at position 2 was described. N-methylimidazole was
transformed by multiple reaction steps into N-methylimidazole-2-carbaldehyde, which was
subsequently reduced to the corresponding alcohol. Furthermore, the obtained carbaldehyde
was used in synthesis of an amino derivative, in reaction with benzyl-amine. Also, synthesis
of N-benzylimidazole, as well as N-methylbenzimidazole, his 2-carboxaldehyde and 2-
hydroxymethyl derivative was carried out. Additionally, reaction analogous to Chichibabin
amination was described as the cause of byproduct formation in N-methylimidazole
carbonylation reaction: 1,1’-dimethyl-2,2’-bibenzimidazole and 2-butyl-Nmethylbenzimidazole.
Identification and purity control was conducted with standard
analytical methods, including IR, NMR (1H and 13C (DEPT-Q)) spectroscopy.

• Keywords: N-alkliliranje; aminacija; benzimidazol; Čičibabin; imidazol; karboniliranje; redukcija
• Keywords (english): N-alkylation; amination; benzimidazole; Chichibabin; carbonylation; imidazole; reduction
• Language: croatian
• URN:NBN: urn:nbn:hr:217:360812
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2019-11-27 11:29:40