Synthesis of 1,2-disubstituted derivatives of imidazole and benzimidazole

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.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