Synthesis of novel imidazole-2-aldoxime carbamates

U okviru ovog rada opisani su načini priprave novih karbamata oksima 1-benzilimidazol2-karbaldehida polazeći od 1H-imidazola. Sinteza 1-benzilimidazol-2-karbaldehid-oksima provedena je u dva koraka: prvo je benziliran dušikov atom imidazola na položaju jedan, a zatim formiliran ugljikov atom imidazola na položaju dva korištenjem N,Ndimetilformamida i n-butillitija kao baze. Aldehid je zatim preveden u aldoksim reakcijom s hidroksilamonijevim kloridom. Klasičnim reakcijama u otopini pripravljena su četiri karbamata oksima 1-benzilimidazol-2-karbaldehida koji dosad nisu opisani u literaturi. Za njihovu sintezu korišteni su odgovarajući izocijanati (fenil i cikloheksil) te N,Ndisupstituirani karbamoil-kloridi (N,N-dimetil i N,N-difenil). Tijek reakcija praćen je tankoslojnom kromatografijom. Strukture novih spojeva potvrđene su metodama infracrvene spektroskopije te jednodimenzionalne spektroskopije nuklearne magnetske rezonancije (1H i 13C).Synthesis of novel oxime carbamates of 1-benzylimidazole, starting from 1H-imidazole, has been described within this diploma thesis. Synthesis of 1-benzylimidazole-2-carbaldehyde was carried out in two steps: imidazole was first benzylated at the nitrogen atom on position one and then formilation occured on the carbon atom on position two using N,N-dimethylformamide and n-butyllithium as base. Aldehyde was then transformed into an aldoxime by reaction with hydroxylammonium chloride. Using classic reactions in solution, four novel oxime carbamates of 1-benzylimidazole-2-carbaldehyde were synthesised which had not yet been described in literature. Reagents used for their syntheses were isocyanates (phenyl and cyclohexyl) and N,Ndisubstituted carbamoyl chlorides (N,N-dimethyl and N,N-diphenyl). Course of the reactions was monitored by thin-layer chromatography. Chemical structures of novel compounds were confirmed by infrared spectroscopy and one-dimensional nuclear magnetic resonance spectroscopy (1H and 13C)