Priprava N-substituiranih 2-fenilimidazolov

Cizerle, Patricija (avtor), Požgan, Franc (mentor)

V diplomski nalogi sem raziskovala sintezne pristope za pripravo N-substituiranih 2-fenilimidazolov. Prav tako sem podala primere sintez derivatov imidazola. Preučila sem reakcijske pogoje, ki omogočajo uspešno uvajanje substituentov na dušikov atom v imidazolu. S pomočjo baze, kot sta na primer NaOH ali KOH, sem izvajala deprotonacijo na dušikovem atomu v 2-fenilimidazolu. Zatem pa na to mesto uvajala različne skupine. Na dušikov atom sem uvedla benzilno, butilno, metilno in etilno skupino. Spojine, ki sem jih uporabila, pa so bile benzil bromid, 1-bromobutan, metil jodid in 1,2-dikloroetan. Z uporabo različnih sinteznih pristopov sem pridobila različne produkte, ki sem jih očistila in s spektroskopskimi metodami (1H NMR, IR, HRMS) določila njihove strukture. Spoznala sem, da višja temperatura poveča hitrost kemijske reakcije. Pri vseh primerih pa nisem prišla do pozitivnega rezultata, kar pomeni, da nisem sintetizirala želenega produkta.

• Jezik: Slovenski jezik
• Ključne besede: imidazol, elektrofilna substitucija, deprotonacija, sinteza, 2-fenilimidazol
• Vrsta gradiva: Diplomsko delo/naloga
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2024
• PID: 20.500.12556/RUL-158788
• Datum objave v RUL: 20.06.2024

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Preparation of N-substituted 2-phenylimidazoles

Izvleček

In my thesis, I explored synthetic approaches for the preparation of N-substituted 2-phenylimidazoles. Additionally, I provided examples of the synthesis of imidazole derivatives. I examined the reaction conditions that allow for the successful introduction of substituents on the nitrogen atom in imidazole. Using bases such as NaOH or KOH, I carried out deprotonation on the nitrogen atom in 2-phenylimidazole and subsequently introduced various groups at this position. I introduced benzyl, butyl, methyl, and ethyl groups on the nitrogen atom. The compounds I used were benzyl bromide, 1-bromobutane, methyl iodide, and 1,2-dichloroethane. By employing different synthetic approaches, I obtained various products, which I purified and determined their structures using spectroscopic methods (1H NMR, IR, HRMS). I discovered that higher temperatures increase the rate of the chemical reaction. However, in all cases, I did not achieve a positive result, meaning I did not synthesize the desired product.

• Ključne besede: imidazole, electrophilic substitution, deprotonation, synthesis, 2-phenylimidazole