Praćenje udjela produkata u reakciji N-ferocenoiliranja C-5 derivata uracila uporabom ¹H-NMR spektroskopije

undergraduate thesis

• Title (english): Monitoring the product content in N-ferrocenoylation reaction of C-5 uracil derivatives using ¹H-NMR spectroscopy
• Author: Ana Kozarac
• Mentor: Jasmina Lapić (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2021-09-08, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

Nukleozidi i njihovi analozi imaju značajnu ulogu u otkrivanju i razvoju lijekova zbog svojih izuzetnih kemoterapijskih aktivnosti, stoga je sintetizirano niz strukturno različitih nukleozida. Prisutnost više nukleofilnih mjesta u nukleobazama sa sličnom reaktivnošću u reakciji N-alkiliranja i N-aciliranja daje smjesu produkata s niskom regioselektivnošću. Slijedom toga u okviru ovog završnog rada praćena je regioselektivnost N-ferocenoiliranja C-5 derivata uracila uporabom ¹H-NMR spektroskopije. Aciliranje baze provodi se ferocenoil kloridom u acetonitrilu uz deprotonirajući reagens trietilamin, pri čemu kao produkt nastaje smjesa N1- i N1/N3-izomera čiji udio ovisi o samom supstituentu na uracilu.

Abstract (english)

Nucleosides and their analogues play a significant role in drug discovery and development due to their exceptional chemotherapeutic activities, therefore a number of structurally different nucleosides have been synthesized. The presence of multiple nucleophilic sites in nucleobases with similar reactivity in the N-alkylation and N-acylation reaction gives a mixture of products with low regioselectivity. In this thesis the regioselectivity of N-ferrocenoylation of C-5 uracil derivatives was monitored using ¹H-NMR spectroscopy. The acylation of the base is carried out with ferrocenoyl chloride in acetonitrile with the deprotonating reagent triethylamine, and the product is a mixture of N1- and N1/N3-isomers, the proportion of which depends on the substituent on uracil.

• Keywords: C-5 derivati uracila; ferocen; ¹H-NMR spektroskopija; pirimidin; regioselektivnost
• Keywords (english): C-5 uracil derivatives; ferrocene; ¹H-NMR spectroscopy; pyrimidine; regioselectivity
• Language: croatian
• URN:NBN: urn:nbn:hr:159:409240
• Study programme: Title: Food Technology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-09-27 09:19:46