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master's thesis
Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. urn:nbn:hr:149:285260
Kurajica, Livia
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Kurajica, L. (2017). Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:285260

Kurajica, Livia. "Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:285260

Kurajica, Livia. "Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2017. https://urn.nsk.hr/urn:nbn:hr:149:285260

Kurajica, L. (2017). 'Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 22 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:285260

Kurajica L. Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2017 [cited 2024 November 22] Available at: https://urn.nsk.hr/urn:nbn:hr:149:285260

L. Kurajica, "Novi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2017. Available at: https://urn.nsk.hr/urn:nbn:hr:149:285260

Metadata
TitleNovi hibridi nukleobaza i ferocena: sinteza, strukturna karakterizacija i elektrokemija
Title (english)The novel nucleobase-ferrocene hybrids: synthesis, structural characterization and electrochemistry
AuthorLivia Kurajica
MentorTatjana Gazivoda Kraljević (mentor)
Committee memberTatjana Gazivoda Kraljević (predsjednik povjerenstva)
Committee memberSilvana Raić-Malić (član povjerenstva)
Committee memberMarijana Kraljić Roković (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2017-07-10, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U ovom radu opisana je sinteza novih hibrida nukleobaza i ferocena te njihova strukturna karaktrizacija i elektrokemijska ispitivanja. Reakcijom N-alkiliranja uracilnog ili citozinskog prstena sintetizirani su N-1 i/ili N-3 derivati s propargilnim ili butenilnim supstituentima na uracilnom (1, 4, 7, 8 i 19-21) ili citozinskom (15-17) prstenu koji su nadalje uz natrijev azid prevedeni u 4-azidobutenilne derivate 5, 9, 10 i 23. Paladijem kataliziranom Sonogashira-inom reakcijom unakrsnog povezivanja 5-jod-N-1-propargiluracila (1) s etinilferocenom pripravljen je hibrid 5-joduracila i ferocena (2) premošten etinilnom poveznicom u položaju 5 uracila. Hibridi nukleobaza i 4-ferocenil-1,2,3-triazola (3, 6, 11, 12, 14 i 24) pripravljeni su mikrovalovima potpomognutom „klik“ reakcijom 4-azidobutenskih derivata uracila i citozina s etinilferocenom uz Cu katalizator. „Klik“ reakcijom N-propargiliranih derivata nukleobaza (1 i 13) s azidoferocenom uveden je 1,2,3-triazolni prsten u položaj N-1 i N-3 pri čemu su pripravljeni 4-ferocenil–5-joduracil–1,2,3-triazolni hibrid (3) i N-4-benzoilcitozinski hibrid 4-ferocenil-1,2,3-triazola (14). Strukturna karakerizacija hibrida nukleobaza i ferocena provedena je 1H NMR spektroskopijom. Elektrokemijska ispitivanja novosintetiziranih spojeva provedena su cikličkom voltametrijom.
Abstract (english)
This paper describes the synthesis of new nucleobase and ferrocene hybrids and their structural characterization and electrochemistry. N-1 and/or N-3 derivtives with propargyl or butenyl side chain on uracil (1, 4, 7, 8 and 19-21) or cytosine (15-17) ring were synthesized by N-alkylation reaction, which were with sodium azide converted to 4-azidobutenyl derivatives 5, 9, 10 and 23. The palladium catalyzed cross-coupling Sonogashira reaction of 5-iodo-N-1-propargyluracil (1) with ethinylferrocene gave hybrid of 5-iodouracil and ferrocene (2) bridged with the ethynyl linkage at position 5 of uracil. Hybrids of nucleobases and 4-ferrocenyl-1,2,3-triazoles (3, 6, 11, 12, 14 and 24) were prepared by "click" reaction assisted by microwave irradiation of 4-azidobutene derivatives of uracil and cytosine with ethynylferrocene in the presence of Cu catalyst. 1,2,3-triazole ring was introduced in N-1 and N-3 position by "click" reaction of the N-propargylated nucleobase derivatives (1 and 13) with azidoferrocene where 4-ferocenyl-5-ioduracil-1,3,3-triazole hybrid (3) and N-4-benzoylcytosine 4-ferocenyl-1,2,3-triazole hybrid (14) were prepared. Structural characterization of nucleobase and ferrocene hybrides was performed using 1H NMR spectroscopy. Electrochemical evaluation of novel compounds was performed by cyclic voltammetry.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:285260
Study programmeTitle: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2019-10-02 15:41:56