prikaz prve stranice dokumenta 1,3-dipolarna cikloadicija alkina i azida
  Download
PDF 977.64 KB
undergraduate thesis
1,3-dipolarna cikloadicija alkina i azida
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. urn:nbn:hr:149:284510
Milošević, Josipa
University of Zagreb
Faculty of Chemical Engineering and Technology

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

Cite this document

Milošević, J. (2015). 1,3-dipolarna cikloadicija alkina i azida (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:284510

Milošević, Josipa. "1,3-dipolarna cikloadicija alkina i azida." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:284510

Milošević, Josipa. "1,3-dipolarna cikloadicija alkina i azida." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:284510

Milošević, J. (2015). '1,3-dipolarna cikloadicija alkina i azida', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 26 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:284510

Milošević J. 1,3-dipolarna cikloadicija alkina i azida [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2015 [cited 2024 December 26] Available at: https://urn.nsk.hr/urn:nbn:hr:149:284510

J. Milošević, "1,3-dipolarna cikloadicija alkina i azida", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2015. Available at: https://urn.nsk.hr/urn:nbn:hr:149:284510

Metadata
Title1,3-dipolarna cikloadicija alkina i azida
Title (english)1,3-dipolar cycloaddition of alkynes and azides
AuthorJosipa Milošević
MentorSilvana Raić-Malić (mentor)
Committee memberSilvana Raić-Malić (predsjednik povjerenstva)
Committee memberAndrijana Meščić (član povjerenstva)
Committee memberAnte Jukić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2015-09-18, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
Cilj ovog rada bila je regioselektivna sinteza 1,4-disupstituiranih-1,2,3-triazolnih derivata L-askorbinske kiseline (2–11) kao spojeva s potencijalnim antitumorskim djelovanjem. 1,2,3-triazolni derivati (2–8) pripravljeni su reakcijom 1,3-dipolarne cikoladicije koja se temelji na konceptu “klik” kemije uz Cu(I) kao katalizator. Za sintezu spojeva 2–8 koristila se tandemska reakcija tosiliranog derivata L-askorbinske kiseline (1) i odgovarajućih terminalnih alkina bez izoliranja azidnog derivata L-askorbinske kiseline koji nastaje kao međuprodukt. Sinteze spojeva 2–8 su se provodile primjenom mikrovalova pri temperaturi od 80 °C i 300 W. Kako bi se ispitalo antioksidativno djelovanje 1,2,3-triazolnih derivata L-askorbinske kiseline, priređeni su derivati L-askorbinske kiseline 9−11 sa slobodnim hidroksilnim skupinama uklanjanjem benzilne zaštite. Strukture svih sintetiziranih spojeva (2–11) potvrđene su 1H- i 13C-NMR spektroskopijom.
Abstract (english)
The aim of this work was the synthesis of 1,4-disubstituted 1,2,3-triazole derivatives of L-ascorbic acid (2–11) with potential antiproliferative activity using regioselective approach. 1,2,3-triazole derivatives (2–8) were prepared using 1,3-dipolar cycloaddition reaction based on the concept of "click" chemistry with Cu(I) as a catalyst. For the synthesis of compounds 2–8 tandem reaction of the tosylated L-ascorbic acid derivative (1) and corresponding alkynes was used without the isolation of the C-6 azide L-ascorbic acid derivative. The synthesis of compound 2–8 was conducted using microwave irradiation at 80 °C and 300 W. In order to explore the antioxidant properties of the 1,2,3-triazole L-ascorbic acid derivatives, compounds 9–11 with free hydroxyl groups were prepared by removal of the benzyl protection. The structures of all compounds (2–11) have been confirmed by 1H- and 13C-NMR spectroscopy.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:284510
Study programmeTitle: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Environmental chemistry and green technologies
Study programme type: university
Study level: undergraduate
Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2016-12-02 13:52:00