prikaz prve stranice dokumenta Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena
Access restricted to students and staff of home institution
undergraduate thesis
Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. urn:nbn:hr:149:273500
Sačer, Leon
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

Sačer, L. (2021). Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:273500

Sačer, Leon. "Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:273500

Sačer, Leon. "Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:273500

Sačer, L. (2021). 'Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 27 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:273500

Sačer L. Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2021 [cited 2024 December 27] Available at: https://urn.nsk.hr/urn:nbn:hr:149:273500

L. Sačer, "Primjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:149:273500

Metadata
TitlePrimjena zelenih eutektičkih otapala u sintezi novih N-heterocikličkih derivata 1,1'-disupstituiranih ferocena
Title (english)Application of deep eutectic solvents in the synthesis of new N-heterocycle 1,1'-disubstituted ferrocene conjugates
AuthorLeon Sačer
MentorSilvana Raić-Malić (mentor)
Committee memberSilvana Raić-Malić (predsjednik povjerenstva)
Committee memberAndrijana Meščić Macan (član povjerenstva)
Committee memberDanijela Ašperger (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2021-09-15, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Proteklih godina, sve se više koriste načela „zelene“ kemije u sintezi novih biološki aktivnih spojeva. Značajnu važnost u zelenoj kemiji imaju zelena eutektička otapala te mehanokemijska sinteza jer smanjuju uporabu toksičnih hlapljivih organskih otapala. U ovom radu opisana je sinteza novih 1,1'-disupstituiranih ferocenskih derivata purina, purinskih bioizostera i 5-supstituiranih pirimidina (13−23), kao spojeva s potencijalnim antitumorskim djelovanjem. U tu svrhu pripravljen je 1,1'-bis(azidometil)ferocen (1) iz 1,1'-ferocendimetanola. Nadalje, pripravljeni su N-propargilirani derivati purina i purinskih bioizostera (2−8) te 5-supstituiranih pirimidina (9−12). Reakcijom 1,3-dipolarne cikloadicije 1,1'-bis(azidometil)ferocena i odgovarajućih terminalnih alkina (2−12) dobiveno je jedanaest različitih ferocenskih derivata purina, indola, 7-deazapurina (13−19) i pirimidina (20−23). Reakcija 1,3-dipolarne cikloadicije katalizirane bakrom provedena je na četiri različita načina: (i) u metanolu uz bakrov (II) acetat kao katalizator, (ii) u zelenim eutektičkim otapalima D-sorbitol/urea/NH4Cl, (iii) u kolin-klorid/glicerolu uz bakrov (I) jodid kao katalizator i (iv) mehanokemijski uz bakrov (II) acetat kao katalizator. Kao najefikasnija metoda provođenja reakcije 1,3-dipolarne cikloadicije za navedene spojeve pokazala se mehanokemijska sinteza. Strukture spojeva potvrđene su 1H i 13C NMR spektroskopijom, a biološka ispitivanja novosintetiziranih spojeva (13−23) su u tijeku.
Abstract (english)
In recent years, the principles of ˝green˝ chemistry have been more frequently used in the synthesis of new biologically active compounds. Deep eutectic solvents and mechanochemical synthesis are of significant importance in green chemistry because they decrease the use of toxic volatile organic solvents. The aim of this work was the synthesis of 1,1'-disubstituted ferrocene derivatives of purines, purine bioisosteres and 5-substituted pyrimidines, as compounds with potential antitumor activity. For this purpose, 1,1'-bis(azidomethyl)ferrocene (1) was prepared from 1,1'-ferrocendimethanol. Furthermore, propargylated derivatives of purines and purine bioisosteres (2−8) as well as 5-substituted pyrimidines (9−12) were prepared. Eleven ferrocene derivatives of purine, indole, 7-deazapurine (13−19) and 5-substituted pyrimidine (20−23) were obtained by the reaction of 1,3-dipolar cycloaddition of 1,1'-bis(azidomethyl)ferrocene and the corresponding terminal alkynes (2−12). The copper-catalyzed 1,3-dipolar cycloaddition reaction was performed in four different procedures: (i) in methanol with copper (II) acetate as a catalyst, (ii) in green eutectic solvents D-sorbitol/urea/NH4Cl and (iii) in choline chloride/glycerol with copper (I) iodide as a catalyst and (iv) mechanochemically with copper (II) acetate as a catalyst. Mechanochemical synthesis has been shown to be the most effective method for the 1,3-dipolar cycloaddition reaction of these compounds. The structures of the compounds were confirmed by 1H and 13C NMR spectroscopy, and biological studies of compounds (13−23) are ongoing.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:273500
ProjectNumber: IP-2018-01-4682
Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja
Acronym: PurBioCaPa
Leader: Silvana Raić-Malić
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Applied Chemistry - Undergraduate 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: 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 conditionsAccess restricted to students and staff of home institution
Terms of useLicence In copyright icon
Created on2023-04-20 11:16:44