prikaz prve stranice dokumenta Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije
Embargo period 2025-10-01
master's thesis
Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. urn:nbn:hr:149:986071
Prenc, Sara
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

Prenc, S. (2021). Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:986071

Prenc, Sara. "Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:986071

Prenc, Sara. "Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:986071

Prenc, S. (2021). 'Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 08 August 2024, https://urn.nsk.hr/urn:nbn:hr:149:986071

Prenc S. Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2021 [cited 2024 August 08] Available at: https://urn.nsk.hr/urn:nbn:hr:149:986071

S. Prenc, "Sinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:149:986071

Metadata
TitleSinteza novih derivata benzoksazola primjenom koncepta molekulske hibridizacije
Title (english)Synthesis of new benzoxazole derivatives using the concept of molecular hybridization
AuthorSara Prenc
MentorTatjana Gazivoda Kraljević (mentor)
Committee memberTatjana Gazivoda Kraljević (predsjednik povjerenstva)
Committee memberAndrijana Meščić Macan (član povjerenstva)
Committee memberDragana Mutavdžić Pavlović (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
U ovom radu opisana je sinteza novih derivata benzoksazola konceptom molekulske hibridizacije bakrom kataliziranom klik reakcijom u niskotemperaturnom eutektičkom otapalu (DES) te njihova strukturna karakterizacija 1H- i 13C-NMR spektroskopijom. Kondenzacijom odgovarajuće supstituiranih 4-hidroksibenzaldehida i 2-aminofenola sintetizirani su derivati Schiffovih baza 1-6 koji su nadalje ciklizacijom prevedeni u 2-arilbenzoksazole. Mikrovalovima potpomognutom reakcijom propargiliranja 2-arilbenzoksazola 7-12 s propargil-bromidom uz kalijev karbonat kao bazu sintetizirani su O-propargilirani derivati benzoksazola 13-18. Odgovarajući azidi 19-21 za klik reakciju pripravljeni su reakcijom 1-(2-kloretil)pirolidin-, 1-(2-kloretil)piperidin- i 1-(2-kloretil)morfolin-hidroklorida s natrijevim azidom. Reakcijom O-propargiliranih derivata benzoksazola 13-18 s odgovarajućim azidima 19-21 1,3-dipolarnom cikloadicijom kataliziranom bakrovim (I) jodidom u niskotemperaturnom eutektičkom otapalu (DES) kolin klorid (ChCl)/glicerol (1:2) dobiveni su ciljani 1,2,3-triazolni derivati benzoksazola 22-36 u iskorištenjima 21 - 83 %. Klik reakcijama derivata benzoksazola 13 s aromatskim azidima u eutektičkom otapalu ChCl/glicerol (1:2) dobiveni su 1,2,3-triazolni derivati benzoksazola 39 i 40 u dobrim iskorištenjima.
Abstract (english)
This paper describes the synthesis of new benzoxazole derivatives by molecular hybridization via copper catalyzed click reactions in a deep eutectic solvent (DES) and their structural characterization by 1H- and 13C-NMR spectroscopy. Condensation of substituted 4-hydroxybenzaldehydes and 2-aminophenols yielded the corresponding Schiff bases 1-6 which were further converted to the corresponding 2-arylbenzoxazoles 7-12 by cyclization. O-propargylated benzoxazole derivatives 13-18 were synthesized by propargylation of the obtained 2-arylbenzoxazoles with propargyl bromide and potassium carbonate as the base. In a reaction of N-chloroethylpyrrolidine, N-chloroethylpiperidine and N-chloroethylmorpholine hydrochloride with sodium azide, the corresponding azides 19-21 were prepared. Reaction of O-propargylated benzoxazole derivatives with the corresponding azides by 1,3-dipolar copper-catalyzed cycloaddition in ChCl/glycerol (1:2) based DES yielded the target 1,2,3-triazole benzoxazole derivatives 22-36 in yields 21 - 83 %. Click reactions of benzoxazole derivative 13 with aromatic azides carried out in the ChCl/glycerol (1:2) DES yielded 1,2,3-triazole benzoxazole derivatives 39 i 40 in good yields.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:986071
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 - 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 conditionsEmbargoed access
Embargo expiration date: 2025-10-01
Terms of useLicence In copyright icon
Created on2023-04-13 12:12:51