Priprava 1,2,3-triazolnih derivata piran-4-ona iz meta i para-nitrofenilazida i njihov biološki učinak

master's thesis

• Title (english): Synthesis of 1,2,3-triazole derivatives of pyran-4-ones from meta and para-nitrophenyl azides and their biological activity
• Author: Luka Ozdanovac
• Mentor: Vesna Petrović Peroković (mentor)
• Committee member: Vesna Petrović Peroković (predsjednik povjerenstva)
• Committee member: Željka Soldin (član povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Ivan Kodrin (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2018-11-23, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom diplomskom radu opisane su sinteze 1,2,3-triazolnih derivata odabranih
hidroksipiran-4-ona, maltola i kojične kiseline. Triazolni prsten dobiven je klik-reakcijom
terminalnog alkina i azida, poznatom Huisgenovom 1,3-dipolarnom cikloadicijom.
Terminalni alkini 2 i 3 pripravljeni su propargiliranjem maltola i kojične kiseline dok su
aromatski azidi 4 i 5 dobiveni iz para- i meta-nitroanilina. Klik-reakcijom uz bakrov(II) acetat
monohidrat kao katalizator iz terminalnih alkina 2 i 3 i azida 4 i 5 regioselektivno su
sintetizirani 1,4-disupstituirani 1,2,3-triazoli 6-9. Nitro-skupina triazolnih derivata 6-9
reducirana je uz Raney-nikal i hidrazin hidrat u amino-skupinu dajući analogne amino-triazole
10-13. Spojevima 6-13 ispitan je in vitro antibakterijski i antitumorski učinak.
Strukture svih pripravljenih spojeva povrđene su spektroskopijom NMR (1H i DEPTQ) te
spektrometrijom masa (MS).

Abstract (english)

In this diploma thesis the syntheses of 1,2,3-triazole derivatives of selected hydroxypyran-4-
ones, namely maltol and kojic acid, were described. Triazole ring was obtained by click
reaction of terminal alkyne and azide, a well known Huisgen 1,3-dipolar cycloaddition.
Terminal alkynes 2 and 3 were prepared by propargylation of maltol and kojic acid. Aromatic
azides 4 and 5 were synthesized from corresponding para and meta nitroanilines. From
alkynes 2 and 3 as well as azides 4 and 5 1,4-disubstituted 1,2,3-triazoles 6-9 were obtained
next in a regioselective manner using click reaction with copper(II) acetate monohydrate as
catalyst. Nitro group of derivatives 6-9 was reduced to amino group using Raney nickel and
hydrazine hydrate. Thus, analogous amino triazoles 10-13 were prepared. Compounds 6-13
were investigated for their in vitro antibacterial and antitumor effects.
The structures of all prepared compounds were determined by NMR spectroscopy (1H and
DEPTQ) and mass spectrometry (MS).

• Keywords: Huisgenova 1; 3-dipolarna cikloadicija; kojična kiselina; maltol; para-nitrofenilazid; meta-nitrofenilazid; triazoli
• Keywords (english): Huisgen 1; 3-dipolar cycloaddition; kojic acid; maltol; para-nitrophenylazide; meta-nitrophenylazide; triazoles
• Language: croatian
• URN:NBN: urn:nbn:hr:217:632691
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2020-11-23
• Created on: 2018-11-27 10:14:12