Priprava adamantilnih i manoznih derivata novih N-aril supstituiranih 3-hidroksipiridin-4-ona dobivenih iz kojične kiseline

master's thesis

• Title (english): Synthesis of adamantyl and mannosyl derivatives of novel N-aryl substituted 3-hydroxypyridin-4-ones obtained from kojic acid
• Author: Karlo Meglić
• 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: Ivana Biljan (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2016-12-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U prvom dijelu ovog diplomskog rada opisana je priprava 1-fenil-5-hidroksi-2-
hidroksimetilpiridin-4-ona (1) i 5-hidroksi-2-hidroksimetil-1-(p-metoksifenil)piridin-4-ona (2).
Spojevi 1 i 2 priređeni su izravnim postupkom iz kojične kiseline i anilina ili p-metoksianilina uz
dodatak kiselog katalizatora (p-TsOH) u zatvorenoj staklenoj cijevi. Iz spojeva 1 i 2 Steglichovom
esterifikacijom priređeni su lipofilni piridinonski esteri adamantan-1-iloctene kiseline, spojevi 3 i
4.
U drugom dijelu rada opisana je priprava novih N-aril-3-hidroksipiridin-4-onskih derivata,
1-fenil-3-hidroksipiridin-4-ona (8) i 3-hidroksi-1-(p-metoksifenil)piridin-4-ona (9). Spojevi 8 i 9
pripravljeni su iz prethodno sintetski modificirane kojične kiseline (6 i 7) i odabranih arilamina,
anilina i p-metoksianilina. Iz spojeva 8 i 9 Koenigs-Knorrovom metodom pripravljeni su najprije
acetilirani manozni derivati 10 i 11, a zatim Zemplénovim postupkom deacetilirani piridinonski
manozidi 12 i 13.
Strukture svih priređenih spojeva određene su NMR spektroskopijom (1H i 13C) i
spektrometrijom masa (MS).

Abstract (english)

In the first part of this diploma thesis the preparation of 5-hydroxy-2-hydroxymethyl-1-
phenylpyridin-4-one (1) and 5-hydroxy-2-hydroxymethyl-1-(p-methoxyphenyl)pyridin-4-one (2)
is described. Compounds 1 and 2 were prepared by direct approach from kojic acid and aniline or
p-methoxyaniline with the addition of acid catalyst (p-TsOH) in a sealed glass vessel. Lipophilic
pyridinone esters of adamantan-1-ylacetic acid, 3 and 4, were obtained next by Steglich
esterification from derivatives 1 and 2, respectively.
The syntehsis of novel N-aryl 3-hydroxypyridin-4-ones, 3-hydroxy-1-phenylpyridin-4-one
(8) and 3-hydroxy-1-(p-methoxyphenyl)pyridin-4-one (9) was described in the second part of the
thesis. Compounds 8 and 9 were prepared from modified kojic acid (derivatives 6 and 7) and
selected arylamines, aniline and p-methoxyaniline. Acetylated mannosyl derivatives 10 and 11
were prepared next from pyridinones 8 and 9 by Koenigs-Knorr method followed by subsequent
deacetylation using Zemplén procedure which afforded deprotected mannosylated derivatives 12
and 13, respectively.
The structures of all compounds were elucidated by NMR spectroscopy (1H, 13C) and mass
spectrometry (MS).

• Keywords: adamantan-1-iloctena kiselina; Koenigs-Knorrova metoda glikozidacije; kojična kiselina; manoza; N-aril-3-hidroksipiridin-4-oni; Steglichova esterifikacija
• Keywords (english): adamantan-1-ylacetic acid; Koenigs-Knorr glycosylation method; kojic acid; mannose; N-aryl-3-hydroxypiridin-4-ones; Steglich esterification
• Language: croatian
• URN:NBN: urn:nbn:hr:217:221715
• 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: 2018-12-15
• Created on: 2017-03-22 09:59:07