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).

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).