Synthesis of 1,2,3-triazole derivatives of pyran-4-ones from meta and para-nitrophenyl azides and their biological activity

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).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)