Reakce 3-chlorchinolin-2,4-dionů s aminoalkoholy

Bc. Hana Křemenová

Master's thesis

Reactions of 3-Chloroquinoline-2,4-diones with Aminoalcohols

Abstract:

Diplomová práce se zabývá studiem reakcí derivátů 3-chlorchinolin-2,4(1H,3H)-di-onů s ethanolaminem v N,N'-dimethylformamidu, při nichž byly úspěšně získány předpo-kládané produkty 3-(hydroxyethylamino)chinolin-2,4(1H,3H)-diony. Ty byly následně po-drobeny dalšímu zkoumání. Reakcemi s kyanatanem draselným byly získávány produkty v závislosti na substituci v polohách 1 a 3 na chinolinovém skeletu, konkrétně 2,6-dihydroimi-dazo[1,5-c]-chinazolin-3,5-dion, 3-(3'-hydroxyethylureido)-2-oxo-2,3-dihydro-indoly a 3-hydroxyethylspiro[imidazolidin-5,3´-indol]-2,2´-diony. Při reakci s trifosgenem byla snaha získat novou sloučeninu 3-(2-oxooxazolidin-3-yl)chinolin-2,4(1H,3H)-dionu, která se podařila izolovat z jedné vyzkoušené reakce.

Abstract:

This master thesis studies the reactions of derivatives of 3-chloroquinoline-2,4(1H, 3H)-diones with ethanolamine in N,N'-dimethylformamide, in which the assumed products of 3-(hydroxyethylamino)quinoline-2,4(1H,3H)-diones have been successfully obtained. They were subsequently subjected to a series of reactions. During the reactions with potas-sium cyanate were obtained products depending on the substitution at positions 1 and 3 on the quinoline skeleton, namely 2,6-dihydroimidazo[1,5-c]-quinazoline-3,5-dione, 3-(3'-hyd-roxyethylureido)-2-oxo-2,3-dihydro-indole and 3-hydroxyethylspiro[imidazolidine-5,3'-in-dol]-2,2'-dione. In the reaction with triphosgene was an effort to obtain the novel compound 3-(2-oxo-oxazolidin-3-yl)-quinoline-2,4(1H,3H)-dione, which was successful isolate from the one tested reaction.

Keywords

Nukleofilní substituce, 3-chlorchinolin(1H, 3H)-2, 4-dion, ethanolamin, 3-(hydroxyethylamino)-1H, 3H-chinolin-2, kyanatan draselný, trifosgen.

Language used: Czech

Date on which the thesis was submitted / produced: 13. 5. 2016

Accessible from:: 13. 5. 2016

Thesis defence

• Date of defence: 8. 6. 2016

Tomas Bata University in Zlín

Faculty of Technology

Master programme / field:
Chemistry and Food Technologies / Food Chemistry and Chemistry of Bioactive Substances