Solid-Phase synthesis of precursors of bisheterocyclic derivatives of 3-hydroxy-4(1H)-quinolinone.
The main target of this work was preparation of the precursors leading to the new type of 3-hydroxy-4-(1H)-quinolinone derivatives, compounds with potential biological importance. In this regard, we first focused our attention on the synthesis of intermediates resulting in the connection of the heterocycle and hydroxyquinoline skelet in position 7 via spacer with amide group. For this purpose we prepared a model intermediate methyl 4-((3-hydroxypropyl)carbamoyl)-2-nitrobenzoate using the solid-phase synthesis. Later, we worked on the successful conversion of hydroxy group of model intermediate to primary or secondary amino group. After synthesis of target intermediate, we tried to prepare a model bisheterocycle of hydroxyquinoline-thiazole. Unfortunately, the attempt was not successful and it will be necessary to focus on optimisation of the final reaction step.
Stav:
Absolvoval od 2006 do 2009.