Synthesis of 5-Aroyl-2-aryl-3-hydroxypyridin-4(1<i>H</i>)-ones

Abstract

A two-stage synthesis of 5-aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones (56–66% overall yields) was carried out by refluxing 5-aroyl-3-(benzyloxy)-2-(het)aryl-4H-pyran-4-ones with ammonium acetate in AcOH and subsequent debenzylation. The prepared N-unsubstituted 4-pyridones exist in the pyridone tautomeric form.

Keywords

• 3-hydroxy-4-pyridones
• 4-pyrones
• debenzylation
• metalloenzyme inhibitors
• chelating agents
• tautomerism