Three-component reaction between kojic acid and acyl chlorides with potassium selenocyanate: synthesis of 2-aryl(alkyl)-6-hydroxymethyl-4-selenoxo-4H-pyrano[2,3-e][1,3]oxazin-8-one

Abstract

We report an efficient method for the synthesis of 2-aryl(alkyl)-6-hydroxymethyl-4-selenoxo-4H-pyrano[2,3-e][1,3]oxazin-8-ones from the condensation of potassium selenocyanate and acyl chlorides with kojic acid in the presence of catalytic amounts of N-methylimidazole under solvent-free conditions. This new protocol offers advantages such as mild reaction conditions, short reaction time, easy work-up, and high yields of biologically active products and does not involve any hazardous solvent. This prompted us to establish a novel oxazine ring formation method to find promising bioactive oxazine compounds. They are found to have exhibit diverse pharmacological properties.

Keywords:

• Kojic acid
• acyl chlorides
• potassium selenocyanate
• N-methylimidazole
• 2-aryl(alkyl)-6-hydroxymethyl-4-thioxo-4H-pyrano[23-e][13]oxazin-8-ones
• solvent-free conditions

Disclosure statement

No potential conflict of interest was reported by the authors.