Preparation of pyridinium-based ionic liquid and application as a green catalyst for the synthetic route of 4<i>H</i>-1-benzopyran-5(6<i>H</i>)-ones

Abstract

1-(4-sulfobutyl)pyridinium chlorozincate ionic liquid was synthesised in high yield (89%) through a simple route and characterised using FT-IR, NMR, and HRMS spectroscopy. The one-pot reaction was employed for the condensation reaction of benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane, utilising the prepared ionic liquid catalyst. The optimal conditions for the reaction were achieved with a catalyst loading of 10 mol%, a solvent mixture of water and ethanol (1:1, v/v), maintained at 100°C for 180 minutes. A broad spectrum of benzopyran-5(6H)-one derivatives was prepared, yielding moderate to good results. The notable features of this procedure include readily available substrates, short reaction times, the use of environmentally friendly solvents, and the elimination of the need for chromatography in the isolation of products. A new acidic pyridinium-based ionic liquid was successfully synthesised and used as a catalyst in the synthetic process of 2-amino-3-cyano-4-phenyl-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-5(6H)-ones. These reactions involved a condensation reaction of aromatic benzaldehydes, 5,5-dimethyl-1,3-cyclohexanedione, and dicyanomethane in a solvent mixture of ethanol and water, resulting in the desired products in moderate to good yields. The procedure is efficient and eco-friendly, and the products can be easily obtained by recrystallisation. Thus, this protocol offers an alternative to existing methods.

Keywords

• Brønsted-Lewis acidic ionic liquid
• green catalyst
• multicomponent reaction
• 1-(4-sulfobutyl) pyridinium chlorozincate
• 4H-1-benzopyran-5(6H)-one