Preparation of pyridinium-based ionic liquid and application as a green catalyst for the synthetic route of 4H-1-benzopyran-5(6H)-ones
Authors:   Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University - Ho Chi Minh City,Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam, Dao Huong Ngoc Thi ,   Vietnam National University - Ho Chi Minh City, Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam, Nguyen The Thai ,   Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University - Ho Chi Minh City,Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam,   Vietnam National University - Ho Chi Minh City, Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam, Nguyen Tran Huyen Thi ,   Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University - Ho Chi Minh City,Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam,   Vietnam National University - Ho Chi Minh City, Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam, Phan Thuy Hong Ngoc ,   Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University - Ho Chi Minh City,Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam,   Vietnam National University - Ho Chi Minh City, Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam, Tran Phuong Hoang ,   Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University - Ho Chi Minh City,Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam,   Vietnam National University - Ho Chi Minh City, Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Vietnam
Published: March 2024

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. Anew 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.