制备吡啶基离子液体并将其用作 4H-1-苯并吡喃-5(6H)-酮合成路线的绿色催化剂

Huong Ngoc Thi Dao, T. Nguyen, Tran Huyen Thi Nguyen, Thuy Hong Ngoc Phan, Phuong Hoang Tran
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引用次数: 0

摘要

通过简单的方法合成了 1-(4-磺丁基)吡啶鎓氯锌酸盐离子液体,收率高达 89%,并利用傅立叶变换红外光谱、核磁共振和 HRMS 光谱对其进行了表征。利用制备的离子液体催化剂,该一锅反应被用于苯甲醛、5,5-二甲基-1,3-环己二酮和二氰基甲烷的缩合反应。催化剂负载量为 10 摩尔%、水和乙醇(1:1, v/v)混合溶剂、温度保持在 100°C 下 180 分钟时,反应达到最佳条件。制备出的苯并吡喃-5(6H)-酮衍生物谱系广泛,结果中等至良好。该方法的显著特点包括底物易得、反应时间短、使用环保溶剂,以及在分离产物时无需使用色谱法。在 2-氨基-3-氰基-4-苯基-7,7-二甲基-7,8-二氢-4H-1-苯并吡喃-5(6H)-酮的合成过程中,成功合成了一种新的酸性吡啶基离子液体,并将其用作催化剂。这些反应涉及芳香族苯甲醛、5,5-二甲基-1,3-环己二酮和二氰基甲烷在乙醇和水的混合溶剂中的缩合反应,以中等至良好的收率得到所需的产物。该方法既高效又环保,而且可以通过重结晶轻松获得产物。因此,该方法是现有方法的一种替代方案。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Preparation of pyridinium-based ionic liquid and application as a green catalyst for the synthetic route of 4H-1-benzopyran-5(6H)-ones
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.
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