Br鰊sted酸离子液体催化2-芳基-2,3-二氢-4(1H)-喹啉酮的简便合成

Facile Synthesis of 2-Aryl-2,3-dihydro-4(1H)-quinolinones Catalyzed by Br鰊sted Acidic Ionic Liquid

摘要:

制备了三种Br鰊sted酸离子液体：1-甲基-3-(3-磺丙基)咪唑硫酸氢盐([SO3H-pmim]HSO4)、1-(3-磺丙基)吡啶硫酸氢盐([SO3H-ppy]HSO4)、N-(3-磺丙基)三乙基铵硫酸氢盐([SO3H-ptea]HSO4)，用于催化邻氨基苯乙酮和芳香醛的反应一锅法合成2-芳基-2,3-二氢-4(1H)-喹啉酮，考察了它们的催化活性和重复使用性能。结果表明，三种离子液体对邻氨基苯乙酮和芳香醛的反应均具有较高的催化活性，以[SO3H-ptea]HSO4催化性能更好。在60 ℃和无溶剂条件下，[SO3H-ptea]HSO4可以有效催化邻氨基苯乙酮和不同芳香醛反应，以68.3%～95.1%的收率得到目标化合物。离子液体经真空干燥重复使用5次，催化活性无明显下降。

Abstract:

Three Br鰊sted acidic ionic liquids including 1-methyl-3-(3-sulfopropyl)imidazolium hydrogen sulfate([SO3H-pmim]HSO4), 1-(3-sulfopropyl)pyridinium hydrogen sulfate([SO3H-ppy]HSO4) and N-(3-sulfopropyl)triethylammonium hydrogen sulfate([SO3H-ptea]HSO4) were synthesized. A one-pot reaction of o-aminoacetophenone and aromatic aldehydes in the presence of ionic liquid as an effective catalyst for the synthesis of 2-aryl-2,3-dihydro-4(1H)-quinolones was described. The activity and reusability of ionic liquid as catalyst for reaction of o-aminoacetophenone and aromatic aldehydes were investigated. The ionic liquids exhibited high catalytic activity and good reusability for reaction of o-aminoacetophenone and aromatic aldehydes, and the catalytic performance of [SO3H-ptea]HSO4 could be much better than that of others. The reaction of o-aminoacetophenone and aromatic aldehydes catalyzed by [SO3H-ptea]HSO4 could proceed well to desired product in 68.3%～95.1% yields under the conditions of solvent-free and reaction temperature 60 ℃. The ionic liquid was reused at least five times without significant decrease in activity after drying under vacuum.