Brnsted酸离子液体催化合成2-芳基-2,3-二氢-4(1H)-喹啉酮

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

制备了3种Brnsted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,3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。

Three Bronsted acidic ionic liquids including 1-methyl-3-（3-sulfopropyl）imidazolium hydrogen sulfate （ [ SO3H-pmim ] HSO4 ）, 1 - （ 3-sulfopropyl ） pyridinium hydrogen sulfate （ [ SO3 H-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 the reaction between o-aminoacetophenone and aromatic aldehydes were investigated. The ionic liquids exhibited high catalytic activity and good reusability for the reaction between o-aminoacetophenone and aromatic aldehydes, and the catalytic performance of [ SO3H-ptea ] HSO4 was much better than that of others. The reaction of o- aminoacetophenone and aromatic aldehydes catalyzed by [ SO3H-ptea] HSO4 proceeded well to give the desired product in the yields of 68.3% - 95.1% under the conditions of no solvent and reaction temperature of 60 ~C. The ionic liquid was reused at least five times without significant decrease in activity after drying under vacuum.