Abstract:

A series of 2-substituted-2,3-dihydro-4(1H)-quinazolinones derivatives were synthesized efficiently by the cyclocondensation of 2-anthranilamide with an aldehyde or ketone in the presence of aluminum chloride in water at 60 ℃ after grinding at room temperature. The catalytic activity of different catalysts was compared. The effects of the amount of catalyst and the amount of solvent on the yields were investigated. The results show that the best reaction results could be obtained when the molar ratio of 2-anthranilamide to an aldehyde or ketone is 1∶1, the amount of catalyst is 1% (based on the mole of reactant), and water is 2 mL. The structures of products were characterized by IR, 1H-NMR, mass spectrum and elemental analysis. The probable catalytic mechanism for the reaction was proposed.

Key words:

2,3-Dihydro-4(1H)-quinazolinones,    , Aluminum chloride,    ,  2-Anthranilamide,   ,  Aldehydes,    ,  Ketonesmso-ascii-font-family: Calibri, mso-ascii-theme-font: minor-latin, mso-fareast-font-family: 宋体, mso-fareast-theme-font: minor-fareast, mso-hansi-font-family: Calibri, mso-hansi-theme-font: minor-latin">

摘要： 在氯化铝催化作用下, 以水为溶剂, 将2-氨基苯甲酰胺和醛/ 酮室温研磨后, 温度为60 ℃时加热反应, 可有效环化合成一系列2-取代-2 , 3 -二氢-4(1H)-喹唑啉酮衍生物。比较不同催化剂的催化活性, 考察了催化剂和水的用量对收率的影响。结果表明, 在n(2-氨基苯甲酰胺)/n(醛/ 酮)=1 ∶1, 催化剂摩尔分数为1 %, 水体积2 m L 的反应条件下, 实验结果最好。产品结构经IR, 1H -NM R, 质谱, 元素分析进行表征, 并提出可能的催化反应机理。

关键词: 2, 3 -二氢-4(1H)-喹唑啉酮 , 氯化铝 , 2 -氨基苯甲酰胺 , 醛 , 酮