Abstract

The synthesis of some novel diethyl {(4-oxo-1,4-dihydroquinolin-3-yl)(aryl/heteroaryl-amino)methyl}phosphonates, was achieved. The methodology is based on one-pot three-component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (1), amine, and diethyl phosphite in the presence of CdI₂ nanoparticles as an efficient catalyst under conventional heating at 80 °C or ultrasound irradiation at 50 °C. The mild reaction conditions, operational simplicity, and excellent yields are the essential advantages of this protocol. Most of the products recorded inhibitory effects toward plant pathogenic fungi nearly to the standard control. The hybridization between diethyl α-aminophosphonate and quinolin-4-one moieties clubbed with sulfonamide, antipyrine, or 1,2,4-triazine in one molecular frame displayed good antifungal activities.

摘要

合成了一些新型的{(4-氧代-1,4-二氢喹啉-3-基)(芳基/杂芳基氨基)甲基}膦酸二乙酯。该方法基于 4-氧代-1,4-二氢喹啉-3-甲醛 ( 1 )、胺和亚磷酸二乙酯在 CdI ₂存在下的一锅三组分反应纳米颗粒在 80 °C 的常规加热或 50 °C 的超声波照射下作为有效的催化剂。反应条件温和、操作简单、收率优异是该方案的本质优势。大部分产品对植物病原真菌的抑制效果接近标准对照。α-氨基膦酸二乙酯和喹啉-4-酮部分与磺酰胺、安替比林或1,2,4-三嗪在一个分子框架中的杂交显示出良好的抗真菌活性。