Asiyeh Mosallanezhad and Hamzeh Kiyani
Apr 24, 2019
Citations
0
Influential Citations
23
Citations
Journal
Current Organocatalysis
Abstract
4-Arylmethylideneisoxazol-5(4H)-ones are a class of organic compounds with a variety of applications in the agriculture, filter dyes, photonic devices, and pharmaceutical industries. They are also used as synthetic precursors for the synthesis of other organic compounds. As a result, efforts are being made to search new and available catalyst and green methods toward their synthesis. The aim of this work is to investigate the catalytic activity of salicylic acid as an inexpensive, easy to handle, and safe catalyst to synthesis of some derivatives of isoxazole-5(4H)-ones in water medium. To aqueous solution of equal amounts of aryl/heteroaryl aldehydes, β-ketoesters, and hydroxylamine hydrochloride; salicylic acid (15 mol%) was added and the reaction mixture was stirred at room temperature for a specified periods. The precipitated product was filtered and washed with water to obtain 3-substituted-4-arylmethylideneisoxazol-5(4H)-ones. The reaction conditions were also optimized and extended to synthesis other isoxazol-5(4H)-ones. The salicylic acid is found to possess acceptable catalytic activity for the promotion of three-component cyclocondensation of aryl/heteroaryl aldehydes, β-ketoesters, and hydroxylamine hydrochloride. The three-component reaction led to construction of 3-substituted-4-arylmethylideneisoxazol- 5(4H)-ones in good to high isolated reaction yields. The efficient and environmental friendliness procedure for the synthesis of isoxazol- 5(4H)-ones is introduced. The reaction also carried out smoothly in water as a cost-effective, simple, green, and non-toxic solvent at room temperature without using heating, microwave, and ultrasound sources.