Background:
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.
Objective:
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.
Methods:
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.
Results:
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.
Conclusion:
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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.