Affiliation:
1. School of Chemistry, Damghan University, Damghan, Iran
Abstract
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.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Analytical Chemistry,Catalysis
Cited by
32 articles.
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