Fast and Efficient Synthesis of 4‐Arylidene‐3‐phenylisoxazol‐5‐ones

Abstract

A convenient and easy synthesis of 4-arylidene-3-phenylisoxazol-5-ones by the three-component reaction of hydroxylamine, ethyl benzoylacetate and aromatic aldehydes in the presence of DABCO in refluxing ethanol is reported.

Boric acid-catalyzed multi-component reaction for efficient synthesis of 4H-isoxazol-5-ones in aqueous medium

“…If necessary, further purification was performed by recrystallization from suitable solvents such as EtOH to give the desired compounds in high yields. The products are known and their identity was confirmed by comparison of their physical and spectroscopic data with those available in recent papers [31][32][33][34][35][36][37][38].…”

“…With this methodology as background, we attempted to develop an alternative catalyst for the preparation of arylmethylene isoxazol-5(4H)-ones. Although 4H-isoxazol-5-ones have so far been synthesized [31][32][33][34][35][36][37][38], to the best of our knowledge, no reports that include the use of boric acid for condensation of aromatic aldehydes (1), b-ketoesters (3), and hydroxylamine hydrochloride (2) have been reported. We here report the preparation of 4H-isoxazol-5-ones (4a-x) by one-pot three-component condensation of aryl aldehydes (1), hydroxylamine hydrochloride (2), and ethyl 3-oxobutanoate (3a)/ethyl 4-chloro-3-oxobutanoate (3b)/ethyl 3-oxo-3-phenylpropanoate (3c) using boric acid, H 3 BO 3 , as a green and reusable catalyst in water at room temperature (Scheme 1).…”

Recent Advance in Development of 3-Methyl-4-Arylmethylene Isoxazole-5(4h)-Ones and 6-Amino-1,4-Dihydropyrano[2,3-C]-Pyrazole-5-Carbonitriles: Synthetic Applications and Pathways

“…[45] www.wjpps.com Kiyani and co-workers (Scheme 14). [46] Different solvents such as ethanol, 1,4-dioxane, hexane, water and acetone were also considered in this reaction by the authors, although best results were obtained in water in terms of product yield and reaction time.…”

Modification, Characterization, and Catalytic Application of Mesolite for One Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones

“…25 , 12 (1), 2017, 35 Copyright © 2017, BCREC, ISSN 1978-2993 nated mesolite shows low intensity due to loss of crytallinity and leaching of aluminum from framework, but both the samples are in orthorhombic phase.…”

“…Furthermore, isoxaole derivatives act as fluorescent chemosensor for fluoride aninon [19]. Hence by considering importance and applications of isoxaole derivatives several catalytic methods have been developed using homogenous and heterogeneous catalyst like potassium phthalimide [20], n-bromosuccinimide [21], sodium oxalate, tetra-butylammonium perchlorate, glycine [22], Tartaric acid [23], boric acid [24], DABCO [25], sodium benzoate [26], nano-Fe2O3 [27], and H3PW11CuO40 [28]. However, some of them suffered from some problems like harsh reaction condition, long reaction time, low yield and tedious work up for separation of catalyst which generate acidic effluent.…”