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Current Organic Chemistry

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ISSN (Online): 1875-5348

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Research Article

Three-component Synthesis of 4-Arylidene-3-alkylisoxazol-5(4H)-ones in the Presence of Potassium 2,5-dioxoimidazolidin-1-ide

Author(s): Neda Reihani and Hamzeh Kiyani*

Volume 25, Issue 8, 2021

Published on: 12 February, 2021

Page: [950 - 962] Pages: 13

DOI: 10.2174/1385272825666210212120517

Price: $65

Abstract

An efficient synthesis of 4-arylidene-3-alkylisoxazole-5(4H)-ones has been implemented via the three-component cyclocondensation of aryl(heteroaryl)aldehydes with hydroxylamine hydrochloride and β-ketoesters. The potassium 2,5-dioxoimidazolidin-1-ide has been introduced as the new organocatalyst to facilitate this heterocyclization. In the current process, three starting materials, including substituted benzaldehydes/heterocyclic aromatic aldehydes, hydroxylamine hydrochloride, and ethyl acetoacetate/propyl acetoacetate/butyryl acetoacetate have been successfully used to synthesize the number of substituted isoxazole- 5(4H)-ones in good to high yields in ethylene glycol as a green reaction medium at 80 ºC. The low catalyst loading is also a main advantage over some reported catalysts.

Keywords: 4-Arylidene-3-alkylisoxazole-5(4H)-ones, potassium 2, 5-dioxoimidazolidin-1-ide, green chemistry, aryl aldehyde, hydroxylamine hydrochloride, β-dicarbonyl.

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