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

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… Click to show full 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: dioxoimidazolidin ide; potassium dioxoimidazolidin; three component; synthesis arylidene

Journal Title: Current Organic Chemistry
Year Published: 2021

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