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Efficient synthesis of 6-aryl-4-trifluoromethyl/ethoxycarbonyl-2 H -pyran-2-ones through self-condensation of penta-2,4-dienenitriles

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Abstract An efficient synthesis of two new series of 6-aryl-4-trifluoromethyl-2H-pyran-2-ones and 6-aryl-4-carboxyethyl-2H-pyran-2-ones, obtained through the self-condensation reaction of 5-aryl-5-methoxy-3-(trifluoromethyl)penta-2,4-dienenitriles 3 and ethyl 4-aryl-2-(cyanomethylene)-4-methoxybut-3-enoates 4 respectively, is reported. The self-condensation reaction… Click to show full abstract

Abstract An efficient synthesis of two new series of 6-aryl-4-trifluoromethyl-2H-pyran-2-ones and 6-aryl-4-carboxyethyl-2H-pyran-2-ones, obtained through the self-condensation reaction of 5-aryl-5-methoxy-3-(trifluoromethyl)penta-2,4-dienenitriles 3 and ethyl 4-aryl-2-(cyanomethylene)-4-methoxybut-3-enoates 4 respectively, is reported. The self-condensation reaction of the enoates 4 was performed in water in the presence of hydrochloric acid whereas the self-condensation reaction of the penta-2,4-dienenitriles 3 required the use of zinc bromide and hydrochloric acid in order to give the respective 2H-pyran-2-ones. Products were obtained up to 97% yield.

Keywords: efficient synthesis; pyran ones; penta dienenitriles; self condensation

Journal Title: Tetrahedron Letters
Year Published: 2018

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