Efficient synthesis of 6-aryl-4-trifluoromethyl/ethoxycarbonyl-2H-pyran-2-ones through self-condensation of penta-2,4-dienenitriles |
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Authors: | Mário A. Marangoni Carlos E. Bencke Helio G. Bonacorso Marcos A.P. Martins Nilo Zanatta |
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Affiliation: | 1. Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, Brazil;2. Laboratory of Chemistry, Instituto Federal Catarinense, 89240-000 São Francisco do Sul, SC, Brazil |
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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 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. |
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Keywords: | Penta-2,4-dienenitriles Enones Self-condensation reaction Pyran-2-ones 2-Pyranones |
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