Syntheses of (<Emphasis Type="Italic">E</Emphasis>)- and (<Emphasis Type="Italic">Z</Emphasis>)-3-styrylchromones |
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Authors: | Vera L M Silva Artur M S Silva Diana C G A Pinto José A S Cavaleiro Attila Vasas Tamás Patonay |
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Institution: | (1) Chemistry Department and QOPNA, University of Aveiro, Aveiro, Portugal;(2) Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary |
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Abstract: | Several (E)- and (Z)-3-styrylchromones were prepared by two different methodologies, the Wittig reaction of chromone-3-carboxaldehyde with benzylic ylides and the Knoevenagel condensation of chromone-3-carboxaldehyde with phenylacetic acids in the presence of potassium tert-butoxide under microwave irradiation. The Knoevenagel reaction followed by a decarboxylation offered an efficient and diastereoselective method for preparing (E)-3-styrylchromones in a shorter reaction time. It was also demonstrated that phenylacetic acid can also be substituted with
success by phenylmalonic acid. The stereochemistry of all products was assigned by NMR experiments.
Correspondence: Artur M. S. Silva, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal. |
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Keywords: | Chromone-3-carboxaldehyde 3-Styrylchromones Wittig reaction Knoevenagel condensation Microwave irradiation |
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