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Syntheses of (E)- and (Z)-3-styrylchromones

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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.

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Authors and Affiliations

  1. Chemistry Department and QOPNA, University of Aveiro, Aveiro, Portugal

    Vera L. M. Silva, Artur M. S. Silva, Diana C. G. A. Pinto & José A. S. Cavaleiro

  2. Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

    Attila Vasas & Tamás Patonay

Authors
  1. Vera L. M. Silva
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  2. Artur M. S. Silva
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  3. Diana C. G. A. Pinto
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  4. José A. S. Cavaleiro
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  5. Attila Vasas
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  6. Tamás Patonay
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Corresponding author

Correspondence to Artur M. S. Silva.

Additional information

Correspondence: Artur M. S. Silva, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal.

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Silva, V., Silva, A., Pinto, D. et al. Syntheses of (E)- and (Z)-3-styrylchromones. Monatsh Chem 139, 1307–1315 (2008). https://doi.org/10.1007/s00706-008-0926-0

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  • DOI: https://doi.org/10.1007/s00706-008-0926-0

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