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

Silva, V. L. M., Silva, A. M. S., Pinto, D. C. G. A., Cavaleiro, J. A. S., Vasas, A., Patonay, T.: Syntheses of (E)- and (Z)-3-styrylchromones.
Monatsh. Chem. 139, 1307-1315, 2008.

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Journal metrics:

Q2 Chemistry (miscellaneous)

title:

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

authors:

Silva, Vera L. M.
Silva, Artur M. S.
Pinto, Diana C. G. A.
Cavaleiro, José A. S.
Vasas Attila
Patonay Tamás

published:

2008

type:

article

genre:

research article/review article

journal:

Monatshefte für Chemie (ISSN: 0026-9247)

language:

English

HAC:

Natural Sciences, Chemical Sciences

subjects:

chromone-3-carboxaldehyde, 3-styrylchromones, Wittig reaction, knoevenagel condensation, microwave irradiation

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.