Abstract
The reaction of different 7,8-substituted coumarin 4-acetic acids with 7-diethylaminocoumarin-3-carbaldehyde in the presence of piperidine in methanol gives 1,2-biscoumarinylethenes. These compounds undergo regiospecific Diels–Alder reactions at their electron-rich diene components C<sub>3</sub>–C<sub>4</sub>–C<sub>10</sub>–C<sub>9</sub>, with electron-deficient dienophiles. The feasibility of normal electron-demand Diels–Alder reactions could be explained on the basis of the HOMO–LUMO gap. All the compounds are new and are intensely colored.
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