Summary.
The reaction of benzoylacetonitrile, methyl cyanoacetate, and ethyl benzoylacetate with 2-allyloxy- and 2-(3-methyl-2-butenyloxy)-benzaldehyde as well as 2-(3-methyl-2-butenyloxy)-1-naphthaldehyde afforded the corresponding Knoevenagel condensation products. Some of those underwent spontaneous intramolecular cycloaddition to give cis-fused 2H-pyran derivatives as major products. One-pot reactions of 1,3-cyclohexanedione and 5,5-dimethyl-1,3-cyclohexanedione with 2-(3-methyl-2-butenyloxy)-benzaldehyde and 2-(3-methyl-2-butenyloxy)-1-naphthaldehyde resulted in Diels-Alder cycloadducts.
Zusammenfassung.
Reaktion von Benzoylacetonitril, Methylcyanoacetat and Ethylbenzoylacetat mit 2-Allyloxy- und 2-(3-Methyl-2-butenyloxy)-benzaldehyd sowie mit 2-(3-Methyl-2-butenyloxy)-1-naphthaldehyd ergab das entsprechende Knoevenagel-Derivat. Einige dieser letzteren Produkte unterlagen einer spontanen intramolekularen Cycloaddition zu cis-verknüpfen 2H-Pyranderivaten als Hauptprodukt. Eintopfreaktionen von 1,3-Cyclohexandion und 5,5-Dimethyl-1,3-cyclohexandion mit 2-(3-Methyl-2-butenyloxy)-benzaldehyd und 2-(3-Methyl-2-butenyloxy)-1-naphthaldehyd resultierten in Diels-Alder-Cycloaddukten.
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Received November 2, 1998. Accepted November 19, 1998
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Bogdanowicz-Szwed, K., Pałasz, A. Intramolecular Hetero-Diels-Alder Reactions of Functionalized α, β-Unsaturated Carbonyl Compounds: Polycyclic 2H-Pyran Derivatives. Monatshefte fuer Chemie 130, 795–807 (1999). https://doi.org/10.1007/PL00010261
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DOI: https://doi.org/10.1007/PL00010261