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Synthesis of functionalized 3,4-dihydro-2H-pyrans by hetero —Diels-Alder reaction of an enaminoketone with enol ethers

Synthese funktionalisierter 3,4-Dihydro-2H-pyrane durch Hetero —Diels-Alder — Reaktion eines Enaminoketons mit Enolethern

  • Organische Chemie Und Biochemie
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Summary

The hetero —Diels-Alder reaction of 3-(N-acetylbenzylamino)-2-cyano-1-phenyl-2-propen-1-one (3) with enol ethers (4) leads to diastereoisomeric cycloadducts5 and6 in good yields. The structure of the products is discussed in terms of configuration and preferred conformation. Reaction of5 with sulfuric acid yields 3-benzoyl-1,2-dihydropyridin-2-one (7).

Zusammenfassung

Die Hetero —Diels-Alder — Reaktion von 3-(N-Acetylbenzylamino)-2-cyano-1-phenyl-2-propen-1-on (3) mit Enolethern (4) führt in guten Ausbeuten zu den diastereomeren Cycloaddukten5 und6. Die Strukturen der Produkte werden im Zusammenhang mit ihrer Konfiguration und Vorzugskonformation diskutiert. Die Reaktion von5 mit Schwefelsäure liefert 3-Benzoyl-1,2-dihydropyridin-2-on (7).

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Authors and Affiliations

  1. Department of Organic Chemistry, Jagiellonian University, PL-30060, Kraków, Poland

    K. Bogdanowicz-Szwed & A. Pałasz

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  1. K. Bogdanowicz-Szwed
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  2. A. Pałasz
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Bogdanowicz-Szwed, K., Pałasz, A. Synthesis of functionalized 3,4-dihydro-2H-pyrans by hetero —Diels-Alder reaction of an enaminoketone with enol ethers. Monatsh Chem 126, 1341–1348 (1995). https://doi.org/10.1007/BF00807063

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  • DOI: https://doi.org/10.1007/BF00807063

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