Summary
The hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles1a–d with enol ethers2a–c yieldscis/trans diastereoisomers of 2-alkoxy-4,6-diaryl-3,4-dihydro-2H-pyran-5-carbonitriles3 and4 in 79–98% yield. The similar reaction of1a–c with cyclic enol ether5 affords diastereoisomeric cycloadducts6 and7 withcis annulated pyran rings. Reaction of3 with sulfuric acid leads to 2-hydroxy-3,4-dihydro-2H-pyran-5-carbonitriles8 and9.
Zusammenfassung
Die Hetero-Diels-Alder-Reaktion der 3-Aryl-2-benzoyl-2-propennitrile1a–d mit den Enolethern2a–c ergibt diecis/trans-diastereomeren 2-Alkoxy-4,6-diaryl-3,4-dihydro-2H-pyran-5-nitrile3 und4 in einer Ausbeute von 79–98%. Dieselbe Reaktion von1a–c mit dem cyclischen Enolether5 liefert die diastereomeren Cycloaddukte6 und7 mitcis-anellierten Pyranringen. Reaktion von3 mit Schwefelsäure führt zu den 2-Hydroxy-3,4-dihydro-2H-pyran-5-nitrilen8 und9.
Similar content being viewed by others
References
Tietze LF, Harfiel U, Hubsch T, Voss E, Wichmann J (1991) Chem Ber124: 881
Tietze LF (1983) Ang Chem Int Edn Engl22: 828
Tietze LF, Voss E, Herms K, Sheldrick GM (1985) Tetrahedron Lett26: 5273
Tietze LF (1974) Chem Ber107: 2491;
Desimoni G, Tacconi G (1975) Chem Rev75: 651
Tietze LF, Fennen J, Wichmann J (1992) Chem Ber125: 1507
John AR, Schmidt V, Wyler H (1987) Helv Chim Acta70: 600
Zhuo JC, Wyler H (1995) Helv Chim Acta78: 151
Bogdanowicz-Szwed K, Pałasz A (1995) Monatsh Chem126: 1341
Kauffmann K (1951) Chem Ber50: 527;
Nazario M, Quinteiro M, Seoane C, Soto JL (1987) Rev R Acad Cienc Exactas18: 281
Jackmann LM, Sternhel S (1969) Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd edn. Pergamon Press
Uray G, Wolbeis OS, Junek H (1979) J Mol Struct54: 77
Bushweller CH, O'Neil JW (1969) Tetrahedron Lett 4713
Johnstone RAW, Malkolm ER (1996) Mass Spectromerty for Chemists and Biochemists. Cambridge University Press
Kirby AJ (1983) Anomeric Effect and Related Stereoelectronic Effects of Oxygen, chapter 2. Springer, Berlin Heidelberg New York Tokyo
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bogdanowicz-Szwed, K., Pałasz, A. Hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles with enol ethers. Synthesis of 2-alkoxy-3,4-dihydro-2H-pyran-5-carbonitriles. Monatsh Chem 128, 1157–1172 (1997). https://doi.org/10.1007/BF00807566
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00807566