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

DOI: 10.1007/BF00807566

Source and publish data:

Monatshefte fur Chemie p. 1157 - 1172 (1997)

Update date:2022-08-03

Topics:

Authors:

Bogdanowicz-Szwed

Palasz Palasz

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Article abstract of DOI:10.1007/BF00807566

The hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles 1a-d with enol ethers 2a-c yields cis/trans diastereoisomers of 2-alkoxy-4,6-diaryl-3,4-dihydro-2H-pyran-5-carbonitriles 3 and 4 in 79-98% yield. The similar reaction of 1a-c with cyclic enol ether 5 affords diastereoisomeric cycloadducts 6 and 7 with cis annulated pyran rings. Reaction of 3 with sulfuric acid leads to 2-hydroxy-3,4-dihydro-2H-pyran-5-carbonitriles 8 and 9.

Full text of DOI:10.1007/BF00807566

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