Hetero-<Emphasis Type="Italic">Diels-Alder</Emphasis> reaction of propenenitriles with enol ethers: a convenient approach to functionalized 3,4-dihydro-2<Emphasis Type="Italic">H</Emphasis>-pyrans |
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Authors: | Aleksandra Pałasz Krystyna Bogdanowicz-Szwed |
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Institution: | (1) Department of Organic Chemistry, Jagiellonian University, Kraków, Poland |
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Abstract: | The hetero-Diels-Alder reaction of 3-(N-acetyl-N-benzylamino)-2-formylprop-2-enenitrile with enol ethers yielded cis/trans diastereoisomers of 2-alkoxy-4-amino-3,4-dihydro-2H-pyran-5-carbonitriles in moderate yields. Acidic hydrolysis of cis-diastereoisomer in concentrated sulfuric acid gave 2-oxo-1,2-dihydropyrydine-3-carbaldehyde. The reaction of 2-benzoyl-3-heteroaromaticprop-2-enenitriles
with enol ethers afforded diastereoisomeric cis/trans cycloadducts in good yields. The structure of the products is discussed in terms of configuration and preferred conformation.
Correspondence: Aleksandra Pałasz, Department of Organic Chemistry, Jagiellonian University, Kraków, Poland. |
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Keywords: | Diels-Alder reaction Pyrans α β -Unsaturated carbonyl compounds Enol ethers |
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