91025-00-2Relevant academic research and scientific papers
Hetero-Diels-Alder reaction of propenenitriles with enol ethers: A convenient approach to functionalized 3,4-dihydro-2H-pyrans
Palasz, Aleksandra,Bogdanowicz-Szwed, Krystyna
, p. 647 - 655 (2008)
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.
