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  • Title: Synthesis of 3,4-dihydro-2H-pyrans by hetero-Diels-Alder reactions of functionalized alpha,beta-unsaturated carbonyl compounds with N-vinyl-2-oxazolidinone.
    Author: Pałasz A.
    Journal: Org Biomol Chem; 2005 Sep 07; 3(17):3207-12. PubMed ID: 16106303.
    Abstract:
    Cycloadditions of 3-aryl-2-benzoyl-2-propenenitriles and 3-phenylsulfonyl-3-buten-2-one to N-vinyl-2-oxazolidinone proceed regio- and diastereoselectively yielding cis and trans diastereoisomers of 4-aryl-3,4-dihydro-2-(2-oxo-3-oxazolidinyl)-2H-pyrans in 37-65% yield. Cycloadducts cis- were the major products. Reaction of 5-arylidene-1,3-dimethylbarbituric acids with dienophile afforded mixtures of 2H-pyrano[2,3-d]pyrimidine-2,4(3H)-diones trans and products resulted from an elimination of 2-oxazolidinone, in 50-52% yield. To confirm the experimental results, semiempirical AM1 and PM3 calculations of frontier orbital energies have been performed.
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