A Five-Component Biginelli-Diels-Alder Cascade Reaction

Frontiers in Chemistry
Taber S MaskreyPeter Wipf

Abstract

A new multi-component condensation was discovered during the reaction of a urea, β-keto ester, and formaldehyde. In the presence of catalytic indium bromide, a Biginelli dihydropyrimidinone intermediate was further converted to a five-component condensation product through a formal hetero Diels-Alder reaction. The product structure was confirmed by NMR and NOE analysis, and the proposed stepwise mechanism was supported by the reaction of the Biginelli intermediate with ethyl 2-methylene-3-oxobutanoate.

References

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Citations

Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Giovanna BosicaNicole Mariotti

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Methods Mentioned

BETA
NMR
PMA

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