A Five-Component Biginelli-Diels-Alder Cascade Reaction

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-Alde...

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Detalles Bibliográficos
Autores principales: Maskrey, Taber S., Frischling, Madeline C., Rice, Mikhaila L., Wipf, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6119773/
https://www.ncbi.nlm.nih.gov/pubmed/30211156
http://dx.doi.org/10.3389/fchem.2018.00376
Descripción
Sumario: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.

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