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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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
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author Maskrey, Taber S.
Frischling, Madeline C.
Rice, Mikhaila L.
Wipf, Peter
author_facet Maskrey, Taber S.
Frischling, Madeline C.
Rice, Mikhaila L.
Wipf, Peter
author_sort Maskrey, Taber S.
collection PubMed
description 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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spelling pubmed-61197732018-09-12 A Five-Component Biginelli-Diels-Alder Cascade Reaction Maskrey, Taber S. Frischling, Madeline C. Rice, Mikhaila L. Wipf, Peter Front Chem Chemistry 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. Frontiers Media S.A. 2018-08-24 /pmc/articles/PMC6119773/ /pubmed/30211156 http://dx.doi.org/10.3389/fchem.2018.00376 Text en Copyright © 2018 Maskrey, Frischling, Rice and Wipf. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Maskrey, Taber S.
Frischling, Madeline C.
Rice, Mikhaila L.
Wipf, Peter
A Five-Component Biginelli-Diels-Alder Cascade Reaction
title A Five-Component Biginelli-Diels-Alder Cascade Reaction
title_full A Five-Component Biginelli-Diels-Alder Cascade Reaction
title_fullStr A Five-Component Biginelli-Diels-Alder Cascade Reaction
title_full_unstemmed A Five-Component Biginelli-Diels-Alder Cascade Reaction
title_short A Five-Component Biginelli-Diels-Alder Cascade Reaction
title_sort five-component biginelli-diels-alder cascade reaction
topic Chemistry
url 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
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