A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones

A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition–palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted...

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Autores principales: John, Jubi, Târcoveanu, Eliza, Jones, Peter G, Hopf, Henning
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077403/
https://www.ncbi.nlm.nih.gov/pubmed/24991301
http://dx.doi.org/10.3762/bjoc.10.150
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author John, Jubi
Târcoveanu, Eliza
Jones, Peter G
Hopf, Henning
author_facet John, Jubi
Târcoveanu, Eliza
Jones, Peter G
Hopf, Henning
author_sort John, Jubi
collection PubMed
description A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition–palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted furanones in good to excellent yields. 4-Hydrazino-3(2H)-furanones could also be synthesized from diazo esters in excellent yields by utilising the developed strategy. We could also efficiently transform the substituted furanones to aza-prostaglandin analogues.
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spelling pubmed-40774032014-07-02 A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones John, Jubi Târcoveanu, Eliza Jones, Peter G Hopf, Henning Beilstein J Org Chem Full Research Paper A facile route towards highly functionalized 3(2H)-furanones via a sequential Mannich addition–palladium catalyzed ring closing has been elaborated. The reaction of 4-chloroacetoacetate esters with imines derived from aliphatic and aromatic aldehydes under palladium catalysis afforded 4-substituted furanones in good to excellent yields. 4-Hydrazino-3(2H)-furanones could also be synthesized from diazo esters in excellent yields by utilising the developed strategy. We could also efficiently transform the substituted furanones to aza-prostaglandin analogues. Beilstein-Institut 2014-06-27 /pmc/articles/PMC4077403/ /pubmed/24991301 http://dx.doi.org/10.3762/bjoc.10.150 Text en Copyright © 2014, John et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
John, Jubi
Târcoveanu, Eliza
Jones, Peter G
Hopf, Henning
A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones
title A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones
title_full A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones
title_fullStr A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones
title_full_unstemmed A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones
title_short A tandem Mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones
title_sort tandem mannich addition–palladium catalyzed ring-closing route toward 4-substituted-3(2h)-furanones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077403/
https://www.ncbi.nlm.nih.gov/pubmed/24991301
http://dx.doi.org/10.3762/bjoc.10.150
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