Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach

(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140–250 °C. We find that the use of tri-n-butylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60–70 °C). Several coumarins were pr...

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Autores principales: Boeck, Florian, Blazejak, Max, Anneser, Markus R, Hintermann, Lukas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3510995/
https://www.ncbi.nlm.nih.gov/pubmed/23209495
http://dx.doi.org/10.3762/bjoc.8.186
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author Boeck, Florian
Blazejak, Max
Anneser, Markus R
Hintermann, Lukas
author_facet Boeck, Florian
Blazejak, Max
Anneser, Markus R
Hintermann, Lukas
author_sort Boeck, Florian
collection PubMed
description (E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140–250 °C. We find that the use of tri-n-butylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60–70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph(3)P=CHCO(2)Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.
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spelling pubmed-35109952012-12-03 Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach Boeck, Florian Blazejak, Max Anneser, Markus R Hintermann, Lukas Beilstein J Org Chem Full Research Paper (E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140–250 °C. We find that the use of tri-n-butylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60–70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph(3)P=CHCO(2)Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization. Beilstein-Institut 2012-09-26 /pmc/articles/PMC3510995/ /pubmed/23209495 http://dx.doi.org/10.3762/bjoc.8.186 Text en Copyright © 2012, Boeck 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
Boeck, Florian
Blazejak, Max
Anneser, Markus R
Hintermann, Lukas
Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
title Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
title_full Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
title_fullStr Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
title_full_unstemmed Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
title_short Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
title_sort cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: a nucleophilic organocatalysis approach
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3510995/
https://www.ncbi.nlm.nih.gov/pubmed/23209495
http://dx.doi.org/10.3762/bjoc.8.186
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