DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone

The carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone with carbon dioxide promoted by the organic base 1,8-diazabicycloundec-7-ene (DBU) is reported. This reaction provides convenient access to the biologically important compounds 4-hydroxy-2H-chromen-2-one and 4-hydroxy-2(1H)-quin...

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Detalles Bibliográficos
Autores principales: Zhang, Wen-Zhen, Liu, Si, Lu, Xiao-Bing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464362/
https://www.ncbi.nlm.nih.gov/pubmed/26124893
http://dx.doi.org/10.3762/bjoc.11.102
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author Zhang, Wen-Zhen
Liu, Si
Lu, Xiao-Bing
author_facet Zhang, Wen-Zhen
Liu, Si
Lu, Xiao-Bing
author_sort Zhang, Wen-Zhen
collection PubMed
description The carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone with carbon dioxide promoted by the organic base 1,8-diazabicycloundec-7-ene (DBU) is reported. This reaction provides convenient access to the biologically important compounds 4-hydroxy-2H-chromen-2-one and 4-hydroxy-2(1H)-quinolinone in moderate to good yields using carbon dioxide as the carboxylation reagent. An acyl migration from nitrogen to carbon is observed in the reaction of o-acetamidoacetophenone.
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spelling pubmed-44643622015-06-29 DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone Zhang, Wen-Zhen Liu, Si Lu, Xiao-Bing Beilstein J Org Chem Letter The carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone with carbon dioxide promoted by the organic base 1,8-diazabicycloundec-7-ene (DBU) is reported. This reaction provides convenient access to the biologically important compounds 4-hydroxy-2H-chromen-2-one and 4-hydroxy-2(1H)-quinolinone in moderate to good yields using carbon dioxide as the carboxylation reagent. An acyl migration from nitrogen to carbon is observed in the reaction of o-acetamidoacetophenone. Beilstein-Institut 2015-05-29 /pmc/articles/PMC4464362/ /pubmed/26124893 http://dx.doi.org/10.3762/bjoc.11.102 Text en Copyright © 2015, Zhang 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 Letter
Zhang, Wen-Zhen
Liu, Si
Lu, Xiao-Bing
DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
title DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
title_full DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
title_fullStr DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
title_full_unstemmed DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
title_short DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
title_sort dbu-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464362/
https://www.ncbi.nlm.nih.gov/pubmed/26124893
http://dx.doi.org/10.3762/bjoc.11.102
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