Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone

From the treatment of 5-hydroxy-1,4-naphthoquinone (juglone) with acetic anhydride and H(2)SO(4) followed subsequently by treatment with methanolic HCl, 5-hydroxy-3-methoxy-1,4-naphthoquinone (3-methoxy juglone) and 8-hydroxy-4-methoxy-1,2-naphthoquinone were obtained as products rather than the ant...

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Detalles Bibliográficos
Autores principales: Blauenburg, Bastian, Metsä-Ketelä, Mikko, Klika, Karel D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Scholarly Research Network 2012
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3767210/
https://www.ncbi.nlm.nih.gov/pubmed/24052839
http://dx.doi.org/10.5402/2012/274980
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author Blauenburg, Bastian
Metsä-Ketelä, Mikko
Klika, Karel D.
author_facet Blauenburg, Bastian
Metsä-Ketelä, Mikko
Klika, Karel D.
author_sort Blauenburg, Bastian
collection PubMed
description From the treatment of 5-hydroxy-1,4-naphthoquinone (juglone) with acetic anhydride and H(2)SO(4) followed subsequently by treatment with methanolic HCl, 5-hydroxy-3-methoxy-1,4-naphthoquinone (3-methoxy juglone) and 8-hydroxy-4-methoxy-1,2-naphthoquinone were obtained as products rather than the anticipated product 2,5-dihydroxy-1,4-naphthoquinone (2-hydroxy juglone). The reaction and the identification of the products are discussed in terms of NMR and DFT calculations.
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spelling pubmed-37672102013-09-19 Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone Blauenburg, Bastian Metsä-Ketelä, Mikko Klika, Karel D. ISRN Org Chem Research Article From the treatment of 5-hydroxy-1,4-naphthoquinone (juglone) with acetic anhydride and H(2)SO(4) followed subsequently by treatment with methanolic HCl, 5-hydroxy-3-methoxy-1,4-naphthoquinone (3-methoxy juglone) and 8-hydroxy-4-methoxy-1,2-naphthoquinone were obtained as products rather than the anticipated product 2,5-dihydroxy-1,4-naphthoquinone (2-hydroxy juglone). The reaction and the identification of the products are discussed in terms of NMR and DFT calculations. International Scholarly Research Network 2012-09-23 /pmc/articles/PMC3767210/ /pubmed/24052839 http://dx.doi.org/10.5402/2012/274980 Text en Copyright © 2012 Bastian Blauenburg et al. https://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Blauenburg, Bastian
Metsä-Ketelä, Mikko
Klika, Karel D.
Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
title Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
title_full Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
title_fullStr Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
title_full_unstemmed Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
title_short Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone
title_sort formation of 5-hydroxy-3-methoxy-1,4-naphthoquinone and 8-hydroxy-4-methoxy-1,2-naphthoquinone from juglone
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3767210/
https://www.ncbi.nlm.nih.gov/pubmed/24052839
http://dx.doi.org/10.5402/2012/274980
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