Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

A number of N-phenyl-1,4-naphthoquinone monoimines 6–10 were prepared by on-water oxidative phenylamination of 1,5-dihydroxynaphthalene (1) and 5-acetylamino-1-hydroxynaphthalene (5) with oxygen-substituted phenylamines under aerobic conditions and either solar or green LED radiation, in the presenc...

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Detalles Bibliográficos
Autores principales: Benites, Julio, Meléndez, Juan, Estela, Cynthia, Ríos, David, Espinoza, Luis, Brito, Iván, Valderrama, Jaime A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222432/
https://www.ncbi.nlm.nih.gov/pubmed/25383115
http://dx.doi.org/10.3762/bjoc.10.255
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author Benites, Julio
Meléndez, Juan
Estela, Cynthia
Ríos, David
Espinoza, Luis
Brito, Iván
Valderrama, Jaime A
author_facet Benites, Julio
Meléndez, Juan
Estela, Cynthia
Ríos, David
Espinoza, Luis
Brito, Iván
Valderrama, Jaime A
author_sort Benites, Julio
collection PubMed
description A number of N-phenyl-1,4-naphthoquinone monoimines 6–10 were prepared by on-water oxidative phenylamination of 1,5-dihydroxynaphthalene (1) and 5-acetylamino-1-hydroxynaphthalene (5) with oxygen-substituted phenylamines under aerobic conditions and either solar or green LED radiation, in the presence of rose bengal as singlet oxygen sensitizer. As compared to the conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions “on water” instead of hazardous oxidant reagents currently employed in aqueous alcoholic media.
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spelling pubmed-42224322014-11-07 Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water” Benites, Julio Meléndez, Juan Estela, Cynthia Ríos, David Espinoza, Luis Brito, Iván Valderrama, Jaime A Beilstein J Org Chem Letter A number of N-phenyl-1,4-naphthoquinone monoimines 6–10 were prepared by on-water oxidative phenylamination of 1,5-dihydroxynaphthalene (1) and 5-acetylamino-1-hydroxynaphthalene (5) with oxygen-substituted phenylamines under aerobic conditions and either solar or green LED radiation, in the presence of rose bengal as singlet oxygen sensitizer. As compared to the conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions “on water” instead of hazardous oxidant reagents currently employed in aqueous alcoholic media. Beilstein-Institut 2014-10-22 /pmc/articles/PMC4222432/ /pubmed/25383115 http://dx.doi.org/10.3762/bjoc.10.255 Text en Copyright © 2014, Benites 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
Benites, Julio
Meléndez, Juan
Estela, Cynthia
Ríos, David
Espinoza, Luis
Brito, Iván
Valderrama, Jaime A
Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
title Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
title_full Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
title_fullStr Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
title_full_unstemmed Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
title_short Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
title_sort oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to n-phenyl-1,4-naphthoquinone monoimines by air and light “on water”
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222432/
https://www.ncbi.nlm.nih.gov/pubmed/25383115
http://dx.doi.org/10.3762/bjoc.10.255
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