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Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines

A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, foll...

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Autores principales: Salgado-Escobar, Oscar, Hernández-Guadarrama, Alexis, Romero-Estudillo, Ivan, Linzaga-Elizalde, Irma
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6359518/
https://www.ncbi.nlm.nih.gov/pubmed/30650579
http://dx.doi.org/10.3390/molecules24020294
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author Salgado-Escobar, Oscar
Hernández-Guadarrama, Alexis
Romero-Estudillo, Ivan
Linzaga-Elizalde, Irma
author_facet Salgado-Escobar, Oscar
Hernández-Guadarrama, Alexis
Romero-Estudillo, Ivan
Linzaga-Elizalde, Irma
author_sort Salgado-Escobar, Oscar
collection PubMed
description A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition.
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spelling pubmed-63595182019-02-06 Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines Salgado-Escobar, Oscar Hernández-Guadarrama, Alexis Romero-Estudillo, Ivan Linzaga-Elizalde, Irma Molecules Article A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition. MDPI 2019-01-15 /pmc/articles/PMC6359518/ /pubmed/30650579 http://dx.doi.org/10.3390/molecules24020294 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Salgado-Escobar, Oscar
Hernández-Guadarrama, Alexis
Romero-Estudillo, Ivan
Linzaga-Elizalde, Irma
Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
title Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
title_full Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
title_fullStr Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
title_full_unstemmed Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
title_short Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
title_sort direct synthesis of phosphonates and α-amino-phosphonates from 1,3-benzoxazines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6359518/
https://www.ncbi.nlm.nih.gov/pubmed/30650579
http://dx.doi.org/10.3390/molecules24020294
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