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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6359518 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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