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Synthesis and Reactions of α-Hydroxyphosphonates
This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphon...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099812/ https://www.ncbi.nlm.nih.gov/pubmed/29925805 http://dx.doi.org/10.3390/molecules23061493 |
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author | Rádai, Zita Keglevich, György |
author_facet | Rádai, Zita Keglevich, György |
author_sort | Rádai, Zita |
collection | PubMed |
description | This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids. |
format | Online Article Text |
id | pubmed-6099812 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-60998122018-11-13 Synthesis and Reactions of α-Hydroxyphosphonates Rádai, Zita Keglevich, György Molecules Review This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids. MDPI 2018-06-20 /pmc/articles/PMC6099812/ /pubmed/29925805 http://dx.doi.org/10.3390/molecules23061493 Text en © 2018 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 | Review Rádai, Zita Keglevich, György Synthesis and Reactions of α-Hydroxyphosphonates |
title | Synthesis and Reactions of α-Hydroxyphosphonates |
title_full | Synthesis and Reactions of α-Hydroxyphosphonates |
title_fullStr | Synthesis and Reactions of α-Hydroxyphosphonates |
title_full_unstemmed | Synthesis and Reactions of α-Hydroxyphosphonates |
title_short | Synthesis and Reactions of α-Hydroxyphosphonates |
title_sort | synthesis and reactions of α-hydroxyphosphonates |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099812/ https://www.ncbi.nlm.nih.gov/pubmed/29925805 http://dx.doi.org/10.3390/molecules23061493 |
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