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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...

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Detalles Bibliográficos
Autores principales: Rádai, Zita, Keglevich, György
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
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.
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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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