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Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component

In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyeth...

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Autores principales: Tajti, Ádám, Szatmári, Enikő, Perdih, Franc, Keglevich, György, Bálint, Erika
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6514811/
https://www.ncbi.nlm.nih.gov/pubmed/31027303
http://dx.doi.org/10.3390/molecules24081640
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author Tajti, Ádám
Szatmári, Enikő
Perdih, Franc
Keglevich, György
Bálint, Erika
author_facet Tajti, Ádám
Szatmári, Enikő
Perdih, Franc
Keglevich, György
Bálint, Erika
author_sort Tajti, Ádám
collection PubMed
description In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,N-Bis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik–Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.
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spelling pubmed-65148112019-05-30 Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component Tajti, Ádám Szatmári, Enikő Perdih, Franc Keglevich, György Bálint, Erika Molecules Article In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,N-Bis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik–Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis. MDPI 2019-04-25 /pmc/articles/PMC6514811/ /pubmed/31027303 http://dx.doi.org/10.3390/molecules24081640 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
Tajti, Ádám
Szatmári, Enikő
Perdih, Franc
Keglevich, György
Bálint, Erika
Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
title Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
title_full Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
title_fullStr Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
title_full_unstemmed Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
title_short Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
title_sort microwave-assisted kabachnik–fields reaction with amino alcohols as the amine component
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6514811/
https://www.ncbi.nlm.nih.gov/pubmed/31027303
http://dx.doi.org/10.3390/molecules24081640
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