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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...
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/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. |
format | Online Article Text |
id | pubmed-6514811 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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