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-<i>H</i>-phosphinate, and secondary phosphine oxides) is reported...

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Main Authors:	Ádám Tajti, Enikő Szatmári, Franc Perdih, György Keglevich, Erika Bálint
Format:	Article
Language:	English
Published:	MDPI AG 2019-04-01
Series:	Molecules
Subjects:	α-aminophosphonate derivatives Kabachnik–Fields reaction amino alcohols microwave X-ray diffraction
Online Access:	https://www.mdpi.com/1420-3049/24/8/1640

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spelling	doaj-d956a2d6019a4766aaf4072fc558b2952020-11-25T00:09:22ZengMDPI AGMolecules1420-30492019-04-01248164010.3390/molecules24081640molecules24081640Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine ComponentÁdám Tajti0Enikő Szatmári1Franc Perdih2György Keglevich3Erika Bálint4Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryFaculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000 Ljubljana, SloveniaDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, HungaryIn 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-<i>H</i>-phosphinate, and secondary phosphine oxides) is reported. The synthesis of <i>N</i>-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. <i>N</i>,<i>N</i>-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.https://www.mdpi.com/1420-3049/24/8/1640α-aminophosphonate derivativesKabachnik–Fields reactionamino alcoholsmicrowaveX-ray diffraction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Ádám Tajti Enikő Szatmári Franc Perdih György Keglevich Erika Bálint
spellingShingle	Ádám Tajti Enikő Szatmári Franc Perdih György Keglevich Erika Bálint Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component Molecules α-aminophosphonate derivatives Kabachnik–Fields reaction amino alcohols microwave X-ray diffraction
author_facet	Ádám Tajti Enikő Szatmári Franc Perdih György Keglevich Erika Bálint
author_sort	Ádám Tajti
title	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_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_sort	microwave-assisted kabachnik–fields reaction with amino alcohols as the amine component
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2019-04-01
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-<i>H</i>-phosphinate, and secondary phosphine oxides) is reported. The synthesis of <i>N</i>-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. <i>N</i>,<i>N</i>-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.
topic	α-aminophosphonate derivatives Kabachnik–Fields reaction amino alcohols microwave X-ray diffraction
url	https://www.mdpi.com/1420-3049/24/8/1640
work_keys_str_mv	AT adamtajti microwaveassistedkabachnikfieldsreactionwithaminoalcoholsastheaminecomponent AT enikoszatmari microwaveassistedkabachnikfieldsreactionwithaminoalcoholsastheaminecomponent AT francperdih microwaveassistedkabachnikfieldsreactionwithaminoalcoholsastheaminecomponent AT gyorgykeglevich microwaveassistedkabachnikfieldsreactionwithaminoalcoholsastheaminecomponent AT erikabalint microwaveassistedkabachnikfieldsreactionwithaminoalcoholsastheaminecomponent
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Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component

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