Microwave-assisted Kabachnik-Fields reaction with amino alcohols as the amine component

Tajti, Ádám (author), Szatmári, Enikő (author), Perdih, Franc (author), Keglevich, G. (author), Bálint, Erika (author)

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.

• Language: English
• Keywords: α-aminophosphonate derivatives, Kabachnik-Fields reaction, amino alcohols, microwave, X-ray diffraction
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2019
• Number of pages: 13 str.
• Numbering: Vol. 24, iss. 8, art. 1640
• PID: 20.500.12556/RUL-132249
• UDC: 547.435-732
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules24081640
• COBISS.SI-ID: 1538222531
• Publication date in RUL: 19.10.2021

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 25.04.2019

Secondary language

• Language: Slovenian
• Keywords: aminofosfonati, Kabachnik-Fieldsova reakcija, amino alkoholi, mikrovalovi, rentgenska difrakcija