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. 2019 Apr 25;24(8):1640.
doi: 10.3390/molecules24081640.

Microwave-Assisted Kabachnik⁻Fields Reaction With Amino Alcohols as the Amine Component

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Free PMC article

Microwave-Assisted Kabachnik⁻Fields Reaction With Amino Alcohols as the Amine Component

Ádám Tajti et al. Molecules. .
Free PMC article

Abstract

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.

Keywords: Kabachnik–Fields reaction; X-ray diffraction; amino alcohols; microwave; α-aminophosphonate derivatives.

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Condensation of ethanolamine, paraformaldehyde, and diethyl phosphite.
Figure 1
Figure 1
X-ray structures and atom numbering of compounds 11a and 12a∙H2O. Probability ellipsoids are drawn at the 30% level.

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