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The Synthesis of Bis(α-aryl-methylphosphonoyl)amines by the Microwave-Assisted Catalyst-Free Tandem Kabachnik–Fields Reaction

Year: 2026

Type: article

Abstract: Potentially biologically active α-aminophosphonic derivatives were prepared by the Kabachnik–Fields condensation of α-amino-α-aryl-methylphosphonates, arylaldehydes, and diethyl phosphite to afford bis(α-aryl-methylphosphonoyl)-amines as a mixture of racemic and meso isomers. To go “green”—performing the transformations under microwave irradiation—there was no need for a catalyst. On the other hand, the phospha-Mannich reaction of α-amino-α-phenyl-methylphosphonate with arylaldehydes led to (α-aryl-methylphosphonoyl)-(α-phenyl-methylphosphonoyl)-amines as a mixture of SS/RR and SR/RS racemates. Moreover, the respective symmetric products with identical aryl groups were also present. The outcome was similar, when α-amino-α-aryl-methyl-phosphonates were condensed with benzaldehyde and diethyl phosphite. The products were analyzed by 1D and 2D NMR spectroscopy. The combined NMR analysis of the products confirmed their structure.

Source: Catalysts

DOI: 10.3390/catal16020148

Authors: Bence Bajusz, Konstantin Karaghiosoff, László Drahos, Ágnes Gömöry, György Keglevich

Institutions: Budapest University of Technology and Economics, Ludwig-Maximilians-Universität München, HUN-REN Research Centre for Natural Sciences

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,654

Funders: European Commission, National Research, Development and Innovation Office