Phosphonomethylated derivatives of dinitroanilines

A. L. Chuiko, Yu. V. Korotkiy, V. A. Bondar


A number of dinitroanilines derivatives previously unknown has been synthesized. The alkylamino groups and aminomethylphosphonic groups have been introduced as acids and esters in their structure. The synthesis has been carried out by Kabachnik-Fields reaction and its modification – Moedritzer-Irani reaction, in which formaldehyde and phosphonic acids are used in a highly acidic medium. However, we have not found any other examples of successful application of this reaction to aniline derivatives in the literature. Thus, the possibility to use Moedritzer-Irani reaction to dinitrosubstituted anilines has been found. Obviously, the fact that two nitrogroups reactivate the aromatic ring of aniline is enough to fully avoid adverse polymerization associated with the interaction of formaldehyde with the benzene ring in this case. This polymerization makes it impossible to use Moedritzer-Irani reaction for other compounds with the aniline moiety. Benzylaminophosphonic acids esters have been also synthesized based on dialkyl phosphites and Schiff bases using Kabachnik-Fields reaction with subsequent hydrolyzation to the acids. The required aminosubstituted dinitroanilines with aliphatic aminogroups have been synthesized by the reaction of aliphatic diamines with dinitrochlorbenzenes. The structure of the compounds  obtained has been confirmed by the methods of 1H and 31P NMR spectroscopy and elemental analysis. As a result, the application of Moedritzer-Irani reaction has been expanded, and due to it aminomethylphosphonic acids that are previously unknown and structurally similar to the known herbicides have been synthesized.


a-aminophosphonates; dinitroanilines; Kabachnik-Fields reaction; Moedritzer-Irani reaction


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