Phosphonomethylated derivatives of dinitroanilines

Authors

  • A. L. Chuiko Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • Yu. V. Korotkiy Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • V. A. Bondar Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.15.839

Keywords:

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

Abstract

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.

Downloads

Download data is not yet available.

References

  1. Parka S. J., Soper O. F. Weed Science. 1977, Vol. 25 (1), pp.79-87.
  2. Britsun V. N., Yemets A. I., Lozinskii M. O., Blume Ya. B. Ukrainica Bioorganica Acta, 2009, Vol. 1, pp.16-27.
  3. Bartelsa P. G., Hiltona J. L. Pesticide Biochemistry and Physiology, 1973, Vol. 3 (4), pp.462-472.
  4. Britsun V. N., Shvartau V. V., Ozerova L. V., Lozinskii M. O. Patent UA 84947, 2008.
  5. Forlani G., Occhipinti A., Berlicki L., Dziedziola G., Wieczorek A., Kafarski P. Journal of Agricultural and Food Chemistry, 2008, Vol. 56 (9), pp.3193- 3199.
  6. Maier L. Phosphorus, Sulfur and Silicon and the Related Elements, 1991, Vol. 56 (1-4), pp.5-15.
  7. Linsker F., Evans R. L. J. Org. Chem., 1945. Vol. 10 (4), pp.283-285.
  8. Moedritzer K., Irani R. R. J. Org. Chem., 1966. Vol. 31 (5), pp.1603-1607.
  9. Fields E. K. J. Am. Chem. Soc., 1952, Vol. 74 (6), pp.1528-1531.
  10. Tennant G. Obschaja organicheskaja himija – General organic chemistry. М., 1982, Vol. 3, pp.476-547.
  11. Ordonez M., Rojas-Cabrera H., Cativiela C. Tetrahedron, 2009, Vol. 65, pp.17-49.
  12. Sergeeva T. A. Zaschita rastenii – Protection of plants, 1963, No.2. pp.42-43.

Downloads

Published

2015-06-10

How to Cite

(1)
Chuiko, A. L.; Korotkiy, Y. V.; Bondar, V. A. Phosphonomethylated Derivatives of Dinitroanilines. J. Org. Pharm. Chem. 2015, 13, 57-63.

Issue

Vol. 13 No. 2(50) (2015)

Section

Original Researches

License

Copyright (c) 2015 National University of Pharmacy

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors publishing their works in the Journal of Organic and Pharmaceutical Chemistry agree with the following terms:

1. Authors retain copyright and grant the journal the right of the first publication of the work under Creative Commons Attribution License allowing everyone to distribute and re-use the published material if proper citation of the original publication is given.

2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal’s published version of the work (e.g., post it to an institutional repository or publish it in a book) providing proper citation of the original publication.

3. Authors are permitted and encouraged to post their work online (e.g. in institutional repositories or on authors’ personal websites) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (see The Effect of Open Access).