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New method for the synthesis of amino-phosphonic acids. Communication 2. Reaction of ketones with dialkyl phosphites and ammonia

  • Organic and Biological Chemistry
  • Published:
Image Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    It has been shown that our condensation reaction between dialkyl phosphites, aldehydes, and ammonia can be extended also to ketones. The reaction can be applied not only to aliphatic and alicyclic ketones, but also to aliphatic-aromatic and purely aromatic ketones. The reaction of dialkyl phosphites with ammonia and ketones results in the formation of esters of a-amino phosphoric acids having a branched radical.

  2. 2.

    A simple method has been developed for the preparation of amino phosphoric acids by the action of ketones on dialkyl phosphites and ammonia, and hydrolysis of the esters so formed.

  3. 3.

    The following substances have been synthesized and characterized: 1-amino-1-methylethylphosphonic acid, 1-amino-1-methylpropylphosphonic acid, 1-amino-1-methylbuiylphospbdnic acid. 1-amino-1-propylbutylphosphonic acid; 1-aminocyclohexylphosphonic acid. 1-amino-1-phenylethylphosphonic acid. and aminodiphenyl methylphosphonic acid. add also their esters, and the hydrochlorides and picrates of these esters.

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Literature cited

  1. M. I. Kabachnik and T. Ya. Medved, Bull. Acad. Sci. USSR Div. Chem. Sci., 1953, 5, 868.

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  2. V. S. Abramov, J. Gen. Chem., 22, 647 (1952).

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  3. J. B. Conant, B. B. Coyne, J. Am. Chem. Soc., 44, 2630 (1922).

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Medved, T.Y., Kabachnik, M.I. New method for the synthesis of amino-phosphonic acids. Communication 2. Reaction of ketones with dialkyl phosphites and ammonia. Russ Chem Bull 3, 255–261 (1954). https://doi.org/10.1007/BF01177621

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  • DOI: https://doi.org/10.1007/BF01177621

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