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Russian Journal of General Chemistry

, Volume 86, Issue 12, pp 2616–2623 | Cite as

5-Trifluoromethylfuryl derivatives of phosphocarboxylic acids

  • E. P. Doronina
  • L. M. PevznerEmail author
  • V. A. Polukeev
  • M. L. Petrov
Article

Abstract

Methods of synthesis of trifluoromethylfuryl derivatives of phosphonocarboxylic acids are studied. By addition of diethyl hydrogen phosphite to alkyl 3-(5-trifluoromethylfur-2-yl)acrylate under the conditions of the Pudovik reaction the corresponding derivative of 3-phosphonopropionic acid was prepared. Diethyl (5-trifluoromethylfur-2-yl)methanephosphonate in presence of potassium tert-butylate reacts with ethyl acrylate to form trifluoromethylfuryl derivative of 4-phosphonobutyric or 4-phosphonopimelic acid depending on the reaction conditions. In the products of reaction of the alkyl 3-(5-trifluoromethylfur-2-yl)-3-(diethoxyphosphoryl) propionate with ethyl acrylate in the presence of potassium tert-butylate formation of trifluoromethylfuryl derivative of the 3-phosphonoadipic acid is detected. 3-(5-Trifluoromethylfur-2-yl)-3-(diethoxyphosphoryl) propionic acid and its acid chloride are synthesized. The latter compound is used for acylation of glycine to form the corresponding N-acyl derivative. It is suggested that such compounds may be transported in the cell using usual channels of transportation of the amino acids and short peptides.

Keywords

trifluoromethylfurans phosphonocarboxylic acids Pudovik reaction Michael reaction acrylates acylglycine 

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Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • E. P. Doronina
    • 1
  • L. M. Pevzner
    • 1
    Email author
  • V. A. Polukeev
    • 2
  • M. L. Petrov
    • 1
  1. 1.St. Petersburg State Institute of Technology (Technical University)St. PetersburgRussia
  2. 2.Institute of Experimental MedicineSt. PetersburgRussia

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