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Russian Journal of General Chemistry

, Volume 88, Issue 10, pp 2072–2078 | Cite as

Synthesis of Isomeric Aminomethyl Derivatives of Furylmethanephosphonates

  • L. M. PevznerEmail author
Article
  • 11 Downloads

Abstract

By chloromethylation of diethyl 2- and 3-furylmethanephosphonates 5-chloromethylfur-2(3)-ylmethanephosphonates were synthesized. The other four isomers of chloromethyl derivatives of furylmethanephosphonates were prepared by substitution of hydroxy groups in the corresponding phosphorylated furylmethanols via the reaction with thionyl chloride in the presence of pyridine. Thermal stability of these chlorides was sufficiently high, and they were involved in nucleophilic substitution of chlorine with azido group by treating with sodium azide in boiling acetonitrile in the presence of potassium iodide. No decomposition of substrates was observed. The azides obtained were reduced to amines with triphenylphosphine in ethanol.

Keywords

azidomethylfurans reduction with triphenylphosphine aminophosphonates furylmethanephosphonates 

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References

  1. 1.
    Pevzner, L.M., Russ. J. Gen. Chem., 2017, vol. 87, no. 11, p. 2563. doi 10.1134/S1070363217110093CrossRefGoogle Scholar
  2. 2.
    Pevzner, L.M. and Zavgorodnii, V.S., Russ. J. Gen. Chem., 2018, vol. 88, no. 3, p. 439. doi 10.1134/S1070363218030106CrossRefGoogle Scholar
  3. 3.
    www.pharmaexpert.ru/passonline.Google Scholar
  4. 4.
    Pevzner, L.M., Russ. J. Gen. Chem., 2008, vol. 78, no. 2, p. 206. doi 10.1134/S1070363208020096CrossRefGoogle Scholar
  5. 5.
    Pevzner, L.M., Russ. J. Gen. Chem., 2011, vol. 81, no. 8, p. 1620. doi 10.1134/S107036321108007XCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.St. Petersburg State Institute of Technology (Technical University)St. PetersburgRussia

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