Synthesis of 1-(aryloxyalkyl)- 5-(arylamino)uracils

Authors

  • А. А. Озеров Pharmacology Scientific Research Institute, Volgograd Medical Academy, Volgograd 400066
  • М. C. Новиков Pharmacology Scientific Research Institute, Volgograd Medical Academy, Volgograd 400066
  • А. K. Брель Pharmacology Scientific Research Institute, Volgograd Medical Academy, Volgograd 400066
  • Г. H. Солодунова Pharmacology Scientific Research Institute, Volgograd Medical Academy, Volgograd 400066

Abstract

In an attempt to obtain new non-nucleoside inhibitors of the reverse transcriptase HIV-1, we have carried out the synthesis of 1-(benzyloxymethyl)- and 1-[2-(4-R-phenoxy)ethyl]-5-(arylamino)uracils. Indirect alkylation of trimethylsilyl derivatives of 5-(arylamino)uracils with benzyl chloromethyl ether by the Gilbert-Jones method did not affect the exocyclic amino group and gave the corresponding 1-(benzyloxymethyl) derivatives in 58–74% yield. Alkylation of 5-(arylamino)uracils with 1-bromo-2-(4-R-phenoxy)ethane in anhydrous DMF in the presence of potassium carbonate gave a mixture of N1-mono- and N1,N1-disubstituted products with an overall yield of 46–55%.

How to Cite
Ozerov, A. A.; Novikov, M. S.; Brel', A. K.; Solodunova, G. N. Chem. Heterocycl. Compd. 1998, 34, 611. [Khim. Geterotsikl. Soedin. 1998, 34, 691.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02290947

Published

1998-05-25

Issue

Section

Original Papers