Chemistry of Heterocyclic Compounds

, Volume 18, Issue 2, pp 202–205 | Cite as

Analogs of pyrimidine nucleosides. 17. Synthesis of 1-[5(2)-fluoromethyltetrahydro-2-furyl]uracils

  • L. T. Kaulinya
  • L. M. Yagupol'skii
  • N. V. Kondratenko
  • E. P. Vechirko
  • A. É. Berzlnya
  • V. N. Silinya
  • É. É. Liepin'sh
  • M. Yu. Lidak
  • R. A. Zhuk
Article
  • 37 Downloads

Abstract

The synthesis of 2-fluoromethyltetrahydrofuran is described, and it is shown that chlorination of the latter gives 2-chloro-5- and 2-chloro-2-fluoromethyltetrahydrofurans in a ratio of 5:1. 2,4-Bis(trimethylsilyl) derivatives of uracil were alkylated by means of the mixture of α-chloro ethers without separation, and a mixture of the cis and trans isomers of 1-(5-fluoromethyltetrahydro-2-furyl)uracils and 1-(2-fluoromethyltetrahydro-2-furyl)uracils were obtained. The reaction products were identified on the basis of the PMR spectra.

Keywords

Ether Organic Chemistry Pyrimidine Nucleoside Uracil 

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Literature cited

  1. 1.
    L. T. Kaulinya, É. É. Liepin'sh, M. Yu. Lidak, and R. A. Zhuk, Khim. Geterotsikl. Soedin., No. 1, 101 (1982).Google Scholar
  2. 2.
    G. Barger, R. Robinson, and L. H. Smith, J. Chem. Soc., 718 (1937).Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • L. T. Kaulinya
    • 1
    • 2
  • L. M. Yagupol'skii
    • 1
    • 2
  • N. V. Kondratenko
    • 1
    • 2
  • E. P. Vechirko
    • 1
    • 2
  • A. É. Berzlnya
    • 1
    • 2
  • V. N. Silinya
    • 1
    • 2
  • É. É. Liepin'sh
    • 1
    • 2
  • M. Yu. Lidak
    • 1
    • 2
  • R. A. Zhuk
    • 1
    • 2
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga
  2. 2.Institute of Organic ChemistryAcademy of Sciences of the Ukrainian SSRKiev

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