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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 792–797 | Cite as

Synthesis of 6-[4-(allyl/phenyl)-5-thioxo-1,2,4-triazol-3-yl]pyrimidine-2,4-diones and their reaction with electrophiles

  • G. Mekuskiene
  • P. Vainilavicius
Article

Abstract

Cyclization of 1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)carbonyl-4-R-thiosemicarbazides in basic medium gave 6-(4-R-5-thioxo-1,2,4-triazol-3-yl)pyrimidine-2,4-diones (R = Allyl, Ph). Alkylation of the latter with iodomethane occurred at the sulphur atom to give the corresponding methylsulfanyl derivatives. Acetylation using acetyl chloride occurred at the N(1) atom of the triazole ring to the corresponding acetyl derivative when R = Ph but for R = Allyl the acetylation did not occur under the same conditions. In the presence of bromine in refluxing methanol the indicated allyl-substituted compound cyclizes to 6-bromomethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole. Under Mannich and bromination conditions the methylsulfanyl derivatives prepared form derivatives at the 5 position of the uracil ring: 5-methylmorpholino-(piperidino)-and 5-bromo-(4-R-5-thioxo-1,2,4-triazol-3-yl)pyrimidine-2,4-diones respectively.

Keywords

6-[4-(allyl/phenyl)-5-thioxo-1,2,4,-triazol-3-yl]pyrimidine-2,4-diones, 6-bromomethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole aminomethylation acetylation bromination methylation Mannich reaction products 

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References

  1. 1.
    D. J. Brown and W. B. Cowden, Austral. J. Chem., 36, 1469 (1983).CrossRefGoogle Scholar
  2. 2.
    D. Pancechowska-Ksepko, H. Foks, E. Landowska, M. Janowiec, and Z. Zwolska-Kwiek, Acta Pol. Pharm., 43, 116 (1986).Google Scholar
  3. 3.
    D. Pancechowska-Ksepko, H. Foks, M. Janowiec, and Z. Zwolska-Kwiek, Acta Pol. Pharm., 50, 259 (1993).Google Scholar
  4. 4.
    T. R. Belliotti, D. T. Konnor, and C. R. Costlan, WO Patent 9213884; Chem. Abstr., 118, 6990 (1993).Google Scholar
  5. 5.
    J. M. Kane, B. M. Baron, M. W. Dudley, S. M. Sorensen, M. A. Staeger, and F. P. Miller, J. Med. Chem., 33, 2772 (1990).CrossRefGoogle Scholar
  6. 6.
    J. M. Kane and F. P. Miller, US Patent 4912095; Chem. Abstr., 113, 211 (1990).Google Scholar
  7. 7.
    W. Eckhardt, E. Beriger, and H. Zondler, Eur. Patent 371925; Chem. Abstr., 113, 191385 (1990).Google Scholar
  8. 8.
    W. Eckhardt and E. Beriger, Eur. Patent 389426; Chem. Abstr., 114, 102006 (1991).Google Scholar
  9. 9.
    G. Mekuskiene, P. Gaidelis, and P. Vainilavicius, Pharmazie, 53, 94 (1998).Google Scholar
  10. 10.
    G. Mekuskiene, S. Tumkevicius, and P. Vainilavicius, J. Chem. Research (S), 213 (2002).Google Scholar
  11. 11.
    R. Yu. Savickiene, P. I. Vainilavicius, and L. L. Yasinskas, Zh. Vses. Khim. Obshch., 19, 462 (1974).Google Scholar
  12. 12.
    M. Dobosh, A. Pachuta, and J. Rekas, Acta Pol. Pharm., 50(2–3), 228 (1993).Google Scholar
  13. 13.
    P. Renukadevi and J. S. Biradar, Indian J. Heterocycl. Chem., 9, 107 (1999); Chem. Abstr., 132, 293710 (2000).Google Scholar
  14. 14.
    C. L. Angell, J. Chem. Soc., 504 (1961).Google Scholar
  15. 15.
    E. Wittenburg, Chem. Ber., 99, 2380 (1966).Google Scholar
  16. 16.
    J. W. Emsley, J. Feeney, and L. H. Sutcliffe, High Resolution Nuclear Magnetic Resonance Spectroscopy [Russian translation], Vol. 2, Mir, Moscow (1969).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • G. Mekuskiene
    • 1
  • P. Vainilavicius
    • 1
  1. 1.Vilnius UniversityVilniusLithuania

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