Chemistry of Heterocyclic Compounds

, Volume 28, Issue 12, pp 1432–1438 | Cite as

Synthesis of derivatives of new heterocyclic system 5,7-dioxo(4h,6h)-1,3-dithiolo[4,5-d]pyrimidine on the basis of barbituric acid

  • O. Ya. Neiland
  • V. Yu. Khodorkovskii
  • V. Zh. Tilika
Article

Abstract

The 5-phenyliodonium betaine of barbituric acid reacts with sodium diethyldithiocarbamate to form 5-(diethylaminothiocarbonylthio)barbituric acid, which is cyclized in concentrated H2SO4 solution to form the cation of 5,7-dioxo(4H,6H)-1,3-dithiolo[4,5-d]pyrimidine, isolated in the form of the perchlorate and the chloride. These salts are split by sodium sulflde or selenide, forming 5-[diethylaminothio (seleno)carbonylthio]-4-thiobarbituric acids, which are cyclized by the action of concentrated HCl in an organic solvent to form 5,7-dioxo(4H,6H)-1,3-dithiolo[4,5-d]pyrimidinethione (selenone)-2. The thione and the selenone, as NH acids, form salts; alkylation of the tetrabutylammonium salt affords N(4)-alkyl and N,N′-dialkyl derivatives. The compounds that were obtained have been characterized by IR and PMR spectra.

Keywords

Pyrimidine Perchlorate Betaine Thiobarbituric Acid Selenide 

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References

  1. 1.
    V. Yu. Khodorkovskii and O. Ya. Neiland, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 2, 131 (1982).Google Scholar
  2. 2.
    A. Krief, Tetrahedron, 42, 1209 (1986).Google Scholar
  3. 3.
    O. Ya. Neiland and B. Ya. Adamsone, Khim. Geterotsikl. Soedin., No. 6, 848 (1991).Google Scholar
  4. 4.
    O. Ya. Neiland and D. é. Neiman, Zh. Org. Khim., 6, 2509 (1970).Google Scholar
  5. 5.
    V. I. Slesarev and B. A. Ivin, Zh. Org. Khim., 10, 114 (1974).Google Scholar
  6. 6.
    C. L. Angel, J. Chem. Soc., No. 2, 504 (1961).Google Scholar
  7. 7.
    O. Ya. Neiland and N. N. Zagorskaya, Khim. Geterotsikl. Soedin., No. 3, 416 (1992).Google Scholar
  8. 8.
    V. Zh. Tilika, V. Yu. Khodorkovskii, and O. Ya. Neiland, USSR Inventor's Certificate 1,738,810.Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • O. Ya. Neiland
    • 1
  • V. Yu. Khodorkovskii
    • 1
  • V. Zh. Tilika
    • 1
  1. 1.Riga Technical UniversityRiga

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