Synthesis of derivatives of 4-alkylthiouracil, cytosine, pyrido[2,3-d]pyrimidine, and pyrimido[4,5-d]pyrimidine from the N,S- and N,N-acetals of diacetylketene and isocyanates

  • V. A. Dorokhov
  • M. F. Gordeev
  • A. V. Komkov
  • V. S. Bogdanov
Organic Chemistry

Abstract

The action of alkyl and aryl isocyanates on the N,S-acetals of diacetylketene leads to the formation of 4-alkylthio-5-acetyl-1-alkyl(aryl)-6-methyl-1H-pyrimidin-2-ones (derivatives of 4-alkylthiouracils). The reaction of the synthesized thiouracils with amines or the reaction of the N,N-acetals of diacetylketene (N,N-ADK) with an equi-molar amount of aryl isocyanates leads to the formation of substituted 4-amino-5-acetyl-1H-pyrimidin-2-ones (derivatives of cytosine). From the latter and isocyanates or directly from N,N-ADK and an excess of the isocyanate, derivatives of 4-methylene-1H,3H, 4H-pyrimido[4,5-d]pyrimidine-2,7-dione were obtained. The exception was the condensation of 3-[N-(4,6-dimethyl-2-pyrimidinyl)diaminomethylene]pentane-2,4-dione with aryl isocyanates, which led to 3H,8H-pyrido[2,3-d]pyrimidine-2,5-diones.

Keywords

Pyrimidine Cytosine Dione Isocyanate Thiouracil 

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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • V. A. Dorokhov
    • 1
  • M. F. Gordeev
    • 1
  • A. V. Komkov
    • 1
  • V. S. Bogdanov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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