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Russian Chemical Bulletin

, Volume 62, Issue 4, pp 1060–1065 | Cite as

Heteroannulation of 6-polyfluoroalkyl-2-thiouracils

  • O. G. Khudina
  • A. E. Ivanova
  • Ya. V. Burgart
  • P. A. Slepukhin
  • V. I. Saloutin
  • O. N. Chupakhin
  • M. A. Kravchenko
Full Articles

Abstract

A multi-component double Mannich cyclocondensation of 6-polyfluoroalkyl-2-thiouracils with formalin and heterocyclic amines (2-aminopyridine, 2-aminopyrimidine, 4-aminoantipyrine) proceeded regiospecifically at the C=S and NH centers giving rise to 3-hetaryl-8-polyfluoroalkylpyrimido[2,1-b][1,3,5]thiadiazines. The regioisomeric structure of the products was established by X-ray crystallography, IR and NMR spectroscopy, GLC-MS spectrometry. 6-Trifluoromethyl-2-thiouracil and 8-polyfluoroalkylpyrimido[2,1-b]thiadiazines exhibited weak tuberculostatic activity.

Key words

6-polyfluoroalkyl-2-thiouracil Mannich reaction formalin heterocyclic amines pyrimido[2,1-b][1,3,5]thiadiazines tuberculostatic activity 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • O. G. Khudina
    • 1
  • A. E. Ivanova
    • 1
  • Ya. V. Burgart
    • 1
  • P. A. Slepukhin
    • 1
  • V. I. Saloutin
    • 1
  • O. N. Chupakhin
    • 1
  • M. A. Kravchenko
    • 2
  1. 1.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation
  2. 2.Ural Research Institute of PhthisiopulmonologyMinistry of Healthcare and Social Development of the Russian FederationEkaterinburgRussian Federation

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