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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 906–912 | Cite as

The Mannich reaction in the synthesis of N,S-containing heterocycles 3. Unexpected direction of the aminomethylation reaction of N-methylmorpholinium 1-amino-2,4-dicyano-4-ethoxycarbonyl-1,3-butadienethiolate. One stage cascade synthesis of new derivatives of pyrido[1,2-a][1,3,5]triazine

  • V. V. Dotsenko
  • S. G. Krivokolysko
  • E. B. Rusanov
  • A. V. Gutov
  • V. P. Litvinov
Article

Abstract

The interaction of N-methylmorpholinium 1-amino-2,4-dicyano-4-ethoxycarbonyl-1,3-butadienethiolate with primary amines and formaldehyde leads to the formation of ethyl esters of 7-cyano-6-thioxo-1,3,4,6-2H-pyrido[1,2-a][1,3,5]triazine-9-carboxylic acid in place of the expected derivatives of pyrido[2,1-b][1,3,5]thiadiazine. The structure of the ethyl ester of 7-cyano-3-phenyl-6-thioxo-1,3,4,6-2H-pyrido[1,2-a][1,3,5]triazine-9-carboxylic acid was demonstrated by X-ray structural analysis.

Keywords

N-methylmorpholinium 1-amino-2,4-dicyano-4-ethoxycarbonyl-1,3-butadienethiolate pyrido-[1,2-a][1,3,5]triazines cascade heterocyclization Mannich reaction X-ray structural analysis 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. V. Dotsenko
    • 1
  • S. G. Krivokolysko
    • 1
  • E. B. Rusanov
    • 2
  • A. V. Gutov
    • 2
  • V. P. Litvinov
    • 3
  1. 1.ChemEx LaboratoryEast-Ukrainian Vladimir Dal National UniversityLuganskUkraine
  2. 2.Institute of Organic ChemistryNational Academy of Sciences of UkraineKiev
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscow

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