Chemistry of Heterocyclic Compounds

, Volume 28, Issue 9, pp 1048–1053 | Cite as

Synthesis, structure, and carbamoylation of 5-alkyl-N(1)-(β-hydroxyethyl)-4,5-dihydro-1,2,4-triazin-6-ones

  • A. F. Prokof'eva
  • Zh. S. Sapozhnikova
  • E. B. Putsykina
  • V. N. Volkova
  • N. N. Mel'nikov
Article
  • 23 Downloads

Abstract

The condensation of methyl α-(dimethylaminomethyleneamino)alkanoates with β-hydroxyethylhydrazine gave the isomeric N(1)- and N(2)-(β-hydroxyethyl)-5-alkyl-4,5-dihydro-1,2,4-triazin-6-ones. It was shown by IR spectroscopy that the products exist in the form of betaines both in solution and in the crystalline state. The reaction of the N(1) isomers with alkyl and aryl isocyanates leads to the formation of mono- or dicarbamoyl-substituted triazines. The preferred reaction path involves carbamoylation of the β-hydroxyethyl group.

Keywords

Spectroscopy Methyl Organic Chemistry Betaine Isocyanate 

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References

  1. 1.
    A. F. Prokof'ev, Zh. Z. Sapozhnikov, V. N. Volkova, V. V. Negrebetskii, L. A. Pokrovskaya, and N. N. Mel'nikov, Khim. Geterotsikl. Soedin., No. 7, 963 (1991).Google Scholar
  2. 2.
    E. C. Taylor and J. E. Macor, J. Heterocycl. Chem., No. 22, 409 (1985).Google Scholar
  3. 3.
    L. J. Bellamy, Infrared Spectra of Complex Molecules, Wiley, New York (1958).Google Scholar
  4. 4.
    H. E. Ungnade and L. W. Kissinger, J. Org. Chem., 23, 1794 (1958).Google Scholar
  5. 5.
    A. Camparini, A. M. Celli, and F. Ponticelli, J. Heterocycl. Chem., No. 15, 1271 (1978).Google Scholar
  6. 6.
    J. Saunders and K. Frisch, Chemistry of Polyurethanes [in Russian], Khimiya, Moscow (1968), p. 76, 86.Google Scholar
  7. 7.
    K. A. Nuridzhanyan, N. P. Bulanova, and L. M. Nesterova, Zh. Org. Khim., 6, 1589 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • A. F. Prokof'eva
    • 1
  • Zh. S. Sapozhnikova
    • 1
  • E. B. Putsykina
    • 1
  • V. N. Volkova
    • 1
  • N. N. Mel'nikov
    • 1
  1. 1.All-Union Scientific-Research Institute of Chemical Means for the Protection of PlantsMoscow

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